The most complete resource on Madeira Beach vacation rental rules, zoning, market data, and investment strategy on the Gulf Coast. Written by a Madeira Beach resident and waterfront property owner since 2018. Zoning determines everything here. Read this before you write an offer.
Madeira Beach, known locally as "Mad Beach," is a 2.5-mile barrier island city in Pinellas County, Florida, sitting between Redington Beach to the north and Treasure Island to the south. The ZIP code is 33708. The nickname is a catchy portmanteau of the full city name, deeply embedded in local culture and adopted by businesses from Mad Beach Surf Shop to Mad Beach Brewing on the Intracoastal Waterway. The official city slogan, "Two miles long and a smile wide," appears on city seals, welcome signs, and tourist apparel at John's Pass, and captures exactly what the place feels like: compact, coastal, and genuinely welcoming.
Unlike most of its neighbors, Madeira Beach regulates short-term rentals entirely through zoning, not a single citywide ordinance. Whether you can rent for a week or must rent for six months depends entirely on where the property sits on the city's official restriction map.
That map, combined with John's Pass Village (Pinellas County's number one tourist destination), a deep condo inventory dating back to the 1950s through 1980s construction boom, and strong post-2024 hurricane recovery demand, makes Madeira Beach one of the most opportunity-rich and most misunderstood STR markets on the Gulf Coast.
The three things that set Madeira Beach apart from every other Pinellas Gulf Beach city: a published, publicly available zoning restriction map that determines STR eligibility parcel by parcel; John's Pass Village, a walkable boardwalk attraction with no peer on the Gulf Coast; and an active STR condo market with 731 active Airbnb listings and 25.8% year-over-year revenue growth as of May 2026.
"Madeira Beach is the most complex STR market on the Pinellas Gulf Beaches, and I say that as someone who has lived here since 2018 and owns waterfront property here. The restriction map is public, the rules are knowable, and the investors who do the homework before they write an offer are the ones who find the deals that others miss. I walk these streets, I know these buildings, and I know which ones deserve a closer look and which ones come with questions you need answered before you fall in love with the listing."
Madeira Beach is the only Pinellas Gulf Beach city with a published, color-coded Vacation Rental Restriction Map that identifies permissible rental periods lot by lot. This is the most important document for any investor. Here is how to read it and what each zone means for your investment strategy.
Properties currently listed and actively renting on Airbnb or VRBO in restricted zones may be operating illegally or under unverifiable grandfather claims. Do not assume a live listing means legal operation. Verify the zoning designation in writing with the Madeira Beach Planning Department before you close. The city's enforcement path leads to the Special Master, fines of $250 per day, and property liens that travel with the deed.
The current STR framework is Ordinance No. 2018-01, adopted September 11, 2018, and codified as Section 110-843 of the Madeira Beach Code of Ordinances. That ordinance defines a short-term rental as any rental period of less than 30 consecutive days. The City of Madeira Beach publishes its official Vacation Rental Restriction Map at madeirabeachfl.gov (published August 24, 2021) showing which parcels are zoned for STR, 90-day, or 6-month minimums. For zoning verification on a specific parcel, contact the Madeira Beach Community Development Department at (727) 391-9951.
| Zone | Name | STR Status | City Minimum Stay | Best Investment Use |
|---|---|---|---|---|
| R-1 | Single-Family Residential | Prohibited | 6 months or longer | Annual lease, primary home, second home |
| R-2 | Low Density Multifamily | Prohibited | 90 days or longer | Snowbird seasonal lease (90+ days) |
| R-3 | Medium Density Multifamily | Allowed | None (HOA rules apply) | Vacation rental, Airbnb, weekly STR |
| C-1 | John's Pass Village Activity Center | Allowed | None (Ordinance 2024-09 applies) | High-walkability STR, mixed-use investment |
| C-3 | Retail Commercial | Allowed | None (above first-floor commercial) | STR above ground-floor retail or office |
| C-4 | Marine Commercial | Allowed | None (above first-floor commercial) | Marina-adjacent STR, working waterfront |
Source: Madeira Beach Code of Ordinances, Sections 110-176 (R-1), 110-201 (R-2), and Chapter 110 (R-3, C-1, C-3, C-4); Ordinance No. 2018-01 (September 11, 2018, Section 110-843); Ordinance 2024-09. Verify current zoning with the Madeira Beach Community Development Department at (727) 391-9951 before purchase.
Under Ordinance No. 2018-01 (adopted September 11, 2018, codified as Section 110-843), Madeira Beach defines a short-term vacation rental as any rental period of less than 30 consecutive days. This is the city's baseline definition. Whether a property can legally operate as an STR depends on its zoning district.
The zoning code adds district-specific minimum-stay requirements: Section 110-176 (R-1 Single-Family) treats any rental shorter than six months as a prohibited short-term rental; Section 110-201 (R-2 Low Density Multifamily) treats any rental shorter than three months as a prohibited short-term rental. Properties in R-3, C-1, C-3, and C-4 zones may operate vacation rentals with no city minimum-stay requirement.
At the state level, Florida Statute 509.242 defines a vacation rental as a unit rented more than three times per year for periods shorter than 30 days or one calendar month, whichever is less.
Madeira Beach has one of the longest and most legally significant STR regulatory histories on the Pinellas Gulf Beaches. Understanding this timeline explains why the current rules exist, why they are legally permanent under Florida law, and why due diligence here is non-negotiable.
| When | What Happened | What Changed | Investor Implication |
|---|---|---|---|
| Pre-2006 | No formal STR ordinance | Short-term rentals operated broadly across the city with no zoning restrictions or registration requirements | Some owners from this era claim grandfather status. Document requirements are strict |
| 2006 | City bans STR in residential zones | Madeira Beach enacts its first ordinance prohibiting short-term rentals in R-1 and R-2 residential neighborhoods to protect neighborhood character. This is the origin of the current six-month minimum in R-1 (Code Section 110-176) and three-month minimum in R-2 (Code Section 110-201) | Properties operating STR in restricted zones after 2006 without verified grandfather documentation were doing so illegally from that date forward |
| June 1, 2011 | Florida passes FS 509.032(7)(b) | Florida law prohibits any new local ordinance from banning vacation rentals or regulating their duration or frequency. Critically, the law expressly exempts all ordinances adopted on or before June 1, 2011. Madeira Beach's 2006 residential restrictions predate this cutoff and are therefore permanently grandfathered under state law | This is why Madeira Beach's R-1 and R-2 restrictions cannot be overridden by state preemption and are legally permanent. No future Florida legislature action changes this. Plan your investment around these rules as fixed |
| 2015–2016 | City enforcement wave | City identifies 100+ properties suspected of violating the residential STR prohibition. Cases proceed to the Special Master. Every case brought results in a finding of violation. Fines of $250 per day plus legal fees exceeding $1,000 per case. Unpaid fines become property liens (Tampa Bay Times, April 28, 2016) | The city will enforce. Active Airbnb listings are treated as primary evidence of violation. No complaint from a neighbor is required to trigger investigation |
| Sept. 11, 2018 | Ordinance No. 2018-01 adopted | The current controlling STR standards ordinance, codified as Section 110-843. Defines STR as any rental of less than 30 consecutive days. Establishes compliance requirements including the Local Business Tax Receipt, annual renewal, posted registration, and safety code compliance (Residential Swimming Pool Safety Act, Florida Building Code, Florida Fire Prevention Code) | All current STR compliance questions in Madeira Beach trace to this ordinance. Source: Pinellas Realtor Organization; Madeira Beach Code Section 110-843 |
| Aug. 24, 2021 | Vacation Rental Restriction Map published | City publishes the official color-coded parcel map at madeirabeachfl.gov formalizing zoning-based rules: green (STR allowed), blue (90-day minimum R-2), red (6-month minimum R-1) | The map is your first due diligence tool. Green does not mean the HOA allows it. Verify both city zoning and HOA policy before purchase |
| 2024 | Ordinance 2024-09 adopted | Replaces C-1 Tourist Commercial with the John's Pass Village Activity Center, creating six character districts (Boardwalk, Commercial Core, John's Pass Resort, Low Intensity Mixed Use, Traditional Village, Transitional). Vacation rental is a permitted use in multiple character districts | C-1 investments now require character district verification under Ordinance 2024-09 in addition to base zoning confirmation |
Sources: Madeira Beach Code of Ordinances, Sections 110-843, 110-176, and 110-201; Ordinance No. 2018-01 (September 11, 2018); Florida Statute 509.032(7)(b); Ordinance 2024-09; Vacation Rental Restriction Map (August 24, 2021, madeirabeachfl.gov); Tampa Bay Times, April 28, 2016; Pinellas Realtor Organization (pinellasrealtor.org).
In 2006, Madeira Beach prohibited short-term rentals in R-1 and R-2 zones. A grandfather exemption applies only to properties that can document all four of the following: (1) the property was used as a vacation rental before the 2006 ordinance; (2) vacation rental use has been continuous since that date with no gaps; (3) the owner holds a current city Business Tax Receipt for the rental; and (4) sales tax has been paid on all rental income throughout the period.
If a seller claims grandfather status in a red or blue zone, require documentation of all four elements as a condition of your due diligence. A verbal claim and an active Airbnb listing are not documentation. If the seller cannot produce it, assume the grandfathering does not exist. Grandfathered status may not transfer automatically on sale. Confirm with the Madeira Beach Community Development Department, (727) 391-9951, in writing before closing.
In 2024, Madeira Beach replaced the old C-1 Tourist Commercial District with the John's Pass Village Activity Center under Ordinance 2024-09. The Activity Center establishes six character districts within the John's Pass area: the Boardwalk, Commercial Core, John's Pass Resort, Low Intensity Mixed Use, Traditional Village, and Transitional.
In the Commercial Core and John's Pass Resort districts, residential uses and vacation rentals are allowed above first-floor commercial space. The John's Pass Resort district also allows temporary lodging and resort-style operations on the east side of Gulf Boulevard. For an investor, properties in the C-1 zone have the highest walkability premium on the Pinellas Gulf Beaches and may qualify for resort-density vacation rental use, subject to the specific character district designation. Verify the character district for any C-1 parcel before purchase.
Under the Pinellas County Certificate of Use program, the city baseline is two guests per bedroom plus up to two additional guests in a common area, with a total maximum of ten guests. All occupants of all ages count regardless of whether they sleep in a bedroom.
Critical rule: the HOA or condo association's occupancy limit overrides the city's limit whenever the association's rule is more restrictive. Many Madeira Beach condo buildings cap occupancy at six guests regardless of bedroom count. Some buildings cap it lower. The association's Declaration of Condominium and current Rules and Regulations are the controlling documents, not the city ordinance. If the county says ten guests are permitted but your HOA says six, the answer is six.
The same principle applies to all other STR rules at the building level: HOA minimum-stay requirements, noise curfews, pool hours, parking rules, and guest registration policies set by the association override city minimums whenever they are more restrictive. Florida law (Chapter 718 for condominiums, Chapter 720 for homeowners associations) gives associations broad authority to regulate use of units beyond what the city requires. Always read the full declaration and current board-adopted rules before you host a single guest.
Based on Madeira Beach's 2015 to 2016 enforcement wave, which targeted properties violating the residential STR prohibition first established in 2006 (Tampa Bay Times, April 28, 2016): code enforcement officers document violations, including online platform listings as evidence. A citation is issued with the right to a Special Master hearing. If found in violation, fines run $250 per day until corrected. Legal fees frequently add $1,000 or more per case. Unpaid fines become property liens that must be cleared before sale.
In every Special Master case the city brought during that enforcement wave, the property was found in violation. The current framework under Ordinance No. 2018-01 (Section 110-843) strengthened registration requirements and safety standards. Contact the Madeira Beach Community Development Department at (727) 391-9951 with compliance questions.
Apply at Madeira Beach City Hall, 300 Municipal Drive. Renews annually. Must be posted visibly at the rental property. Formerly called an occupational license.
Issued by the Florida Department of Business and Professional Regulation (DBPR). Required for all vacation rentals operating under Florida Statute 509.242. Apply at myfloridalicense.com. DBPR: (850) 487-1395.
Register with the Pinellas County Tax Collector for Tourist Development Tax collection and remittance. TDT: (727) 464-5007. Monthly filing required even in zero-revenue months.
Register at floridarevenue.com for your Dealer Number. Required for state sales tax compliance. Platforms like Airbnb and VRBO collect and remit state sales tax for their bookings automatically.
Required under the Pinellas County STR program. Covers safety inspections, occupancy caps, and parking standards. Apply at pinellas.gov/str.
Airbnb and VRBO automatically collect and remit all three taxes for bookings made through their platforms. For direct bookings, the owner is responsible for collecting and remitting the full 13% to the appropriate agencies. TDT is due by the 20th of the following month. Late penalty: 10% of tax due or $50 minimum, plus interest.
What is taxable: nightly rates, cleaning fees, pet fees, damage insurance fees, and all other mandatory charges. Keep all records for at least three years.
Collection allowance: Owners who file and pay TDT electronically and on time may deduct 2.5% of the tax collected as a collection allowance, up to $30 per filing period. File on time to qualify.
The Haydon SHORE™ STR Investment Framework is Cyndee Haydon's proprietary five-factor evaluation system for vacation rental properties. Every Madeira Beach STR purchase should be underwritten through all five factors before you commit.
731 active Airbnb listings as of May 2026. Supply grew 26.5% in the past year, yet revenue grew 25.8%, meaning demand is absorbing new supply rather than being diluted by it. The median condo sold for $725,000 in April 2026 at 95% of list price and 55 days on market, reflecting stable but not feverish demand.
88.1% of listings are condos. 2-bedroom units dominate at 49.5%. The condo market is deep and competitive. Single-family STR homes are rare and command a premium when in R-3 or commercial zones.
Zoning controls everything. Confirm the parcel is green (R-3 or commercial) on the city's Vacation Rental Restriction Map before you negotiate. Then verify the condo HOA's minimum-stay policy, which is often stricter than the city's. Many buildings require 7-day minimums even in R-3 zones.
HOA rules override city rules when they are more restrictive. This applies to minimum stays, occupancy limits, parking, pool hours, and noise. The association's Declaration and board-adopted rules are the controlling documents. Register with the city (Business Tax Receipt), DBPR (state vacation rental license), Pinellas County Tax Collector (TDT), and Florida Department of Revenue before hosting.
Underwrite to the median, not the average. Median monthly revenue is $3,659. At a $725,000 purchase price with 25% down ($181,250) at a 6.5% rate, your principal and interest is approximately $3,490/month before taxes, insurance, HOA, management, and vacancies.
Budget: 13% tax on gross revenue. STR-specific insurance ($5,000 to $15,000/year range on the Gulf Coast). Property management if self-managing is not realistic (10-20% of revenue). HOA fees ($500 to $1,500/month depending on building). Clean reserves for September and October.
The entire city of Madeira Beach sits in FEMA-mapped Special Flood Hazard Areas. Most parcels are Zone AE or Zone VE. Hurricane Helene (September 26, 2024) and Hurricane Milton (October 9, 2024) struck 13 days apart. Ground-floor units and single-story homes flooded. Many properties triggered FEMA's 50% Rule, requiring full elevation before rebuilding.
On any purchase, ask: Did this property flood in Helene or Milton? What permits were pulled for repairs? Does cumulative improvement work approach the 50% threshold? Reviewing the building's master insurance policy and the seller's CLUE report early in the process, and having a conversation with an insurance agent who specializes in Florida coastal STR condos before you finalize your offer, puts you in a much better position than learning about coverage gaps after closing.
Top 10% of Madeira Beach listings earn $9,244 or more per month. Top 25% earn $6,265 or more. These are not guaranteed. They require proximity to John's Pass for the walkability premium, family amenities (changing tables and baby gear add 225% to 287% revenue uplift per AirROI data), professional photography (40-plus photos is market standard), and a local management team.
Verify rental history from a verified source before you buy. Project from the AirROI median, aim for the top quartile, and build in three months of low-season reserves. March is peak. September is lowest.
The following data covers the 12-month period May 2025 through April 2026. Source: AirROI, May 2026. All figures are market averages across 731 active Airbnb listings in Madeira Beach. Well-managed, well-positioned listings consistently outperform these averages.
Do not underwrite to the average. Underwrite to the median and build a management and amenity plan to reach the top quartile. The gap between a median listing and a top-25% listing represents more than $30,000 in annual revenue at Madeira Beach.
| Performance Tier | Monthly Revenue | Occupancy | ADR | RevPAR | Annual Revenue Est. |
|---|---|---|---|---|---|
| Best-in-Class (Top 10%) | $9,244+ | 82%+ | $454+ | $244+ | $110,900+ |
| Strong Performers (Top 25%) | $6,265+ | 64%+ | $337+ | $160+ | $75,180+ |
| Typical (Median) | $3,659 | 43% | $261 | $101 | $43,908 |
| Entry-Level (Bottom 25%) | $1,942 | 23% | $200 | $62 | $23,300 |
Source: AirROI, Madeira Beach Airbnb Market Data 2026, May 2025 to April 2026. Annual revenue estimates are monthly figures times 12; actual results vary by month, amenities, management quality, and listing position.
Source: AirROI, Madeira Beach seasonality data, May 2025 to April 2026. Build a three-month cash reserve for August through October before closing.
"The seasonality in Madeira Beach is real, and buyers who do not budget for it run into trouble around month nine. March can feel like everything is working beautifully. September will test whether the numbers actually pencil. The investors I work with who sleep well in October are the ones who modeled both months before they wrote their offer."
The data below reflects only condos and properties eligible for short-term rentals of one month or less in Madeira Beach, filtered from StellarMLS. This is not the entire Madeira Beach condo market. It is the specific inventory available to STR investors.
Source: StellarMLS data for STR-eligible properties in Madeira Beach, FL. Data pulled May 17, 2026. Cyndee Haydon, Future Home Realty. This is a Comparative Market Analysis and not a formal appraisal.
What the 95% sold-to-list ratio tells you: Sellers are receiving close to asking price, which means negotiating room is limited. Buyers who want to buy below ask need to identify days-on-market outliers (CDOM 100+), price-reduced listings, or properties with known deferred maintenance or flood history. There were active listings in this dataset with CDOM over 400 days, primarily in the Madeira Beach Yacht Club complex and Surfside South, suggesting price sensitivity at certain price points within those buildings.
The following 42 buildings represent MLS-verified STR-eligible properties in Madeira Beach, filtered to allow rentals of one month or less. All 42 building names are confirmed. Sold prices are from verified StellarMLS closed transactions within the past 1,000 days. This is the most complete publicly available list of STR-eligible condo buildings in Madeira Beach.
City zoning allows STRs in these buildings, but many HOA declarations impose minimum stay requirements of 7 days, 14 days, or 30 days that are stricter than the city's rules. Florida condo law (Chapter 718) means building rental restrictions can be amended by a supermajority vote. Get the current declaration, bylaws, and any board-approved rental policies in writing during your 7-business-day inspection period under Florida's 2025 condo disclosure law.
Condo-Hotel properties are designated separately in this table. Many conventional mortgage lenders will not finance a condo-hotel purchase. These properties typically require a portfolio loan, commercial financing, or a non-warrantable condo lender. Confirm lender eligibility before writing an offer on any condo-hotel unit.
| Building / Complex | Address | Type | Yr Built | Sold Price (1,000-day MLS) | Sqft (sold unit) | Waterfront | HOA Min Stay |
|---|---|---|---|---|---|---|---|
| Gulf Lane — South End (John's Pass Area) | |||||||
| Beach Place Condominiums | 12901 Gulf Ln | Condo | — | $647,000 (Mar 2025) | 1,140 | Yes | Verify w/ HOA |
| Crimson on the Gulf Condo | 12935 Gulf Ln | Condo | 1994 | $825,000 (Apr 2026) | 1,205 | Yes | Verify w/ HOA |
| Madeira Norte Condos | 13000 Gulf Ln | Condo | — | $900,000 (Jan 2024) | 940 | Yes | Verify w/ HOA |
| Princess Condominiums | 13398 Gulf Ln | Condo | — | $1,555,000 (Feb 2024) | 2,050 | Yes | Verify w/ HOA |
| Gulf Blvd — South (12xxx–13xxx) | |||||||
| Sandy Shores Condo | 12924 Gulf Blvd | Condo | 1979 | $675,000 (Nov 2023) | 1,005 | Yes | Verify w/ HOA |
| Madeira Bay Resort I | 13101 Gulf Blvd | Condo-Hotel | 2020 | $595,000 (Oct 2025) | 762 | Yes | Hotel program |
| Madeira Bay Resort II | 13235 Gulf Blvd | Condo-Hotel | 2006 | $500,000 (Oct 2025) | 734 | Yes | Hotel program |
| Chambre The Condo | 13336 Gulf Blvd | Condo | 1988 | $530,000 (Apr 2026) | 850 | Yes | Verify w/ HOA |
| Wave Resort Condo | 13343 Gulf Blvd | Condo | 1950 | $195,000 (Jul 2024) | 240 (small studio) | No | Verify w/ HOA |
| Collwood The Condo | 13440 Gulf Blvd | Condo | 1981 | $940,000 (Mar 2024) | 1,055 | Yes | Verify w/ HOA |
| Sea Breeze of Madeira Condo | 13500 Gulf Blvd | Condo | 1982 | $887,500 (Dec 2024) | 1,420 | Yes | Verify w/ HOA |
| Bellarte on the Gulf | 13630 Gulf Blvd | Condo | 2007 | $3,050,000 (Mar 2026) | 3,186 | Yes | Verify w/ HOA |
| Madeira Sands Condo | 13650 Gulf Blvd | Condo | 1980 | $1,150,000 (Aug 2024) | 1,455 | Yes | Verify w/ HOA |
| Villa Madeira Condo | 13720 Gulf Blvd | Condo | 1981 | $1,050,000 (May 2024) | 1,160 | Yes | Verify w/ HOA |
| Skyline of Madeira | 13999 Gulf Blvd | Condo-Hotel | — | $600,000 (Jul 2024) | 877 | Yes | Hotel program |
| Gulf Blvd — Central (14xxx) | |||||||
| Madeira Place Condo | 14001 Gulf Blvd | Condo | 1981 | $339,500 (Feb 2025) | 840 | No | Verify w/ HOA |
| Beach Club of Madeira | 14010 Gulf Blvd | Condo | — | $3,000,000 (Dec 2023) | 3,037 | Yes | Verify w/ HOA |
| Arena De Madeira Condominiums | 14110 Gulf Blvd | Condo | — | $998,000 (Dec 2023) | 1,355 | Yes | Verify w/ HOA |
| Gulf Gardens Motel Apts Condo (boutique, ~18–20 units; bungalows and studios) | 14141 Gulf Blvd | Condo | — | $310,000 (Dec 2023) | 455 (studio) | No | Verify w/ HOA |
| Trillium Condo | 14146 Gulf Blvd | Condo | 1981 | $785,000 (Apr 2026) | 1,165 | Yes | Verify w/ HOA |
| Tropic Shores Apt Motel Condo | 14251 Gulf Blvd | Condo-Hotel | 1958 | $300,000 (Nov 2024) | 393 | No | Hotel program |
| Kima Condominiums | 14300 Gulf Blvd | Condo | — | $795,000 (Jan 2026) | 1,120 | Yes | Verify w/ HOA |
| La Coquina Condominiums | 14401 Gulf Blvd | Condo | — | $600,000 (Mar 2025) | 1,150 | No | Verify w/ HOA |
| Arie Dam Condo | 14600 Gulf Blvd | Condo | 1984 | $880,000 (May 2026) | 1,070 | Yes | Verify w/ HOA |
| The Seaview Condominiums | 14700 Gulf Blvd | Condo-Hotel | — | $1,050,000 (May 2024) | 1,405 | No | Hotel program |
| Las Brisas of Madeira Condo | 14710 Gulf Blvd | Condo | 1981 | $1,050,000 (May 2025) | 1,440 | No | Verify w/ HOA |
| Madeira Vista Condominiums | 14800 Gulf Blvd | Condo | — | $635,000 (May 2024) | 1,210 | No | Verify w/ HOA |
| Gulf Blvd — North (14900–15462) | |||||||
| Surfside South Condo | 14900 Gulf Blvd | Condo | 1980 | $811,000 (May 2024) | 1,100 | Yes | Verify w/ HOA |
| Ocean Sands One Condo | 14950 Gulf Blvd | Condo | 1980 | $740,000 (Sep 2024) | 1,225 | Yes | Verify w/ HOA |
| Ocean Sands Two Condo | 15000 Gulf Blvd | Condo | 1981 | No closed sales in 1,000-day window | — | — | Verify w/ HOA |
| Gulf Shores 2nd Add (new construction) | 14048 Gulf Blvd | Condo | 2024–2026 | $2,799,000 (May 2026) | 2,330 | Yes | Verify w/ HOA |
| Madeira Towers Condo | 15316 Gulf Blvd | Condo | 1978 | $755,000 (Jan 2025) | 1,265 | Yes | Verify w/ HOA |
| Shores of Madeira Condo | 15400 Gulf Blvd | Condo | 1977 | $790,000 (Sep 2025) | 1,190 | Yes | Verify w/ HOA |
| Surfside Tower Condo | 15462 Gulf Blvd | Condo | 1978 | $1,275,000 (Sep 2023) | 1,100 | Yes | Verify w/ HOA |
| 150th Ave / Town Center Area | |||||||
| Harbor at Town Center | 300 150th Ave | Condo | 2020–2022 | $660,000 (May 2025) | 1,390 | Yes | Verify w/ HOA |
| Madeira Cove Condo | 399 150th Ave | Condo | 1997–1999 | $600,000 (Jan 2024) | 1,250 | Yes | Verify w/ HOA |
| The Residences at Town Center | 400 150th Ave | Condo | 2024 | $1,000,000–$1,238,525 (2024–2026) | 1,852–2,067 | No | Verify w/ HOA |
| Boca Vista Condominium | 401 150th Ave | Condo | 1983 | $577,000 (May 2024) | 1,290 | Yes | Verify w/ HOA |
| Snug Harbour Condo | 423 150th Ave | Condo | 2003 | $949,000 (Oct 2023) | 1,825 | Yes | Verify w/ HOA |
| Aljean Shores Condo | 54 154th Ave | Condo | — | $479,000 (Oct 2023) | 720 | No | Verify w/ HOA |
| Other STR-Eligible Addresses | |||||||
| Madeira Del Mar Condo | 15305 1st St E | Condo | 2021 | $942,500 (Mar 2024) | 1,800 | No | Verify w/ HOA |
| Madeira Beach Yacht Club | 165 Medallion Blvd (bay-side) | Condo | 1973 | $345,000 (May 2026) | 430 | No | 7 days (verify) |
All 42 STR-eligible buildings are confirmed by name. This is the most complete publicly available list of STR-eligible condo communities in Madeira Beach, verified against StellarMLS sold transaction data for the past 1,000 days.
Madeira Bay Resort I (13101), Madeira Bay Resort II (13235), Skyline of Madeira (13999), Tropic Shores (14251), and The Seaview (14700) are designated Condo-Hotel in StellarMLS. Conventional mortgage financing is typically not available.
$195,000 (240 sqft studio, Wave Resort) to $3,050,000 (3,186 sqft waterfront penthouse, 13630 Gulf Blvd). Median sold transaction among known sales: approximately $800,000.
Source: StellarMLS closed transaction data, STR-eligible properties in Madeira Beach, FL allowing rentals of one month or less. Data verified May 2026. 1,000-day sold window. Cyndee Haydon, Future Home Realty. This is a Comparative Market Analysis and not a formal appraisal. HOA minimum-stay policies are independently set and subject to change. Verify with the association during your inspection period. Building names marked (*) require independent MLS verification.
No other Pinellas Gulf Beach city has a walkable attraction ecosystem like John's Pass Village and Boardwalk. For STR investors, that proximity is a measurable revenue and booking-rate premium, not a subjective nice-to-have.
John's Pass was carved on September 27, 1848, by a massive unnamed hurricane known as the Great Gale of 1848, which cut through the barrier islands and permanently separated Madeira Beach to the north from Treasure Island to the south. The pass was named after John LeVique, a French sailor and turtle fisherman who was among the first to navigate the newly formed inlet after returning from a trading trip to New Orleans.
Three more dates investors and guests need to know: In 1927, the first fixed bridge was built across John's Pass, connecting the two barrier islands and opening the area to development. In 1971, the original bridge was replaced by a more stable drawbridge structure, which remains today. The present-day John's Pass Village and Boardwalk features an 1,100-foot boardwalk, over 100 waterfront shops and restaurants, and serves as the primary departure point for deep-sea fishing, dolphin tours, and watersports.
For STR investors, two underappreciated facts about John's Pass: First, it is the only boat access to the Gulf of Mexico between Clearwater Beach and St. Pete Beach. Any boater coming south from Clearwater or north from St. Pete who wants to reach open Gulf waters must pass through John's Pass. That makes Madeira Beach the fishing charter hub of the Pinellas Gulf Beaches, home to deep-sea grouper charters and the reason the area is nicknamed "Grouper Capital of the World." Fishing tournaments, charter bookings, and the annual John's Pass Seafood Festival are all anchored to this geographic reality. Second, John's Pass sits within the feeding and breeding territory of one of the largest resident bottlenose dolphin populations in the Tampa Bay area. Pods are spotted daily from the John's Pass boardwalk, from shore near Eleanor Island, and from the beach itself. This is a significant guest experience driver that supports year-round bookings and 5-star reviews.
The Village that grew around John's Pass is now Pinellas County's number one tourist destination, with over 100 merchants, restaurants serving seafood since 1978 (The Friendly Fisherman), dolphin watching tours, charter fishing, pontoon and jet ski rentals, parasailing, and sunset cruises.
For a short-term rental within walking distance of John's Pass, the guest experience improvement is significant. Guests who can park the car and walk to dinner, the dolphin boat, the beach, and the boardwalk stay longer, leave better reviews, and rebook at higher rates. Listings that accurately describe this proximity outperform listings with comparable amenities in less walkable locations.
From a property within 0.5 mile of John's Pass Village, guests can walk to dining (20-plus restaurants), boardwalk shopping (100-plus merchants), dolphin watching and charter fishing, boat and jet ski rentals, parasailing, beach access, sunset cruises, the Royal Conquest Pirate Ship family cruise, and The Candy Kitchen, a Madeira Beach institution since 1950. No other Pinellas Gulf Beach city offers this density of walkable guest experiences from a single STR location.
At the northern end of Madeira Beach, Archibald Beach Park (15100 Gulf Blvd) offers metered public parking, restrooms, showers, a fishing pier, and picnic tables directly on the Gulf. Properties in the northern STR corridor, including Surfside Tower, Shores of Madeira, and Madeira Towers, have this park as a walkable guest amenity — relevant to guests who prioritize a quieter beach experience away from the John's Pass activity.
Dolphins daily, year-round. Madeira Beach is home to one of the largest resident bottlenose dolphin populations in the Tampa Bay area. Pods feed and play in the pass and along the shore daily. Guests can spot them from the boardwalk, from Eleanor Island, and directly from the beach. This is a genuine guest experience differentiator that generates 5-star reviews, repeat bookings, and referrals, particularly for family travelers and first-time Gulf Coast visitors.
Fishing charters and the Grouper Capital angle. Because John's Pass is the only Gulf water access between Clearwater Beach and St. Pete Beach, every fishing charter heading to open water from this stretch of the Gulf Beaches passes through here. The area is nicknamed the "Grouper Capital of the World" and hosts the largest annual seafood festival in Pinellas County. Guests who book at Mad Beach specifically for fishing access, boating, or the seafood festival are a distinct demand segment that adds bookings independent of pure beach-day weather. Year-round grouper fishing charters, near-shore trips, and back-bay tours all depart from the John's Pass marina.
Madeira Beach has one of the most event-dense calendars of any Pinellas Gulf Beach city. These events matter for STR investors because they generate bookings during months that would otherwise be softer, particularly November and December when the seasonality data shows a dip.
A three-day October event that is the largest annual STR demand spike in Madeira Beach. Hundreds of vendors, art and crafts, live music, and family activities. Typically Friday noon to 9 PM, Saturday 10 AM to 9 PM, Sunday 10 AM to 5 PM. Properties within walking distance of John's Pass command their highest weekend rates of Q4 during this event.
Started in 1996 by American Legion Post 273 in Madeira Beach, the Veterans Boat Parade runs on the Saturday closest to Veterans Day and is now in its 28th year in 2026. Boats are decorated with patriotic themes and parade through the Madeira Beach waterways past the shores of Madeira Beach, Redington Beach, and North Redington Beach. The event raises funds for veteran charities including Dogs Inc. and the USA Patriots Amputee Softball Team. For STR investors, this is a proven November booking driver, one of the harder months to fill. Source: veteransboatparade.org
The Madeira Beach Festival of Lights Holiday Boat Parade celebrates its 60th year in 2026 on Sunday, December 13, 2026. The parade begins at 6:30 PM and concludes between 9:45 and 10:00 PM as it reaches John's Pass. Decorated boats parade through Boca Ciega Bay with the finale at the John's Pass Boardwalk. This event, held each December, is a dependable December demand driver for STR units with bay views or close proximity to the waterway route.
R.O.C. Park (Recreation, Open Space and Community) is Madeira Beach's free public recreation park and hosts youth and adult baseball and softball tournaments throughout the year, including NSA events, King of the Beach Fishing Tournament, and Spring Break Rotary Carnival. The Madeira Beach Yacht Club condos sit within easy distance of R.O.C. Park, and tournament weekends consistently drive bookings for Yacht Club units in months that would otherwise see soft demand. Teams traveling to R.O.C. Park fill these units at volumes that local beach-only demand would not support. Source: madeirabeachfl.gov/rocpark
Independence Day fireworks over John's Pass (July). Madeira Beach Spring Break Rotary Carnival at R.O.C. Park (March). Eastern Michigan Madeira Beach Invitational softball tournament. Annual Eastern Michigan University Day at the Beach. Music events and festivals at R.O.C. Park and John's Pass throughout the year. Year-round live music at the John's Pass Boardwalk restaurants and bars.
Investor takeaway: Madeira Beach has genuine year-round event demand that partially offsets its seasonal revenue dip. The Veterans Boat Parade in November and the Festival of Lights in December are particularly important for investors evaluating low-season cash flow. Price premium around these dates, require minimum stays that span the event weekend, and build them into your proforma underwriting as reliably bookable nights rather than open vacancy.
When a global hospitality brand commits to a market, it validates what the data already shows. Two Marriott-flagged hotels are under active development in Madeira Beach as of 2026, both by the same local developer team (Bill Karns, Marcus Winters of Caddy's, and Jeff Beggins of Century 21).
161 condo-hotel rooms + 10 penthouse residences. 8 stories. 30,000 sq ft ground-floor retail and restaurants. Skybridge to Gulf beach. Site: 15000 Madeira Way. Demolition began early 2026, groundbreaking March 2026. Expected completion 2027. Source: St. Pete Rising, February 2026.
87 keys. 6 stories. Located at 129th Avenue East and Pelican Lane, directly across from John's Pass Boardwalk. 11,600 sq ft street-level retail. 268-car parking. Rooftop pool. Planned completion 2028. Condo-hotel units available for individual purchase and nightly rental. Source: St. Pete Rising, August 2025.
What this means for STR investors: hotel-quality competition will enter the market, but hotel construction at this scale also drives increased visitor traffic, dining and retail activation, and sustained tourism infrastructure that supports rental demand across the entire city.
Madeira Beach's guest profile skews toward families and multigenerational travel. The highest revenue uplifts by amenity category:
A $300 to $800 investment in baby and family amenities can reposition a listing's earning tier. Only 0.9% to 2.4% of listings currently offer these items, creating significant white space for new hosts who add them.
Yes. The entire city of Madeira Beach sits in or adjacent to FEMA-mapped Special Flood Hazard Areas. Most residential and commercial parcels are in Zone AE (1% annual chance flood) or Zone VE (1% annual chance flood with wave action), with VE applying primarily to the Gulf-facing strip. That said, understanding what that actually means for a condo buyer specifically is more nuanced than it sounds.
The vast majority of STR properties in Madeira Beach are condos, and condo associations typically carry a master insurance policy that includes property and flood coverage for the building and common elements. That master policy is one of the 13 documents you receive during your inspection period, and reviewing it carefully, including its flood coverage, deductibles, and replacement cost limits, is one of the most important steps in your due diligence. Many buildings are also elevated, which reduces their flood risk profile compared to single-story structures.
If you are financing the purchase, your lender will have specific insurance requirements. If you are paying cash, you have more flexibility about what individual coverage you carry beyond the condo master policy. Either way, the most useful thing you can do early in the process is request the building's master insurance policy from the seller and have a conversation with an insurance agent who has experience with Florida coastal STR condos. They can tell you exactly what the master policy covers, where gaps might exist, and what additional coverage, if any, makes sense for your situation.
Source: FEMA Flood Map Service Center, Pinellas County Flood Maps at pinellas.gov/flood-maps-zones.
Hurricane Helene (September 26, 2024) and Hurricane Milton (October 9, 2024) struck Pinellas County 13 days apart. Helene was a Category 4 that passed roughly 100 miles offshore but pushed a devastating storm surge into all the Gulf Beaches. Ground-floor units and single-story homes flooded. Access to the islands was cut off for days. The John's Pass Jetty and Walkway took damage. Recovery has been uneven and was still active in many areas six months after the storms.
On any Madeira Beach purchase in 2026, ask three specific questions: Did this property flood in Helene or Milton? What permits were pulled for post-storm repairs? Has any improvement work on the property triggered or approached the FEMA 50% Rule threshold?
FEMA's 50% Rule states that if a property is improved or repaired by more than 50% of its pre-improvement market value (excluding land), the entire structure must be brought into current floodplain code. In most cases, that means elevating the lowest finished floor to at or above base flood elevation plus Pinellas County's one-foot freeboard requirement. Elevation costs typically run $150,000 to $400,000 or more depending on the structure.
In Madeira Beach post-Helene and Milton, properties with significant storm damage and subsequent repairs are the highest-risk category for triggering this rule. Get the city's permit history in writing and have a structural engineer or experienced local inspector review any property with visible storm or flood damage before you close.
Insurance in Madeira Beach is more nuanced than a blanket checklist. Because almost all STR properties here are condos, and because condo associations carry master policies, your individual coverage situation depends heavily on what the building's master policy already covers. The best first step is requesting the master insurance policy as part of your inspection period documents and having a conversation with an agent who specializes in Florida coastal STR condos. They can walk you through what is covered at the building level, what additional coverage makes sense for your unit and your STR operation, and how your situation changes depending on whether you are financing or paying cash.
Standard homeowner policies typically exclude short-term rental activity. If you are operating as an STR, it is worth talking to an agent about whether your individual unit coverage addresses STR use, what the master policy already covers, and whether loss-of-rental-income coverage makes sense for your situation and risk tolerance. An agent experienced with Florida coastal condos will know what questions to ask.
Most Madeira Beach STR condos are elevated and covered under a condo association master policy that includes property and flood coverage. Request the master policy during your inspection period, review its deductibles and replacement cost limits, and ask your insurance agent whether additional individual coverage makes sense for your unit. Cash buyers have no lender requirement; financing terms vary by lender.
An umbrella liability policy is worth a conversation with your agent, particularly for units with pool access, dock access, or direct beach frontage. Many STR owners find the cost modest relative to the protection it provides. Your agent can help you weigh what makes sense for your specific property and guest profile.
No. Only condos in R-3, C-1, C-3, and C-4 zoned parcels can be legally rented on a short-term basis. Within those parcels, the HOA declaration and current board policies may impose a minimum-stay requirement longer than the city's. The combination of city zoning and HOA rules controls what you can do. Verify both, in writing, before you write an offer.
The highest-performing STR investment zones in Madeira Beach are the Gulf Boulevard corridor (R-3 or commercial zoned condo buildings from the south end near John's Pass through the north end), and the John's Pass Village Activity Center (C-1 zoning under Ordinance 2024-09) for the maximum walkability premium.
The Madeira Beach Yacht Club bay-side complex offers a different investor profile: lower price points and water access, but often with 7-day HOA minimum-stay requirements and lower rental demand than Gulf-front units. The interior residential streets, including the Crystal Island neighborhood, are R-1 zoned with a six-month minimum stay requirement and are not viable for short-term rentals. These areas are long-term rental or personal-use plays only.
Three steps in sequence: (1) Check the parcel's color on the city's Vacation Rental Restriction Map at madeirabeachfl.gov. If it is green, proceed to step two. If it is blue or red, confirm whether valid grandfather documentation exists or plan for long-term rental only. (2) Contact the Madeira Beach Planning Department at 300 Municipal Drive to confirm the current zoning designation in writing. Ask specifically whether any recent ordinance changes affect the parcel. (3) Request the HOA declaration, bylaws, and current board-approved rental policy during your inspection period. Confirm the minimum-stay requirement in writing from the association itself, not from the listing agent or seller.
Four things are unique to Madeira Beach: (1) The restriction map, which requires parcel-level zoning verification rather than a citywide rule check. (2) The 2006 ordinance history and the grandfather rights question, which require documentation proof rather than seller assurances. (3) Post-Helene and post-Milton flood damage history, which requires a permit review and 50% Rule assessment on any pre-2024-storm property. (4) Florida's 2025 condo disclosure law, which gives buyers a 7-business-day review period for 13 mandatory documents including the SIRS (Structural Integrity Reserve Study), Milestone Inspection report, Master Insurance policy, and Special Assessment disclosure for any assessment discussed in the past 12 months.
Under Florida Statute 718.503 (revised, effective July 1, 2025), condo buyers now have a 7-business-day review period (extended from the previous 3 days) for 13 mandatory documents. Required disclosures include the Declaration of Condominium, current and proposed bylaws and rules, the most recent year-end financial statement, the most recent Milestone Inspection report, the Structural Integrity Reserve Study (SIRS) if required, Master Insurance policy summary, and a Special Assessment disclosure covering any assessment approved or formally discussed in the past 12 months. Sellers who fail to provide required documents carry personal liability for costs arising from undisclosed conditions. The flood disclosure requirement (Florida Statute 689.302) took effect October 1, 2025. Ask for all 13 documents on day one of the inspection period.
Florida law now requires condominium buildings that are three stories or taller and 30 years or older to undergo a Milestone Inspection, a structural integrity review by a licensed engineer or architect. In Madeira Beach, the vast majority of the STR-eligible condo inventory was built between 1950 and 1988, which means most buildings either have already completed a Milestone Inspection or are currently required to do so.
A Phase 1 Milestone Inspection is a visual review. If concerns are found, a Phase 2 inspection requires destructive or invasive testing. Buildings that fail Phase 2 may face mandatory repairs and special assessments that can run hundreds of thousands of dollars per unit.
Request the most recent Milestone Inspection report as part of your 13-document inspection period disclosure. If the report is unavailable, ask when the building's inspection was last completed and whether Phase 2 was triggered. A missing or overdue Milestone Inspection is a red flag. The Surfside collapse in 2021 is the reason this law exists.
Florida law now requires condo associations of buildings three stories or taller to conduct a Structural Integrity Reserve Study (SIRS). The SIRS identifies the estimated remaining useful life and replacement cost for major structural components, including the roof, load-bearing walls, floor and ceiling systems, plumbing, electrical, waterproofing, windows, and any other components that, if they failed, could threaten the building's structural integrity.
Associations are now required to fully fund the reserves identified in the SIRS. A building with a recently completed SIRS that shows large unfunded reserve deficits may face a significant special assessment in the near term. Before you buy, review the SIRS report and ask the association: (1) Are reserves currently funded to the SIRS-required level? (2) Has the board voted on or discussed any special assessments to address reserve shortfalls? (3) What is the current monthly HOA assessment per unit and has it increased in the past 24 months? Any significant increase in HOA fees or a recently voted special assessment must be disclosed under the 2025 condo law's 12-month lookback.
Yes. The current STR-eligible condo inventory in Madeira Beach includes several newer buildings that avoid the Milestone Inspection and deep reserve-funding concerns that affect older Gulf Boulevard stock. From the April 2026 StellarMLS data, STR-eligible options built in the last 20 years include: Madeira Bay Resort I (2020), Harbor at Town Center (2020 and 2022), The Residences at Town Center (2024), Madeira Del Mar (2021), Snug Harbour (2003), and Madeira Bay Resort II (2006).
At the luxury end, Gulf Shores 2nd Add on Gulf Boulevard has 2024-2026 construction units listed at $2.7M to $2.8M. Looking further ahead, the two Marriott-flagged condo-hotel projects under development (The Beachmaker and the Marriott Tribute at John's Pass) will add brand-new STR-eligible inventory at the luxury tier, with units in The Beachmaker available for purchase in the Marriott condo-hotel program. These will operate under Marriott's global reservation system, giving owners access to Bonvoy bookings alongside direct vacation rental revenue.
The most valuable thing a Madeira Beach STR seller can provide is verified, documented rental history from a trusted source, not self-reported spreadsheets. Pull the prior 24 to 36 months of rental revenue from your property management platform or booking platform records. Present gross revenue, occupancy rates, and average daily rate by month so a buyer can see the full seasonal pattern, including both March and September. Presenting this data transparently, with the low-season months included, builds more credibility than a cherry-picked annual summary.
Additionally have ready: the current Business Tax Receipt, DBPR vacation rental license, flood insurance policy and current Elevation Certificate, the most recent Milestone Inspection report for the building, the SIRS report if applicable, HOA documents with current minimum-stay policy and HOA financials, and a full 12-month special assessment history. Under Florida's 2025 condo law, buyers have a 7-business-day review period. Sellers who have all 13 documents ready on day one eliminate one of the most common renegotiation triggers.
The April 2026 STR-eligible condo market in Madeira Beach is clearing at a median 95% of list price after a median 55 days. That is a seller's market at or just below asking, not at significant premiums. Overpriced listings in this market sit, and the CMA shows active listings with CDOM over 400 days. Price at or just below market for your building and bedroom count, lead with your documented rental income, and present the seasonal revenue data honestly including off-season months. Buyers who understand STR underwriting trust transparent data over optimistic summaries. An experienced STR listing agent presents the income story in a way that supports your price rather than triggering an investor's discount instinct.
Three things regularly surprise Madeira Beach STR sellers: (1) Insurance documentation. Sophisticated buyers and their advisors often ask to see the building's master insurance policy early in the process, along with a CLUE report on the individual unit. If a unit has prior flood claims, those show up on the CLUE report and may affect a buyer's conversation with their insurance agent. Having these documents organized before you list speeds things up considerably. (2) SIRS and Milestone status. Buyers with advisors are asking about both documents before they write an offer, not after. If your building's SIRS shows a large unfunded reserve deficit, a knowledgeable buyer will price that risk into the offer. Get ahead of it by knowing the numbers yourself. (3) Post-Helene and Milton permit history. If your unit or building had work done after the 2024 storms, buyers will pull the permit record. Have the paperwork organized and be able to explain what was repaired, what permits were pulled, and whether any FEMA 50% Rule threshold questions were raised.
This is one of the more nuanced STR seller questions in Madeira Beach. Keeping bookings on the calendar through closing has two benefits: it maintains revenue continuity and it gives buyers live proof of demand. The downside is that showing flexibility and timing become more complicated when future guests are committed. The standard approach is to honor existing bookings and block new bookings for a 30-day window post-closing to give the buyer an unencumbered transition. Discuss this with your listing agent before you go live. A well-structured STR sale coordinates the listing timeline, booking calendar, and closing date so revenue is maintained without creating a mess for the buyer's first month of ownership.
"The sellers who get the best outcomes in Madeira Beach are the ones who treat the sale like a business transaction, not just a real estate transaction. Documented rental income, clean disclosures, the restriction map and HOA docs ready to go, and a clear story about what the property has earned and can earn. That package shortens the inspection period and limits the renegotiation conversation significantly."
Cyndee and her husband Jack have lived on the Pinellas Gulf Beaches since 1991, over 35 years, and raised their two Florida-native sons, both born in Clearwater Beach, here on the sand. The name Sandbars to Sunsets is not a tagline, it is where their family grew up. They have owned waterfront property in Madeira Beach since 2018, both a condo and a home, which means Cyndee advises buyers from direct personal experience, not just professional knowledge. With 435+ residential transactions, $230M+ in sales, and 150+ vacation rental and STR closings, she is the Gulf Beaches' leading STR investment specialist. She serves as 2026 Treasurer of Florida Realtors, 2026 Chair of the NAR Regulatory Issues Forum, and former Chair of the NAR Insurance Committee.
Cyndee will pull the restriction map, verify the zoning, review the HOA rental policies, and give you an unfiltered STR eligibility assessment at no cost, before you write an offer. Call (727) 710-8035 or visit SandbarToSunsets.com.