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Pinellas Gulf Beaches , STR Investment Guide 2026

Treasure Island, Florida
Short-Term Rental Rules and Investment Guide 2026

Florida's widest beach. The Gulf Coast's most unique STR zoning rule. A condo-hotel market no other Pinellas beach city can match. Everything a vacation rental investor needs to know before making an offer in Treasure Island.

No Minimum Stay in Resort Zones 937 Active STR Listings $35,205 Avg Annual Revenue Widest Beach in Florida ZIP Code 33706
Key Takeaways for Treasure Island STR Investors , 2026
Two rule sets govern every purchase: city zoning AND HOA documents. Five city zones (CG, RFM-30, RFH-50, PR-MU Core, PR-MU Gulf Boulevard) allow unlimited STR guest groups per year. RU-75 allows only 2 per year. RM-15 allows only 6. But city zoning is only the first question. The building's HOA governing documents (Declaration, Bylaws, Rules and Regulations) determine actual building-level rental rights and may be more restrictive. Never rely on a seller's or listing agent's verbal confirmation. Verify both. Source: City of Treasure Island, mytreasureisland.org, 2026; Florida Statute §718.503.
Three registrations required before your first booking. City Business Tax application, Florida DBPR Vacation Rental License (District 3, renews February 1), and Pinellas County TDT account. Total tax rate: 13% of gross revenue. Zero-return filings required even in months with no rental income. Source: mytreasureisland.org; taxcollect.com, 2026.
Occupancy is set by each building's governing documents, not a city ordinance cap. Treasure Island does not impose a specific per-unit guest cap through city ordinance for condos and condo-hotels. Maximum occupancy is determined by the Declaration of Condominium, Bylaws, and Rules and Regulations for each individual building. HOA rules may also be more restrictive than Florida Building Code. Review the governing documents for the specific building before purchasing , not the seller's representation of what the rules are.
48 condo and condo-hotel buildings identified from StellarMLS , zoning verification required for each. Buildings in CG, RFM-30, RFH-50, and PR-MU zones are STR-eligible. Buildings in RM-15 or RU-75 are not eligible for weekly rentals. Verify the zoning for any specific building with City of Treasure Island Community Development at (727) 547-4575 x230 before submitting any offer.
$35,205 average annual gross revenue. AirROI's 2026 dataset tracking 937 active Treasure Island listings (May 2025 to April 2026) shows $331 ADR, 39.8% average occupancy, and $129 RevPAR. Revenue grew 22.3% year over year. Top 10% earn $100,704-plus per year. Source: AirROI, May 2025 to April 2026.
The entire city is in a FEMA flood zone. Average elevation: three feet. Every purchase needs a FEMA 50% Rule status check post-Helene and Milton (2024). Flood insurance is effectively required on any mortgage. Under FEMA Risk Rating 2.0, an Elevation Certificate is no longer required to obtain an NFIP quote, but having one is valuable , it documents the property's specific elevation and helps you understand your full flood risk picture before closing. Get written insurance quotes before you close, not after. Source: Pinellas County Flood Maps, 2026.
Widest beach in Florida plus the Sunday drum circle. Up to 1,000 feet wide at Sunset Beach. The weekly drum circle and annual Sanding Ovations competition (November) are guest-demand anchors no neighboring city can replicate. John's Pass bridge at the northern boundary connects to Madeira Beach in 5 minutes.
March is peak; September is lowest. Peak season: December through April (snowbird season, spring break). Lowest: September (hurricane season, off-season). Plan reserve cash from peak months to cover September through October operating costs. Sanding Ovations in November drives shoulder-season bookings. Source: AirROI, May 2025 to April 2026.

Treasure Island STR Market , AirROI 2026 Data (May 2025 to April 2026, 937 Active Listings)

$35,205Avg Annual RevenueAirROI 2026
$331Avg Daily RateAirROI 2026
39.8%Avg OccupancyAirROI 2026
$129RevPARAirROI 2026
22.3%Revenue Growth YoYAirROI 2026
937Active ListingsAirROI 2026
61 daysAvg Booking Lead TimeAirROI 2026
MarchPeak Revenue MonthAirROI 2026

City Overview

Buying a Vacation Rental in Treasure Island Florida: What Investors Need to Know Before Making an Offer

What makes Treasure Island Florida a distinct vacation rental investment market?

Three things separate Treasure Island from every other Gulf Beach city for STR investors. First, the regulatory framework: Treasure Island is the only Florida Gulf Beach city that uses a change-of-occupancy system rather than a minimum stay rule, meaning properties in the five permitted zones can legally host nightly guests with no stay-length floor. Second, the demographics: the city has a 33.4% housing vacancy rate (U.S. Census 2020) , nearly one in three units is a second home or investment property. This is not a bedroom community that tolerates vacation rentals. It was built for them. Third, the condo-hotel inventory: Treasure Island has more designated condo-hotel buildings than any other Pinellas Gulf Beach city, which creates a separate investment tier with no equivalent elsewhere on the corridor. The city covers 5.3 square miles on a barrier island between the Gulf of Mexico and Boca Ciega Bay, ZIP code 33706, with John's Pass at its northern boundary and Blind Pass at its southern edge. Population 6,319, median age 62.1, average household income $157,000 , 44% above the Pinellas County average.

Source: Esri 2025; U.S. Census 2020; RPR Trade Area Report, May 2026.

Where did the name "Treasure Island" come from?

Around 1915, local property owners trying to boost real estate sales buried wooden chests on the beach and staged a fake discovery, generating newspaper coverage that spread the "Treasure Island" name across Florida. The stunt worked, the name stuck, and it became the official city name. The island was originally purchased by its first landholder, Tom Pierce, in 1908 for $1.25 per acre. One century later, Gulf-front parcels routinely trade above $1 million. Treasure Island was built to attract visitors from day one , and it still is.

Source: Wikipedia, citing historical records.

How did Treasure Island's canal neighborhoods get created?

The Great Gale of 1848, a catastrophic hurricane, carved out John's Pass at the northern tip of the island and simultaneously separated the sections that became Isle of Capri and Isle of Palms. The same storm that created the city's most iconic boat-access corridor also created two of its most coveted residential communities. In the 1950s, dredging operations using fill from Boca Ciega Bay created the canal lots that give Paradise Island its private-dock character today. Every era of Treasure Island's history left a physical fingerprint on the investment landscape buyers navigate in 2026.

Source: Wikipedia, citing historical records.

What makes Treasure Island different from other Pinellas Gulf Beaches for STR investors?

Six factors distinguish Treasure Island from every other Gulf Beach city for STR investors: the change-of-occupancy rule (a unique regulatory framework no other Florida Gulf Beach city uses), a beach up to 1,000 feet wide (the widest in Florida, a guest-experience differentiator no neighboring city can match), a deeper condo-hotel inventory than any other Pinellas Gulf Beach with different financing rules, three distinct neighborhoods each with its own guest demographic, the weekly Sunday drum circle at Sunset Beach, and the annual Sanding Ovations international sand-sculpting competition each November. AirROI's 2026 dataset tracking 937 active listings confirms 22.3% revenue growth year over year despite a 33.5% supply increase, meaning demand is outrunning new inventory.

Source: City of Treasure Island; AirROI, May 2025 to April 2026.

Treasure Island Beach Florida looking north showing the widest beach in Florida up to 1000 feet of white sand Gulf of Mexico shoreline with beachgoers and Gulf Boulevard vacation rental condo corridor in the background Pinellas County STR investment market
Treasure Island Beach looking north , up to 1,000 feet of white sand, the widest beach in Florida. This is the guest experience differentiator no neighboring city can replicate. Source: City of Treasure Island. Photo: Cyndee Haydon, Sandbars to Sunsets Team, Future Home Realty.

Where is Treasure Island located relative to major destinations?

Treasure Island is 5 minutes south of Madeira Beach (across John's Pass bridge), 5 minutes north of St. Pete Beach (across Blind Pass), 20 minutes from downtown St. Petersburg, 40 minutes from Tampa International Airport (TPA), and 45 minutes from St. Pete-Clearwater International Airport (PIE). Its Gulf Boulevard position makes it the geographic center of the Pinellas Gulf Beach corridor.

What is the buyer demographic in Treasure Island?

The dominant consumer segment (84.1% of households) is classified as "Silver and Gold" by Esri's Tapestry segmentation, characterized by a median net worth of $811,588, median household income of $102,652, 87% homeownership, and a median age of 64.4 years. These are high-wealth, mature buyers and renters who directly support the premium ADR that well-positioned STR properties command. A third of all housing units carry a seasonal vacancy classification, confirming the investment character of the market.

Source: RPR Trade Area Report, Esri 2025.

Proprietary Evaluation Framework

How Do You Evaluate a Treasure Island Short-Term Rental Investment? The Haydon SHORE™ Five-Factor Framework

Every Treasure Island STR evaluation starts with SHORE. Five factors, each applied specifically to what makes this city different from every other Gulf Beach market.

S
Supply & Demand

AirROI's 2026 dataset tracking 937 active Treasure Island listings shows 22.3% revenue growth year over year despite 33.5% supply growth, confirming demand is outrunning new inventory. Gulf-front units in RFH-50 zoning consistently outperform bay-side units. The condo-hotel concentration on Gulf Boulevard creates both the supply anchor and the demand anchor for the entire island market. Assess micro-location before assuming market-average performance is achievable for a specific unit.

H
Hosting & Rental Rules

Two separate rule sets govern every Treasure Island STR: what the city permits by zoning district, and what the individual building's HOA documents permit. Both must be verified. City zoning (CG, RFM-30, RFH-50, PR-MU) sets the outer boundary. The Declaration of Condominium, Bylaws, and Rules and Regulations set the actual building-level rules, which can be more restrictive. A building in an STR-permitted zone can still prohibit rentals, impose minimum stays, or cap the number of rentable units. Verbal representations from sellers or listing agents are not sufficient. Verify both the city zoning at (727) 547-4575 x230 and the complete governing documents before any offer. Source: City of Treasure Island, Chapter 68; Florida Statute §718.503.

O
Operating Economics

Market average gross revenue: $35,205 per year (AirROI, May 2025 to April 2026, 937 listings). Total tax rate: 13% of gross (6% FL sales tax, 1% Pinellas surtax, 6% TDT). Condo-hotel management fees run 20-40% of gross revenue. Coastal flood insurance in 2026 is $5,000 to $20,000 above pre-Helene 2024 levels for many Treasure Island properties. Get a written insurance quote before closing. Target 35-50% net margin for well-managed properties; condo-hotels typically net 25-40% due to higher management fees.

R
Risk & Resilience

Essentially the entire city sits in FEMA Zone AE or VE on a 3-foot barrier island. Every 2026 purchase needs two storm-specific items before closing: complete Helene and Milton damage assessment and repair permits, and FEMA 50% Rule status confirming how much improvement headroom remains (elevation costs run $150,000 to $400,000-plus when triggered). An Elevation Certificate is no longer required under FEMA Risk Rating 2.0 but is valuable to have , it documents the building's specific elevation relative to Base Flood Elevation and helps inform the insurance picture. Condo buildings 30 years or older require current Milestone Inspection and SIRS documentation. Source: FEMA; Pinellas County Flood Maps, 2026.

E
Experience & Earnings Potential

Treasure Island's experience premium comes from four verifiable factors: the widest beach in Florida (up to 1,000 feet), the weekly Sunday drum circle at Sunset Beach (a community tradition unlike anything on the Gulf Coast), Sanding Ovations each November (an international sand-sculpting competition driving shoulder-season demand), and John's Pass walking access from north Treasure Island. Top 10% of listings earn $100,704-plus per year at $490-plus ADR and 83-plus percent occupancy. The median closed condo sale price was $560,000 in April 2026 at a 96.3% median sale-to-list ratio. Always verify actual documented rental history for the specific unit, not platform projections. Source: AirROI, May 2025 to April 2026; StellarMLS, April 2026.

Sanding Ovations · Treasure Island · Every November  ·  sandingovationsmasterscup.com

Treasure Island is the only city in Florida officially designated the Sand Sculpture Capital of Florida. The annual Sanding Ovations international sand-sculpting competition draws named artists from around the world to Treasure Island Beach each November, generating some of the strongest shoulder-season booking demand on the Pinellas Gulf Beaches. For STR investors, this is a verified November demand driver that most neighboring city markets simply do not have.

Cyndee Haydon STR specialist Sandbars to Sunsets Team at the Sanding Ovations international sand sculpting competition entrance arch at sunset on Treasure Island Beach Florida Gulf Coast Pinellas County
Cyndee Haydon at Sanding Ovations, Treasure Island Beach
Official Sand Sculpture Capital of Florida designation for Treasure Island carved in sand at Sanding Ovations international sand sculpting competition Pinellas County Florida STR investment market
Treasure Island: the only city in Florida officially designated the Sand Sculpture Capital of Florida
Crowds walking among international sand sculptures at Sanding Ovations competition on Treasure Island Beach Florida with Gulf Boulevard vacation rental condo buildings in background Pinellas County
Festival crowds and sand sculptures at Sanding Ovations, Treasure Island Beach
Cyndee Haydon and Jack Haydon Gulf Beaches residents and property owners at Sanding Ovations standing in front of Merry Christmas from Treasure Island Florida sand sculpture Pinellas County
Cyndee and Jack Haydon at Sanding Ovations , residents who attend, not just experts who advise
Large crowd gathered at Sanding Ovations international sand sculpting competition at sunset on Treasure Island Beach Florida with Gulf of Mexico in background and sand sculptures visible , annual November event drives short-term rental demand on the Pinellas Gulf Beaches
Sanding Ovations draws thousands to Treasure Island Beach each November at sunset , this is what shoulder-season demand looks like. This crowd is booking nearby vacation rentals. Source: City of Treasure Island. Photo: Cyndee Haydon, Sandbars to Sunsets Team, Future Home Realty.

STR Rules Hub

Is Short-Term Rental Legal in Treasure Island Florida? The Change-of-Occupancy Rule, Permitted Zones, and What to Verify Before Any Offer

Yes. Short-term rentals are legal in Treasure Island, Florida in five zones: CG, RFM-30, RFH-50, PR-MU Core, and PR-MU Gulf Boulevard, with no minimum stay requirement and no limit on different guest groups per year. In RU-75 (single-family residential), only 2 different guest groups per year are allowed. In RM-15 (multi-family), only 6. Verify the specific parcel zone before any offer. Source: City of Treasure Island, Chapter 68, mytreasureisland.org, 2026.

The most common and most costly STR mistakes in Treasure Island come from misunderstanding the change-of-occupancy system. Every question below is one a real buyer or investor has asked. Every answer is direct and source-anchored.

"The change-of-occupancy rule is the most misunderstood STR regulation on the entire Gulf Coast. Buyers fall in love with a home in the Isle of Capri, then discover it's zoned RU-75 and can only host two different guest groups per year. That's a seasonal rental, not a short-term rental business. Knowing the zoning before you make an offer isn't optional, it's everything."
Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES | Broker Associate, Future Home Realty | Sandbars to Sunsets Team | Gulf Beaches Resident Since 1991

What are the short-term rental rules in Treasure Island, Florida?

Treasure Island regulates STRs through a change-of-occupancy system rather than a minimum stay rule. In the five STR-permitted zones (CG, RFM-30, RFH-50, PR-MU Core, PR-MU Gulf Boulevard), there is no limit on the number of different guest groups per year, allowing nightly and weekly rentals. In RU-75 (single-family residential), only 2 different guest groups per year are allowed. In RM-15 (multi-family residential), only 6 per year. Any property outside the permitted zones that is advertised for rental or exceeds the change-of-occupancy threshold is treated as an illegal Tourist Dwelling.

Source: City of Treasure Island, Chapter 68, mytreasureisland.org, 2026.

What is the Treasure Island change-of-occupancy rule and why does it matter?

Unlike most Gulf Beach cities that set a minimum stay length, Treasure Island limits the number of different guest groups that can occupy a property in a 12-month period. Each new set of visitors, paid or unpaid, counts as one change of occupancy. In RU-75, only 2 changes per year are permitted. In RM-15, only 6. In CG, RFM-30, RFH-50, PR-MU Core, and PR-MU Gulf Boulevard, there is no limit. This means a single zoning district determination changes an investment's entire income model.

Source: City of Treasure Island, Chapter 68, mytreasureisland.org, 2026.

Is there a minimum stay requirement for STRs in Treasure Island?

No. In the five permitted zoning districts, there is no minimum or maximum length of stay. A guest can book one night or one year. The restriction is on how many different guest groups use the property per year, not on the length of any individual stay. This no-minimum-stay framework, combined with the change-of-occupancy system, makes Treasure Island's STR regulations uniquely different from every other Pinellas Gulf Beach city.

Source: City of Treasure Island, mytreasureisland.org, 2026.

Which zoning districts do NOT allow short-term rentals in Treasure Island?

RU-75 (low-density single-family residential) and RM-15 (medium-density residential) do not allow true short-term rental operations. RU-75 is limited to 2 different occupant groups per year, and RM-15 is limited to 6. The Isle of Capri and Isle of Palms neighborhoods are primarily RU-75 and are not viable for weekly vacation rental investment regardless of what neighboring properties appear to be doing. Zoning enforcement is complaint-driven, and code violations can result in fines and mandatory cessation of rental activity.

Source: City of Treasure Island, Chapter 68, mytreasureisland.org, 2026.

Zoning District STR Eligibility at a Glance

ZoningDescriptionSTR StatusChanges Allowed Per YearInvestor Implication
CGCommercial GeneralSTR PermittedUnlimitedNightly and weekly rentals. Condo-hotel and mixed commercial uses typical.
RFM-30Resort Facilities MediumSTR PermittedUnlimitedPrimary zone for mid-density Gulf Boulevard condo-hotel buildings.
RFH-50Resort Facilities HighSTR PermittedUnlimitedHigh-density Gulf Boulevard. Highest guest-turnover potential.
PR-MU CorePlanned Redevelopment Mixed-Use CoreSTR PermittedUnlimitedConfirm specific building rules with Community Development.
PR-MU Gulf BlvdPlanned Redevelopment Mixed-Use Gulf BlvdSTR PermittedUnlimitedGulf Boulevard corridor. Full STR operation permitted.
RM-15Medium Density ResidentialRestricted6 per yearSeasonal rentals feasible. Weekly STR not eligible.
RU-75Low Density Single-FamilyNot STR Eligible2 per yearIsle of Capri, Isle of Palms. Seasonal only. Not viable for weekly STR.

Source: City of Treasure Island, Chapter 68 Land Development Regulations, mytreasureisland.org, 2026. Verify with Community Development at (727) 547-4575 x230 before any offer.

Verify Zoning Before Any Offer , This Is Non-Negotiable

Verbal representations from sellers, listing agents, or neighbors about STR eligibility are not sufficient. Contact Treasure Island Community Development at (727) 547-4575 x230 or visit mytreasureisland.org to confirm zoning before submitting any offer. Claiming Florida Homestead Exemption on a Tourist Dwelling triggers multiple years of back property taxes plus penalties from the Pinellas County Property Appraiser.

What licenses do I need to operate a short-term rental in Treasure Island?

Three registrations are required before the first booking: a City of Treasure Island Local Business Tax application filed at City Hall (120 108th Avenue), a Florida DBPR Vacation Rental License required if you rent the entire unit more than 3 times per year for periods under 30 days (Treasure Island is in DBPR District 3, renewing annually on February 1 with half-year fees beginning August 1), and a Pinellas County Tourist Development Tax account registered with the Pinellas County Tax Collector at (727) 464-7777. Monthly TDT remittance is required, with zero-return filings required even in months with no rental income.

Source: mytreasureisland.org; myfloridalicense.com; taxcollect.com, 2026.

What taxes do I owe on a Treasure Island STR and who collects them?

The total tax rate is approximately 13% of gross rental revenue: 6% Florida State Sales Tax, 1% Pinellas County Discretionary Surtax, and 6% Pinellas County Tourist Development Tax. Airbnb and Vrbo automatically collect and remit all three taxes for bookings made through their platforms. For direct bookings or platforms that do not collect Pinellas TDT, the owner registers and remits monthly to both the Florida Department of Revenue and the Pinellas County Tax Collector. TDT is due by the 20th of the following month. Late penalty: 10% of tax due or $50 minimum, whichever is greater, plus interest.

Source: Pinellas County Tax Collector; Florida Department of Revenue, 2026.

Does the Pinellas County STR Certificate of Use program apply in Treasure Island?

No. The Pinellas County STR Certificate of Use program, which requires a $150 safety inspection and $450 certificate fee renewed every two years, applies only to unincorporated Pinellas County. Treasure Island is an incorporated municipality with its own STR registration process. Verify current requirements directly with Treasure Island Community Development before applying for any county certificate. Source: mytreasureisland.org, 2026.

Treasure Island's Unique Asset Class

Should You Buy a Condo or a Condo-Hotel in Treasure Island Florida? Financing, Zoning, and Investment Returns Compared

What is a condo-hotel and how does it differ from a traditional condo in Treasure Island?

A condo-hotel is a building where individually owned units are operated as a hotel, complete with a front desk, daily housekeeping, and often a rental pool managed by a hotel company. Traditional condos are owner-managed; condo-hotels are professionally managed like hotels with the management structure built into the building's operating agreement. The financing difference is the most consequential for buyers: conventional Fannie Mae and Freddie Mac loans generally do not apply to condo-hotels because the buildings are classified as non-warrantable, requiring specialty portfolio lenders at higher rates and down payments.

How do I finance a Treasure Island condo-hotel?

Buyers need a specialty condotel portfolio loan (minimum 25% down payment, typically 1-2 percentage points higher rate than conforming loans, 6-12 months of reserves required) or a DSCR loan that qualifies based on the property's rental income rather than the buyer's personal debt-to-income ratio. All-cash purchases are common at higher price points. The most important step is to speak with a condotel-experienced lender before viewing any condo-hotel unit. Falling in love first and discovering the financing restriction after is the most expensive mistake in this specific market.

Source: Advancial Federal Credit Union, 2026.

What makes a condo non-warrantable and why does it matter for Treasure Island buyers?

A condo project is non-warrantable if it fails Fannie Mae and Freddie Mac guidelines, typically because more than 50% of units are non-owner-occupied, the building is operated as a hotel, a single owner controls more than 10% of units, the HOA is in litigation, or reserves are below 10% of the annual budget. Many Treasure Island condo-hotels trigger multiple criteria simultaneously. Non-warrantable status means conventional loans are unavailable, the resale buyer pool is narrower (limited to cash buyers or specialty lenders), and the transaction requires lenders who know this specific market.

Does the Treasure Island change-of-occupancy rule apply to condo-hotels?

No. Condo-hotels are typically located in CG, RFM-30, RFH-50, or PR-MU Core and PR-MU Gulf Boulevard zoning, where there are no restrictions on the number of changes of occupancy. That is precisely why they can operate as true hotels with nightly guest turnover. If a property being marketed as a condo-hotel is actually located in RU-75 or RM-15 zoning, that is a serious red flag requiring immediate zoning verification before proceeding. Source: City of Treasure Island, mytreasureisland.org, 2026.

How many days can I personally stay in my Treasure Island condo-hotel unit?

Owner-occupation of a condo-hotel unit is limited to a maximum of 90 days in any consecutive 12-month period under City of Treasure Island Code of Ordinances, Section 68-494(12). This is the city rule and applies regardless of what individual rental pool agreements say. A more restrictive rental pool agreement (such as 14 or 30 owner nights) takes precedence over the city rule, but no rental pool agreement can allow more than the city's 90-day maximum. The unit must be available to the general public for rental for the remaining 275-plus days of the year. The city may require affidavits of compliance and can inspect books and records to confirm adherence (Sec. 68-494(13,14)).

Source: City of Treasure Island Code of Ordinances, Sec. 68-494(12), Ord. No. 15-03, § 3, 7-7-15.

What happens if my Treasure Island condo-hotel unit has fewer than 6 different guest groups per year?

This is the opposite of the residential zone change-of-occupancy rule and one of the most misunderstood compliance points in Treasure Island. Under City of Treasure Island Code Section 68-494(1), if a condo-hotel unit does not change occupancy more than 6 times in any consecutive 12-month period, a rebuttable presumption arises that the unit is NOT being operated as a transient accommodation. The city can then presume the owner is out of compliance with the condo-hotel regulations. In residential RU-75 zones, 2 changes is the maximum allowed. In a condo-hotel, at least 6 changes per year is effectively the minimum required to maintain transient use status. Condo-hotel owners must maintain active rental activity to preserve their commercial transient designation.

Source: City of Treasure Island Code of Ordinances, Sec. 68-494(1), Ord. No. 05-09, § 3, 4-12-05.

What operational requirements does Treasure Island impose on condo-hotel units beyond zoning?

Beyond the change-of-occupancy and owner-occupation rules, the City of Treasure Island Code Section 68-494 imposes six additional operational requirements on all condo-hotel units. A reservation system is required as an integral part of the facility (Sec. 68-494(3)). A lobby and front desk area must be operated as a conventional hotel lobby would be operated (Sec. 68-494(4)). All units except the resident manager unit must be included in the rental inventory and available to the general public (Sec. 68-494(8)). An annual occupational license from the city is required for each individual unit (Sec. 68-494(10)). Signage visible to the public designating the use as a hotel, motel, or transient accommodation is required (Sec. 68-494(11)). Units cannot be homesteaded or used for home occupational licensing (Sec. 68-494(6)). Buyers should confirm all operational requirements are currently being met before closing.

Source: City of Treasure Island Code of Ordinances, Sec. 68-494, Ord. No. 05-09 (2005), Ord. No. 06-02 (2006), Ord. No. 15-03 (2015).

How do I verify the actual rental rules for a specific Treasure Island condo or condo-hotel building?

The only reliable source is the building's own governing documents. Not the seller. Not the listing agent. Not a neighbor's experience. City zoning tells you what the city permits in that district. The HOA documents tell you what that specific building actually allows, and those are two completely different questions with two different answers. The more restrictive rule controls, and after closing you cannot undo what the documents say.

For every Treasure Island condo and condo-hotel purchase, request and read the complete Declaration of Condominium, Bylaws, Rules and Regulations, and all amendments before submitting an offer. These documents will confirm: whether short-term rentals are permitted at all; whether the building imposes a minimum stay longer than what the city requires; whether a rental cap limits what percentage of units can be rented at the same time; whether there is an owner waiting period before rentals can begin; whether board approval of tenants or a rental application process is required; and, for condo-hotels, the specific terms of the rental pool agreement including revenue splits, management fees, owner usage windows, and blackout restrictions. Florida Statute Section 718.503 gives buyers a seven business day review period for condo documents after receipt. Use every day of it.

Source: Florida Statute §718.503, effective July 1, 2025; City of Treasure Island Code of Ordinances, Sec. 68-494; standard Florida real estate due diligence practice.

HOA Documents, Not Seller Representations, Determine Your Rental Rights

Every building on the Treasure Island condo and condo-hotel list has its own governing documents that set the actual rental rules for that building. Those rules may be identical to what the city allows, or they may be significantly more restrictive. A building in an RFM-30 zone can still prohibit STRs entirely if the HOA documents say so. A seller or listing agent telling you "this building allows short-term rentals" is not sufficient. The Declaration, Bylaws, and Rules and Regulations are the only documents that count. Review them before you offer, not after.

48 Confirmed STR-Eligible Buildings · StellarMLS May 2026 · 10 Designated Condo-Hotel

Building Address Type Yr Built MLS Price Data
Blind Pass Lagoons Condo 9815 Harrell Ave, Treasure Island Condo 1981 Active · $432,000
Boca Ciega Shores Condo 245 104Th Ave, Treasure Island Condo 1968 Active · $339,900
Capri Isle Garden 250 126Th Ave, Treasure Island Condo 1967 Active · $324,900
Capri Lighthouse Condo 220 126Th Ave, Treasure Island Condo 1961 Active · $620,000
Capri Townhome Condominium 11605 1St St E, Treasure Island Condo 2026 Active · $1,750,000
Carefree Apts Condo 9895 1St St E, Treasure Island Condo 1960 Active · $199,900
Copa Palms Condo 11440 1St St E, Treasure Island Condo 1969 Active · $299,900
Crystal Palms Bch Resort At Treasure Island Condo 11605 Gulf Blvd, Treasure Island Condo 2008 Active · $359,900
Gulf Spray Condo 7797 W Gulf Blvd, Treasure Island Condo-Hotel 1951 Active · $524,900
Harbor House Condos 8465 W Gulf Blvd, Treasure Island Condo 1974 Active · $329,900
Harborview Condo 11605 3Rd St E, Treasure Island Condo 1973 Active · $549,000
Island Inn Condo 9980 Gulf Blvd, Treasure Island Condo-Hotel 1976 Active · $448,000
Lagoon Lane Condo 11901 Lagoon Ln, Treasure Island Condo 1981 Active · $524,000
Leporello Condo Residence 12100 Capri Cir S, Treasure Island Condo 1969 Active · $314,498
Mansions By The Sea Condo 7650 Bayshore Dr, Treasure Island Condo 1980 Active · $995,000
Pearl 10126 Gulf Blvd, Treasure Island Condo 2025 Active · $4,800,000
Sun Ketch Condo 228 Sun Vista Ct N, Treasure Island Condo 1988 Active · $399,000
Sunset Cove Condo 8565 W Gulf Blvd, Treasure Island Condo 1972 Active · $299,000
Sunset Vistas Condo Hotel On The Gulf 12000 Gulf Blvd, Treasure Island Condo-Hotel 2006 Active · $599,000
Tides Of Capri East Condo 12055 3Rd St E, Treasure Island Condo 1984 Active · $385,000
Treasure Island Villas Condo 10365 Paradise Blvd, Treasure Island Condo 1968 Active · $149,900
Treasure Sands Condo 11000 Gulf Blvd, Treasure Island Condo 1974 Active · $599,000
Tropic Terrace Apt 11730 Gulf Blvd, Treasure Island Condo-Hotel 1950 Active · $259,900
Westwind Condo Apts 9715 Harrell Ave, Treasure Island Condo 1975 Active · $219,926
Bahia Mar At Treasure Island Condo 10133 Gulf Blvd, Treasure Island Condo 2007 Pending · $990,000
Lands End At Sunset Beach Condo 7564 Bayshore Dr, Treasure Island Condo 1985 Pending · $737,000
12080 Capri Circle South Condo The 12080 Capri Cir S, Treasure Island Condo 1979 $394,000 · sold 03/21/2
Amadeus Condo 145 104Th Ave, Treasure Island Condo 1996 $550,000 · sold 06/11/2
Bay Breeze Condo 10109 Gulf Blvd, Treasure Island Condo 1985 $850,000 · sold 04/19/2
Beach Villas Of Treasure Island 10280 Gulf Blvd, Treasure Island Condo 1960 $385,000 · sold 03/06/2
Bilmar Beach Resort Condo 10650 Gulf Blvd, Treasure Island Condo-Hotel 1974 $345,000 · sold 06/30/2
Capri Mnr Condo 12005 3Rd St E, Treasure Island Condo 1968 $390,000 · sold 10/30/2
Club Capri Condo 175 116Th Ave, Treasure Island Condo 1980 $340,000 · sold 09/19/2
Del Mar At Sunset Beach Condo 8408 Bayshore Dr, Treasure Island Condo 2008 $1,500,000 · sold 10/30/2
Gulf Sounds On Treasure Island Condo 12240 Gulf Blvd, Treasure Island Condo-Hotel 1950 $535,000 · sold 09/06/2
Gulf To Bay Lagoons Condo 10301 Gulf Blvd, Treasure Island Condo 1982 $550,000 · sold 02/06/2
Gulls Nest Condo 11701 1St St E, Treasure Island Condo 1972 $309,000 · sold 01/03/2
Herons Landing Condo 11045 3Rd St E, Treasure Island Condo 1964 $185,000 · sold 04/02/2
Malyn Condo Motel Condo 282 Treasure Island Cswy, Treasure Island Condo-Hotel 1961 $320,000 · sold 01/21/2
Ocean Club 11500 Gulf Blvd, Treasure Island Condo-Hotel 2022 $810,000 · sold 09/20/2
Oceana At Treasure Island Condo 10116 Gulf Blvd, Treasure Island Condo-Hotel 2018 $984,000 · sold 11/26/2
Outrigger The Condo 283 104Th Ave, Treasure Island Condo 1968 $250,000 · sold 07/12/2
Palms At The Pass Condo 107 127Th Ave, Treasure Island Condo 1981 $1,050,000 · sold 07/22/2
Porto Fino Condo 143 94Th Ave, Treasure Island Condo 1974 $510,000 · sold 08/21/2
Sunset Chateau Condo 8470 W Gulf Blvd, Treasure Island Condo 1974 $340,000 · sold 12/16/2
Sunset Cove Condo South Bldg 8565 W Gulf Blvd, Treasure Island Condo 1972 $315,440 · sold 04/11/2
Surf Beach Resort Condo 11040 Gulf Blvd, Treasure Island Condo-Hotel 2005 $740,000 · sold 03/29/2
Yum Yum Tree The Condo 8200 Bayshore Dr, Treasure Island Condo 1964 $375,000 · sold 04/22/2

Source: StellarMLS, active, pending, and closed transactions, Treasure Island FL 33706, May 2026. Condo-Hotel designation from StellarMLS. City zoning and HOA documents must be verified independently before any offer. Cyndee Haydon, Future Home Realty, (727) 710-8035. This is a Comparative Market Analysis, not a formal appraisal.

Condo vs. Condo-Hotel: Side-by-Side Comparison

FactorTraditional CondoCondo-Hotel (Condotel)
FinancingConventional available (if warrantable)Specialty condotel loan only, min 25% down
Interest rateMarket conforming rateTypically 1-2% higher than conforming
Owner self-management of STRYesRarely, usually hotel management required
Front desk and housekeepingNoYes, hotel-style operations
Owner usage restrictionPer HOA onlyMaximum 90 days per consecutive 12-month period (Sec. 68-494(12), City of Treasure Island Code). HOA rental pool agreements may impose stricter limits.
Change-of-occupancy ruleDepends on zoningNo restriction (CG, RFM-30, RFH-50, PR-MU)
Management fee15-25% if professionally managed20-40% of gross revenue
Resale buyer poolBroaderNarrower, cash or condotel-specialty financing
Get Condotel Financing Pre-Qualified Before Your First Showing

Falling in love with a Treasure Island condo-hotel and then discovering your financing does not apply is the most expensive and most common mistake in this specific market. Contact Cyndee at (727) 710-8035 before viewing any condo-hotel unit to connect with a condotel-experienced lender who can pre-qualify you in 48 hours.

Flood Zones and Storm Resilience

Treasure Island Flood Zones, Hurricane Helene and Milton, and the FEMA 50% Rule: What Every 2026 Buyer Must Know

Is Treasure Island in a flood zone?

Yes. Essentially the entire city of Treasure Island sits in FEMA-mapped Special Flood Hazard Areas. Most parcels are in Zone AE (1% annual chance flood) or Zone VE (1% annual chance flood with wave action, typically the Gulf-facing strip). The island averages three feet of elevation above sea level. Flood insurance is effectively required on any property with a mortgage and is strongly recommended even on cash purchases. Check the FEMA Flood Map Service Center at msc.fema.gov or Pinellas County's interactive flood map at pinellas.gov/flood-maps-zones for any specific address. Under FEMA Risk Rating 2.0, an Elevation Certificate is no longer required to obtain an NFIP flood insurance quote, but having one ($300-$700 if not already on file) is valuable , it documents the property's specific elevation relative to Base Flood Elevation and helps you understand your full flood risk before closing.

Source: FEMA Flood Map Service Center; Pinellas County Flood Maps, 2026.

What happened in Treasure Island during Hurricanes Helene and Milton in 2024?

Hurricane Helene struck on September 26, 2024 and sent what the City of Treasure Island described as "a wall of water across" the island, flooding beachfront condos and single-family homes and rendering multiple STRs temporarily inoperable. Hurricane Milton followed 13 days later on October 9, 2024, compounding the damage before recovery was complete. Multiple condo-hotel buildings sustained significant ground-floor water intrusion. For every Treasure Island property purchase in 2026, buyers must obtain three things in writing: the documented damage assessment from both storms, all permits pulled for post-storm repairs, and the FEMA 50% Rule status confirming how much improvement headroom remains.

Source: City of Treasure Island Facebook, September 2025; 10 Tampa Bay, 2024.

What is the FEMA 50% Rule and how does it affect Treasure Island purchases?

The FEMA 50% Rule states that if a property in a Special Flood Hazard Area is improved or repaired by more than 50% of its pre-improvement market value (excluding land), the entire structure must be elevated to current floodplain code. Pinellas County requires an additional one-foot freeboard above base flood elevation. After Helene and Milton, many Treasure Island properties are at or approaching this threshold. Elevation costs typically run $150,000 to $400,000 or more. Buyers must request the complete city permit history and any damage assessments from the seller before submitting any offer.

Source: FEMA; Pinellas County, 1-foot freeboard requirement.

Should I buy a Treasure Island property that flooded in Hurricane Helene or Milton?

Possibly, with complete documentation and eyes-open underwriting. Three questions determine the answer: Are repairs fully permitted and completed with documented inspections? Has the FEMA 50% Rule been triggered, and if so, was the property properly elevated? What does the post-repair insurance picture look like in terms of premiums, deductibles, and available coverages? A properly repaired and elevated post-storm property at a storm discount can be a strong investment, but only with verified answers to all three questions before closing.

What insurance does a Treasure Island STR owner need?

As Cyndee Haydon, who serves as 2026 Chair of the NAR Regulatory Issues Forum and has tracked coastal insurance trends across the Gulf Beaches, confirms: STR owners need six coverage types. An STR-specific dwelling policy covering commercial rental activity (standard homeowner policies typically exclude it). Wind and hurricane coverage, often a separate policy. NFIP or private flood insurance with a 30-day waiting period unless tied to a home purchase. Liability coverage of at least $1 million to $2 million. Loss-of-rent coverage for income replacement during covered-loss repairs. For condos, a unit owner policy written for transient rental use. Written insurance quotes before closing are essential: coastal premiums in 2026 are $5,000 to $20,000 above pre-Helene levels for many Treasure Island properties.

Source: Balmaseda and Associates; standard Florida coastal insurance practice, 2026.

StellarMLS Market Data

How Much Does a Vacation Rental Condo Cost in Treasure Island Florida? April 2026 Market Report

StellarMLS data for April 2026, Treasure Island condominiums and condo-hotels only. This is STR-investor-relevant inventory, not all Treasure Island property. Source: StellarMLS, April 2026, presented by Cyndee Haydon, Future Home Realty. This is a market opinion and not a formal appraisal.

54Active Listings
6Pending
9April 2026 Closings
95.3%Avg Sale-to-List

What did Treasure Island condos sell for in April 2026?

StellarMLS data for April 2026 shows nine Treasure Island condominiums and condo-hotels closing with a median sale price of $560,000, a median sale-to-list ratio of 96.3%, and a median of 34 days on market. The average sale-to-list ratio of 95.3% confirms sellers are achieving near-asking prices in a functioning market. The closed price range ran from $185,000 for a 1-bedroom non-Gulf unit to $979,000 for a new-build resort condo. Source: StellarMLS, April 2026, presented by Cyndee Haydon, Future Home Realty.

April 2026 Closed Sales , 9 TransactionsValue
Median Sale Price$560,000
Median List Price$599,900
Median Sale-to-List Ratio96.3%
Average Sale-to-List Ratio95.3%
Median Days on Market34 days
Average Days on Market85 days
Fastest Sale1 day (Westwind, $243,000, 100%)
Slowest Sale324 days (Ocean Club condo-hotel, $979,000, 98%)
Closed Price Range$185,000 to $979,000
Median Price Per Sq Ft$424
Active Listings54 (median list $524,450)
Pending6 (median list $718,000)
Absorption Rate~6 months of supply

Source: StellarMLS, April 2026, Treasure Island FL 33706, condominiums and condo-hotels. Cyndee Haydon, Future Home Realty, (727) 710-8035. This is a Comparative Market Analysis and should not be considered a formal appraisal.

All 9 April 2026 Closings , What Each Sale Tells Investors

Property Sold SP/LP Days Investor Note
Westwind Condo #9
9715 Harrell Ave		 $243,000 100% 1 No contingency. Full price in one day. This is what correct pricing looks like.
Lands End at Sunset Beach #303
7467 Bayshore Dr		 $825,000 97.6% 6 Sunset Beach Intracoastal. 6 days to contract. The Sunset Beach premium is real and verified.
Treasure Sands #702
11000 Gulf Blvd		 $650,000 96.3% 23 Gulf Boulevard mid-island. Under contract in 23 days at 96 cents on the dollar.
Herons Landing #6
11045 3rd St E		 $185,000 100%* 24 *Original ask was $299,999. Sold at 62 cents on the dollar vs OLP. Reached price reality after 24 days at $185K.
Mansions by the Sea #204
7600 Bayshore Dr		 $700,000 94.0% 34 Bayshore Drive Intracoastal. 34 days, normal negotiation, clean close.
Gulf to Bay Lagoons #302
10301 Gulf Blvd		 $560,000 93.3% 77 Mid-market unit, 77 days. 7% negotiation room. This is the median sale for April.
Tides of Capri West #108
11650 Capri Cir S		 $399,000 93.0%* 138 *Original ask $479,000 , SP/OLP was 83%. 138 days and a 17% price correction to close.
Treasure Island Villas #58
10369 Paradise Blvd		 $204,500 85.6% 141 Largest discount in April. Entry-level non-Gulf unit needed 14% off list to move after 141 days.
Ocean Club Condo-Hotel #513 CONDO-HOTEL
11500 Gulf Blvd		 $979,000 98.0% 324 The only condo-hotel to close in April. Sat 324 days , but closed at 98% of asking. Patient sellers win in the condo-hotel segment. Portfolio lenders required.

Source: StellarMLS, April 2026. SP/OLP = sale price to original list price ratio. Presented by Cyndee Haydon, Future Home Realty. This is a Comparative Market Analysis and should not be considered a formal appraisal.

What is the price range of active Treasure Island condo listings in 2026?

As of May 2026, the 54 active Treasure Island condo and condo-hotel listings range from $149,900 for a studio or 1-bedroom non-Gulf unit to $4,995,000 for new-construction penthouse units at The Pearl on Gulf Boulevard. The median active list price is $549,000. Condo-hotel units cluster between $360,000 and $999,000 along Gulf Boulevard. Source: StellarMLS, May 2026.

"In April 2026, Treasure Island condos were selling at 96 cents on the dollar with a median of 34 days on market. That's not a distressed market. That's a market with real buyers making calculated decisions. The sellers who moved were prepared, and the buyers who won were pre-qualified."
Cyndee Haydon | Future Home Realty | StellarMLS April 2026, presented by Cyndee Haydon

Neighborhood Guide

Sunset Beach, Mid-Island, or North Island: Which Treasure Island Neighborhood Produces the Best Vacation Rental Returns?

Each of Treasure Island's three neighborhoods targets a different investor profile. Sunset Beach draws repeat guests and longer stays anchored by the Sunday drum circle. Mid-Island Gulf Boulevard is the central resort strip anchored by Sanding Ovations and the Treasure Island Beach Trail. North Island, including Isle of Capri and Paradise Island, benefits from John's Pass walkability and waterfront canal access. Source: AirROI 2026; StellarMLS, May 2026.

What are the main STR-eligible neighborhoods in Treasure Island?

Three Treasure Island neighborhoods are viable for STR investment: Sunshine Beach (north end, near John's Pass), Mid-Island Beach (central Gulf Boulevard resort strip, highest condo-hotel concentration), and Sunset Beach (south end, home to the Sunday drum circle and Ka'Tiki). The Isle of Capri, Isle of Palms, and Paradise Island neighborhoods are primarily RU-75 zoning, limiting them to 2 changes of occupancy per year and making them unsuitable for weekly STR operation.

Sunshine Beach

North Treasure Island, closest to John's Pass bridge and Madeira Beach. Mix of mid-rise condos and residential properties. Quieter than Sunset Beach, with strong year-round demand from guests wanting John's Pass Village access without the central resort atmosphere. Solid mid-market price point relative to the island.

John's Pass AccessMid-Rise Condos
Mid-Island Beach

Central resort strip anchored around Gulf Boulevard and 107th Avenue. Home to the city's largest condo-hotel buildings: Crystal Palms BCH Resort, Sunset Vistas Condo Hotel, Oceana at Treasure Island, and Treasure Sands. Walking access to restaurants and the Treasure Island Beach Trail. Anchor location for Sanding Ovations each November.

Condo-Hotel HubSanding Ovations
Sunset Beach

South end near Blind Pass. The most culturally distinct and walkable beach neighborhood on the island. Ka'Tiki, Sea Dog Brewing Co., Caddy's on the Beach, and the weekly Sunday drum circle make this the Old Florida beach experience guests cannot find anywhere else. Smaller-scale homes and cottages at premium rates relative to unit size.

Sunday Drum CircleKa'Tiki Anchor

Should I buy on the Gulf side or the bay side of Treasure Island?

Gulf side (Sunshine, Mid-Island, and Sunset Beach): higher ADR, beachfront premium, more demand, STR-friendly zoning in most buildings, higher entry price and insurance costs. Bay side (Isle of Capri, Isle of Palms, Paradise Island): beautiful canal communities with boat slips and dock potential, lower purchase price, but primarily RU-75 zoning that permits only 2 changes of occupancy per year. Bay-side Treasure Island is excellent for owner-occupied properties or long-term seasonal rentals, and not viable for weekly STR investment.

Is Treasure Island a better STR investment than Madeira Beach?

They serve different investment profiles. Treasure Island wins on the widest beach in Florida (up to 1,000 feet), deeper condo-hotel inventory, and the Sunset Beach cultural anchor. Madeira Beach wins on walkability (John's Pass Village is a true pedestrian district), stronger entertainment density, and higher ADR potential on premium single-family properties. As the top-rated vacation rental specialist on the Gulf Beaches, Cyndee's view is that the strongest portfolio position is to own one of each, with John's Pass as the geographic and experiential connection between them.

Buyer FAQ and Revenue Benchmarks

How Much Can You Earn From a Treasure Island Florida Short-Term Rental? Revenue Data and Buyer Questions Answered

Treasure Island vacation rentals averaged $35,205 in annual gross revenue in 2026 at a $331 average daily rate and 39.8% occupancy across 937 active listings. Revenue grew 22.3% year over year. Top 10% of listings earned $100,704 or more per year. Sanding Ovations drives measurable November demand when most Gulf Beach markets are soft. Source: AirROI 2026, May 2025 to April 2026.

How much can I earn from an Airbnb in Treasure Island, Florida?

AirROI's 2026 dataset, which tracks 937 active Treasure Island listings across Airbnb and Vrbo from May 2025 through April 2026, shows $35,205 in average annual gross revenue at a $331 average daily rate and 39.8% average occupancy. Top-performing listings (top 10%) earn over $8,392 per month at $490-plus ADR and 83-plus percent occupancy. March is the peak revenue month; September is the lowest.

Source: AirROI, May 2025 to April 2026, 937 active Treasure Island listings.

What is the smartest STR investment under $500,000 in Treasure Island?

A 1-2 bedroom condo or condo-hotel unit in an RFM-30 or RFH-50 zoned building, ideally Gulf-front or one block back, with HOA-confirmed STR eligibility. Underwrite conservatively at $35,205 market average annual revenue (AirROI 2026) and target top-quartile performance within 18 months through pricing optimization, strong amenity setup, and professional listing photography.

What is the number one mistake Treasure Island STR investors make?

Buying in RU-75 or RM-15 zoning assuming weekly short-term rentals are permitted because neighboring properties appear to operate that way. The change-of-occupancy rule is enforceable through code complaints, and claiming Florida Homestead Exemption on a Tourist Dwelling triggers back property taxes plus penalties. Verify zoning at (727) 547-4575 x230 before any offer. Source: City of Treasure Island, mytreasureisland.org, 2026.

What is the number one mistake Treasure Island condo-hotel investors make?

Not pre-qualifying with a condotel-experienced lender before making an offer. The financing falls through at underwriting, the deal collapses, and the buyer loses deposit money and months of opportunity cost. Talk to a condotel-experienced lender before viewing any condo-hotel unit in Treasure Island.

What is the typical net income on a Treasure Island STR after all expenses?

At median performance, roughly 35-50% of gross revenue lands as net income after taxes (13%), insurance, HOA, utilities, cleaning, management, supplies, and maintenance. Top operators push to 55% or more through pricing optimization and strong reviews. Condo-hotels typically net lower, often 25-40% of gross, because of higher management fees (20-40% of revenue).

What is the seasonality pattern for Treasure Island STRs?

AirROI's 2026 dataset tracking 937 active Treasure Island listings shows March as the single highest-revenue month, with peak season running December through April. Summer (May through August) brings strong family-vacation occupancy. September is the lowest revenue month. The Sunday drum circle and Sanding Ovations in November provide Treasure Island with shoulder-season demand anchors that most neighboring cities lack. Budget reserve cash from peak months to cover September through October operating costs. Source: AirROI, May 2025 to April 2026.

Can I do a 1031 exchange on a Treasure Island STR?

Yes. STRs held as investment properties qualify for Section 1031 like-kind exchange. The strict timelines apply: 45 days to identify the replacement property and 180 days to close. A qualified intermediary must hold the sale proceeds. Consult a CPA before listing if a 1031 is part of the plan. 1031 buyers often pay slightly more and close faster because they are working under deadline pressure.

How Much Do Treasure Island Airbnbs Actually Earn? Performance Tiers by Quartile

Top 10%
$100,704+/yr
$8,392+/month
$490+ ADR
83%+ occupancy
Top 25%
$67,488+/yr
$5,624+/month
$355+ ADR
66%+ occupancy
Market Average
$35,205/yr
$2,934/month
$331 ADR
39.8% occupancy
Bottom 25%
$20,748/yr
$1,729/month
$196 ADR
20% occupancy

Source: AirROI, May 2025 to April 2026, 937 active Treasure Island listings. Individual property performance varies by location, unit size, building quality, management, and amenities. These are market benchmarks, not projections for any specific property.

Seller Guide

How Do You Sell an Active Vacation Rental in Treasure Island Florida? What STR Sellers Need to Know in 2026

The highest-value Treasure Island STR sales are structured as going-concern transfers, where the Airbnb or Vrbo listing, review history, and booking calendar transfer with the property. A Treasure Island condo with documented Sanding Ovations bookings and $35,000 to $50,000 annual income is a categorically different asset than a vacant unit with identical finishes. No yard sign, targeted investor outreach, and documented income are the three elements that close at full price. Source: Cyndee Haydon, 150-plus STR transactions.

What documents should I have ready before listing my Treasure Island STR for sale?

Sellers who walk in organized close faster and negotiate from strength. Prepare: Schedule E tax returns and 12-24 months of verified rental revenue statements, all permits and documentation for any Helene and Milton storm repairs, an Elevation Certificate if you have one (valuable but no longer required under FEMA Risk Rating 2.0 , buyers will appreciate having it), HOA documents including financials and reserve study, the Florida DBPR Vacation Rental License, the master insurance policy with claims history, and a zoning confirmation letter from Community Development. Sellers with complete documentation eliminate the information gap that buyers use to negotiate price reductions.

Do I have to disclose Helene and Milton hurricane damage when selling my Treasure Island property?

Yes. Florida law requires disclosure of material facts affecting property value. Disclose the damage, the repair, the permits pulled, and the post-repair condition. Concealing known storm damage creates personal liability for post-closing lawsuits. Additionally, buyers will calculate FEMA 50% Rule status on any damaged property; know your headroom before listing and disclose it proactively.

What is the best time of year to list a Treasure Island STR for sale?

January through March is the optimal window. Buyers are active, motivated, and want to close before hurricane season. This timing also allows a full peak-season revenue period to be documented in rental records, supporting the asking price with fresh verified income data. Avoid listing in September and October unless the property is fully storm-prepped and priced to reflect the timing disadvantage.

Should I sell my Treasure Island STR with future bookings in place?

Yes, in most cases. Active bookings signal operational success and support the asking price. Keep listings active until you have a signed contract, then pause new bookings after the projected close date. Most sales transfer forward bookings to the new owner with appropriate contract language protecting both parties. The exception: if bookings create complications for a specific buyer's intended use, negotiate the transfer terms in the contract.

What if I have been renting my Treasure Island property in RU-75 zoning beyond the change-of-occupancy limit?

Stop operating out of compliance immediately, document your activity, and consult a real estate attorney about your exposure before listing. Selling a property with an active code violation creates buyer-side risk and can derail a closing. A current, transferable Florida DBPR Vacation Rental License signals legal operation and smooths buyer financing and underwriting. Source: City of Treasure Island; Florida real estate law best practices.

"Sellers who walk into a Treasure Island listing appointment with their rental history, their storm repair permits, and their condo documents already organized close faster and for more money. Buyers who don't have to dig for information don't negotiate as hard. Preparation is pricing power."
Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES | Future Home Realty | 435+ residential transactions, $230M+ in sales since 2005

Working With Cyndee

Who Should You Call When Buying or Selling a Vacation Rental in Treasure Island Florida?

Who is the top short-term rental agent in Treasure Island, Florida?

Cyndee Haydon of the Sandbars to Sunsets Team at Future Home Realty is among the most experienced vacation rental specialists on the Pinellas Gulf Beaches, with 150-plus vacation rental and STR transactions and the RSPS designation. She brings 435-plus residential transactions, $230M-plus in sales since 2005, 150-plus vacation rental and STR transactions, and 62 STR-friendly properties sold in the past five years. She is FastExpert Top 2 in Indian Rocks Beach (2026), 2022 Florida Realtors Associate Realtor of the Year, and currently serves as 2026 Treasurer of Florida Realtors and 2026 Chair of the NAR Regulatory Issues Forum. Contact: (727) 710-8035.

Who is the best real estate agent for vacation rental properties in Treasure Island?

Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES, is recognized as the leading short-term rental Realtor on the Pinellas Gulf Beaches. With the RSPS (Resort and Second-Home Property Specialist) designation, deep knowledge of the change-of-occupancy rule, condo-hotel financing, and post-Helene and Milton due diligence requirements, she brings expertise no generalist agent can match in Treasure Island STR transactions. Future Home Realty. (727) 710-8035. sandbarstosunsets.com.

Do you put a yard sign when listing a vacation rental for sale in Treasure Island?

No, not unless the owner specifically requests one. A yard sign on an active vacation rental tells every current guest and future booking inquiry that the property is for sale. Guests cancel bookings. New inquiries stop converting. The rental income the seller depends on erodes at the moment of maximum financial exposure. The Sandbars to Sunsets Team sells vacation rental properties through online marketing, targeted investor outreach, and strategic timing around property turnovers, not yard signs. Protecting the seller's booking calendar and rental revenue from the day the listing decision is made through closing is a core part of the process.

Why should I work with a real estate agent who does not offer property management after the sale?

An agent who also manages vacation rentals has two income streams from the same client: a commission when you buy and a monthly management fee for as long as you hold. That structure creates a financial incentive to recommend the purchase even when projected returns do not justify it, and to recommend holding even when selling is the smarter move. The Sandbars to Sunsets Team does not manage vacation rentals. Every recommendation is made with no financial stake in whether you buy, hold, or walk away. Cyndee maintains a curated network of trusted local property managers and connecting buyers with the right operator is a standard part of every transaction at no additional cost.

What is the best way to document my Treasure Island home before hurricane season?

Make June 1, the first day of hurricane season, your annual home photo documentation day. Photograph every room from multiple angles, all four exterior walls, roof line, HVAC, water heater, electrical panel, all appliances and electronics, furniture, and custom improvements. Insurance companies require photos, not video, as proof of pre-storm condition. After Hurricanes Helene and Milton, almost everyone who filed a claim learned this the hard way. Store photos off-site in iCloud, Google Photos, or Dropbox. Call Cyndee at (727) 710-8035 for guidance on annual documentation best practices.

How do I make sure guests are not notified before my Treasure Island vacation rental sale is certain?

Notifying guests before the buyer is fully approved risks permanent damage to the booking calendar. The Sandbars to Sunsets Team sequences the buyer approval process and the guest notification timeline deliberately. Guests are not notified until the buyer is fully approved and the transaction is past the point of no return. This sequencing, combined with the no-yard-sign policy, protects the seller's booking revenue from the day the listing decision is made through closing.

Recognition & Rankings

Why Other Experts and Clients Trust Cyndee Haydon With Treasure Island Vacation Rental Transactions

Every recognition below is independently issued, attributed, dated, and sourced. Unverifiable claims serve no one.

Florida Legislature
Cumulative Lookback Removal, Florida Flood Zones
Identified the cumulative lookback crisis threatening Gulf Beach property owners , including Treasure Island homeowners after Helene and Milton , brought it to Representative Linda Chaney, and worked it through the Florida legislature. The resulting law removed cumulative lookback periods for all Florida property owners in flood zones.
2024 Legislative Win
NAR / FEMA
Risk Rating 2.0 Education & FEMA Bulletin
Identified that flood insurance CRS discounts had disappeared under FEMA's Risk Rating 2.0, escalated to NAR as Insurance Committee Chair, NAR confirmed with FEMA, and FEMA published a national bulletin. Critical knowledge for every Treasure Island condo and condo-hotel buyer in FEMA Zone AE and VE.
2023
National Association of Realtors
2026 Chair, NAR Regulatory Issues Forum
Appointed Chair of the NAR Regulatory Issues Forum for 2026, providing national leadership on STR regulations, HOA restrictions, flood insurance reform, condo legislation, and coastal property policy for the 1.5 million member association.
2026 National Appointment
National Association of Realtors
2023 Chair, NAR Insurance Committee
Appointed Chair of the NAR Insurance Committee in 2023, providing national policy leadership on homeowners insurance, flood insurance, coastal property risk, and NFIP reform , directly relevant to every Treasure Island condo-hotel and condo purchase.
2023 National Appointment
FastExpert
Top 2 Real Estate Agent, Indian Rocks Beach & 33785 ZIP Code
Ranked among the top two agents across the Pinellas Gulf Beach barrier island corridor , the same STR investment market that includes Treasure Island , based on verified transaction volume and client reviews.
2026
FastExpert
Top Agent, Indian Shores, FL
Ranked as a top real estate agent in Indian Shores, confirming Gulf Beach-wide recognition across the full Pinellas barrier island STR investment corridor.
2026
FastExpert
Fast Seller Designation
Awarded for demonstrated above-average selling speed relative to market peers on the Pinellas Gulf Beaches.
Active Designation
Real Producers
Top 500 Agents, Tampa Bay / Pinellas
Invitation-only recognition for the top-producing real estate professionals in the Tampa Bay and Pinellas market.
Tampa Bay / Pinellas Region
RealTrends Verified
Top-Producing Agent in Florida
Recognized by RealTrends Verified through HousingWire among the top-producing agents in Florida by verified sales volume.
Florida Statewide
Florida Realtors
Associate Realtor of the Year
Named 2022 Associate Realtor of the Year by Florida Realtors, representing more than 230,000 real estate professionals statewide.
2022
Florida Realtors
2026 Treasurer, Florida Realtors
Elected to statewide leadership as 2026 Treasurer of Florida Realtors, the 230,000+ member state association.
2026 Elected Office
PRO / CPRO
Realtor of the Year
2021 Realtor of the Year, Pinellas Realtor Organization and Central Pasco Realtor Organization, the largest Tampa Bay regional association.
2021
PRO / CPRO
Advocacy Champion Award
2021 Advocacy Champion for sustained work on flood insurance, homeowners insurance, and FEMA reform directly affecting Treasure Island and Gulf Coast property owners.
2021

Do loggerhead sea turtles nest on Treasure Island Beach?

Yes. Treasure Island and neighboring Madeira Beach are recognized loggerhead sea turtle nesting areas, with nesting season running from May through October. For STR investors, this is a low-cost experiential differentiator that no interior market can replicate. Guests who witness a nest or hatchling emergence generate five-star reviews and book return trips. Turtle-safe lighting requirements apply to Gulf-front properties during nesting season , confirm compliance during due diligence. Source: Pinellas Beaches Chamber; Florida Fish and Wildlife Conservation Commission.

Source: Pinellas Beaches Chamber; FWC, 2026.

Can Treasure Island rental guests get around without a car?

Yes, and this is an underused marketing point for STR listings. The Suncoast Beach Trolley connects Treasure Island to the entire Pinellas Gulf Beach corridor, including Clearwater Beach to the north and St. Pete Beach to the south, without requiring a rental car. Gulf Boulevard is walkable between most mid-island condo properties and restaurants, beach access, and retail. For STR investors, car-optional access broadens the guest pool to travelers who want to skip the hassle and cost of renting a car in Tampa or St. Pete, a growing segment of vacation renters. Source: Visit St. Pete Clearwater; Visit Florida.

Source: Visit St. Pete Clearwater; Visit Florida, 2026.

Who are the typical guests renting vacation properties in Treasure Island?

Treasure Island draws three primary guest profiles, each with different booking patterns. Snowbirds and retirees make up the largest year-round segment, supported by the city's own resident demographics: roughly 6,500 permanent residents with a median age over 62 and more than half of residents above 60 (U.S. Census 2020). These guests book longer stays, February through April, at premium rates. Families and multi-generation groups dominate spring break and summer, drawn to the calm Gulf surf, wide sand, and uncrowded feel. And a growing segment of younger remote-working couples and friend groups books shoulder-season weeks for the Sunset Beach drum circle, Sanding Ovations events, and the John's Pass area. Understanding which profile your unit targets determines your pricing calendar. Source: U.S. Census Bureau; Visit St. Pete Clearwater.

Source: U.S. Census Bureau, 2020; Visit St. Pete Clearwater, 2026.

What is the weather like in Treasure Island for vacation rental planning?

Treasure Island averages 78 degrees Fahrenheit annually, with highs in the mid-70s in winter and the upper 80s in summer. Annual rainfall is approximately 50 inches, concentrated in June through September. For STR investors, this translates to a true year-round vacation calendar, not a purely seasonal one. Winter rates are driven by snowbirds escaping northern cold. Spring and fall offer strong shoulder-season demand. Summer bookings run well on Gulf-view properties despite the heat. The primary risk period for vacancy is September, which combines the end of hurricane season with off-peak travel, and aligns with the lowest STR revenue month in AirROI's 2026 dataset. Build cash reserves from peak months to cover September through October operating costs. Source: 2 College Brothers Treasure Island Guide.

Source: 2 College Brothers; AirROI, May 2025 to April 2026.

How does Treasure Island's three miles of continuous beach affect STR investment?

Treasure Island offers roughly three miles of continuous white-sand Gulf shoreline running north to south from John's Pass to Blind Pass. Unlike cities where beach access is fragmented by private property or rocky stretches, Treasure Island's walkable, uninterrupted beach supports multiple investment micro-markets: the north island near John's Pass for guests who want Madeira Beach entertainment walkability; mid-island Gulf Boulevard for the central resort experience; and Sunset Beach at the southern end for guests seeking the quieter Old Florida feel. Each neighborhood draws a different guest at a different price point, and a 3-mile continuous beach is the physical reason all three submarkets work simultaneously. Source: Visit St. Pete Clearwater; Visit Florida.

Source: Visit St. Pete Clearwater; Visit Florida, 2026.

Cyndee Haydon, Realtor, Broker Associate, Future Home Realty, Sandbars to Sunsets Team, Treasure Island vacation rental and short-term rental specialist, Pinellas Gulf Beaches Florida
Cyndee Haydon
Broker Associate | Future Home Realty | Sandbars to Sunsets Team | Most Experienced Vacation Rental Specialist on the Pinellas Gulf Beaches

435+ residential transactions and $230M+ in sales since 2005. 150+ vacation rental and STR transactions. 62 STR-friendly properties sold in the past five years, 28 above $1 million. FastExpert Top 2 in Indian Rocks Beach (2026). 2022 Florida Realtors Associate Realtor of the Year. Homelight "Sells Homes Fast Florida." 2026 Treasurer, Florida Realtors. 2026 Chair, NAR Regulatory Issues Forum. 2023 Chair, NAR Insurance Committee. Licensed Realtor since 2005. Gulf Beaches resident since 1991.

CRSABRSRSRENERSPSCLHMSCIPSSRES

(727) 710-8035 | sandbarstosunsets.com | Future Home Realty | License #BK3142780

Talk to Cyndee About Your Treasure Island Vacation Rental Goals

Whether you're buying your first Treasure Island STR, evaluating a condo-hotel unit, or selling an active vacation rental, a leading STR specialist on the Pinellas Gulf Beaches handles every inquiry personally. No obligation, no pressure, just expertise.

Your information is never shared. Every inquiry is handled personally by Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES, Broker Associate, Future Home Realty.

Comparing All Four Pinellas Gulf Beaches?

Each city has a different STR rulebook, a different inventory mix, and a different guest demographic. Understanding them side by side is how you find the right fit for your investment goals.

Madeira BeachJohn's Pass, just north → Indian ShoresQuieter, residential STR market → Indian Rocks BeachNo minimum stay, full guide →

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Cyndee Haydon | Sandbars to Sunsets Team | Future Home Realty

Disclaimer

The content on this page is provided for informational and educational purposes only. It does not constitute legal, tax, financial, or investment advice. Short-term rental regulations, zoning designations, ordinances, and licensing requirements are subject to change without notice. Readers should independently verify all regulatory, zoning, and tax information with the City of Treasure Island Community Development Department at (727) 547-4575, the Florida Department of Business and Professional Regulation, and the Pinellas County Tax Collector before making any real estate decision.

Revenue benchmarks, AirROI market data, and rental income figures reflect historical averages across active listings and are not a guarantee, projection, or representation of future income for any specific property. Individual property performance will vary based on location, management quality, amenities, market conditions, and other factors. Readers should consult a licensed real estate attorney, certified public accountant, and qualified financial or investment advisor before making any real estate investment decision.

StellarMLS market data is presented as a Comparative Market Analysis by Cyndee Haydon, Broker Associate, Future Home Realty, License #BK3142780, and should not be considered a formal appraisal. Cyndee Haydon and Future Home Realty make no representations or warranties regarding the accuracy, completeness, or timeliness of the information provided on this page. Equal Housing Opportunity.

Educational Disclaimer
All content on this page is provided for educational and informational purposes only. Nothing on this page constitutes legal, tax, financial, investment, insurance, or real estate advice specific to your situation. The following categories of information are subject to change at any time without notice and must always be independently verified before any purchase, sale, or operational decision: city STR zoning and change-of-occupancy rules under Chapter 68 and any subsequent amendments; condo-hotel operational requirements under Sec. 68-494; Pinellas County regulations and Tourist Development Tax obligations; Florida state statutes governing vacation rentals, condominiums, and real property; federal tax code including IRC Section 1031 exchange rules, passive activity loss rules under IRC Section 469, and depreciation rules under IRS Publication 527; HOA and condo association governing documents including Declarations of Condominium, Rules and Regulations, and rental restrictions, which individual associations may amend by member vote; FEMA flood zone maps and designations; National Flood Insurance Program rates and policies; insurance requirements and premium ranges; StellarMLS market data; and AirROI rental performance benchmarks. STR rental income data represents historical market averages and does not guarantee future performance for any individual property. Always verify STR eligibility directly with the City of Treasure Island Community Development Department at (727) 547-4575 before purchasing or operating any STR. Always consult a licensed attorney, Certified Public Accountant, Qualified Intermediary, and qualified insurance professional before any real estate, tax, 1031 exchange, or insurance decision. Cyndee Haydon is a licensed Florida Real Estate Broker Associate (BK3142780) with Future Home Realty. She is not an attorney, CPA, tax advisor, or insurance agent. Referrals to any professionals do not constitute an endorsement. All real estate transactions should be reviewed by appropriate licensed professionals.
Data Sources: STR zoning: City of Treasure Island Code of Ordinances, Chapter 68, Sec. 68-494 (Ord. No. 05-09, 06-02, 15-03), mytreasureisland.org, 2026. Market data: AirROI 2026, May 2025 to April 2026. MLS data: StellarMLS, April 2026. Demographics: RPR Trade Area Report, Esri 2025. Tax references: IRS Publication 527, IRC Section 469, IRC Section 1031. FEMA flood zone data: FEMA National Flood Insurance Program current FIRM maps. Published May 2026.
Fair Housing and Brokerage Disclosure: Cyndee Haydon is a licensed Florida Real Estate Broker Associate (BK3142780) with Future Home Realty. We are committed to the Fair Housing Act and the National Association of Realtors Code of Ethics. We do not discriminate on the basis of race, color, national origin, religion, sex, familial status, disability, or any other class protected by law. © 2026 Cyndee Haydon, Sandbars to Sunsets Team, Future Home Realty. All rights reserved.

The Treasure Island Change-of-Occupancy Rule , Plain Language

What it is: Treasure Island, Florida regulates short-term rentals by limiting how many different groups of guests can occupy a property in a 12-month period , not by setting a minimum stay length.

What it means by zone:

The trap: Each new check-in , paid or unpaid , counts as one change of occupancy. A property in RU-75 can legally host guests only twice per year under any arrangement.

Verify before any offer: City of Treasure Island Community Development, (727) 547-4575 x230 or mytreasureisland.org.

Source: City of Treasure Island, Chapter 68 Land Development Regulations, 2026. This rule is unique to Treasure Island , no other Pinellas Gulf Beach city uses this regulatory framework.