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.
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City Profile
Unlike most of its neighbors, Madeira Beach, nicknamed "Mad 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. The city slogan, "Two miles long and a smile wide," captures the place perfectly: compact, coastal, genuinely welcoming.
Because sub-30-day rentals are limited by zoning, eligible inventory is structurally constrained. AirROI's 2026 dataset shows what that does in practice: supply grew 26.5% in a year, and revenue still grew 25.8%. Demand keeps absorbing what zoning allows to exist.
"Madeira Beach is the market where I most often have to stop a buyer from writing an offer the same day. Not because the property is wrong, but because nobody has verified the zoning district yet. In Indian Rocks Beach the city says yes everywhere and the HOA is the question. In Madeira Beach the district is the first question, the grandfathered file is the second, and the HOA documents are the third. The buyers who win here are the ones who verify all three before they fall in love."Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES · Madeira Beach Resident and Waterfront Property Owner Since 2018 · Sandbars to Sunsets Team · Future Home Realty
The Rules Hub
Properties advertised on Airbnb and VRBO in restricted districts may be operating illegally. Code enforcement in Madeira Beach leads to the Special Master, fines of $250 per day, and property liens that travel with the deed. Verify the parcel on the map and confirm in writing with the Madeira Beach Community Development Department, (727) 391-9951, before closing.
| Zone | Name | STR Status | City Min. Stay | Best Investment Use |
|---|---|---|---|---|
| R-1 | Single-Family Residential | Prohibited | 6 months | Annual lease, personal use |
| R-2 | Low Density Multifamily | Prohibited | 3 months | Snowbird seasonal lease |
| 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 (Ord. 2024-09) | High-walkability STR, mixed-use |
| C-3 | General Commercial | Allowed | None | STR above ground-floor commercial |
| C-4 | Marine Commercial | Allowed | None | Marina-adjacent STR |
Source: Madeira Beach Code of Ordinances, Sections 110-176 (R-1), 110-201 (R-2), 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.
| When | What Happened | Investor Implication |
|---|---|---|
| Pre-2006 | No formal STR ordinance. Short-term rentals operated broadly across the city. | Some owners claim grandfather status. Documentation requirements are strict. |
| 2006 | City bans STR in R-1 and R-2 residential zones to protect neighborhood character. This is the origin of the current 6-month minimum in R-1 and 3-month minimum in R-2. | Properties operating STR in restricted zones after 2006 without verified grandfather documentation were doing so illegally from that date. |
| June 1, 2011 | Florida passes FS 509.032(7)(b) prohibiting new local STR restrictions but expressly exempting all ordinances adopted before that date. Madeira Beach's 2006 restrictions are permanently grandfathered under state law. | The R-1 and R-2 restrictions are legally permanent and cannot be overridden by future state action. Plan investments around them as fixed. |
| 2015-2016 | City enforcement wave: 100+ properties cited. Every Special Master case resulted in a finding of violation. $250/day fines plus legal fees. Unpaid fines became property liens. (Tampa Bay Times, April 28, 2016) | The city will enforce. Active Airbnb listings are treated as primary evidence of violation. No neighbor complaint is required to trigger investigation. |
| Sept. 11, 2018 | Ordinance No. 2018-01 adopted, codified as Section 110-843. Establishes current compliance framework including Business Tax Receipt, annual renewal, posted registration, and safety standards. | All current STR compliance questions trace to this ordinance. Use Section 110-843 as the controlling reference. |
| Aug. 24, 2021 | City publishes the official color-coded Vacation Rental Restriction Map at madeirabeachfl.gov. Green = STR allowed. Blue = 90-day min. Red = 6-month min. | The map is your first due diligence tool. Green does not mean the HOA allows it. Verify both layers before purchase. |
| 2024 | Ordinance 2024-09 replaces C-1 Tourist Commercial with the John's Pass Village Activity Center, creating six 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; Florida Statute 509.032(7)(b); Vacation Rental Restriction Map (August 24, 2021, madeirabeachfl.gov); Tampa Bay Times, April 28, 2016; Pinellas Realtor Organization.
A grandfather exemption requires documentation of all four of these: (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; (4) sales tax has been paid on all rental income throughout the period. If the seller cannot produce all four elements, assume the grandfathering does not exist. Grandfathered status may not transfer automatically on sale. Confirm in writing with the Madeira Beach Community Development Department, (727) 391-9951, before closing.
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. 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. Always read the full declaration and current board-adopted rules before hosting a single guest.
Market Data
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. September will test whether the numbers actually pencil. The investors who sleep well in October are the ones who modeled both months before they wrote their offer."Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES · Sandbars to Sunsets Team · Future Home Realty
The John's Pass Premium
John's Pass was carved on September 27, 1848 by the Great Gale of 1848, permanently separating Madeira Beach from Treasure Island. Named after John LeVique, a French sailor and turtle fisherman who first navigated the new inlet, the pass is the only Gulf of Mexico boat access between Clearwater Beach and St. Pete Beach on the Intracoastal Waterway. This geographic fact makes Madeira Beach the fishing charter hub of the Pinellas Gulf Beaches and explains why the area is nicknamed "Grouper Capital of the World."
Today 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, that proximity is a measurable revenue premium, not a subjective nice-to-have.
John's Pass is also home to one of the largest resident bottlenose dolphin populations in the Tampa Bay area. Pods are spotted daily from the boardwalk, from shore near Eleanor Island, and from the beach itself. This is a genuine guest experience driver that generates 5-star reviews and repeat bookings year-round.
A three-day October event that is the largest annual STR demand spike in Madeira Beach. Properties within walking distance of John's Pass command their highest Q4 weekend rates during this event.
Organized since 1996. Runs on the Saturday closest to Veterans Day. Decorated boats parade through Madeira Beach waterways raising funds for veteran charities. A proven November booking driver when demand otherwise dips. Source: veteransboatparade.org
Celebrating its 60th year in 2026. Decorated boats parade through Boca Ciega Bay with the finale at John's Pass Boardwalk at approximately 9:45–10 PM. A dependable December demand driver for STR units with bay views or boardwalk proximity.
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 in 2026:
The Beachmaker (Marriott Autograph Collection) — 161 condo-hotel rooms, 10 penthouse residences, 8 stories, 30,000 sq ft retail. 15000 Madeira Way. Groundbreaking March 2026. Expected 2027.
Marriott Tribute Portfolio at John's Pass — 87 keys, 6 stories, rooftop pool, 11,600 sq ft street-level retail. At 129th Avenue East and Pelican Lane. Planned 2028 completion.
Source: St. Pete Rising, February 2026; August 2025. Hotel construction at this scale drives increased visitor traffic and sustained tourism infrastructure that supports rental demand across the entire city.
The Haydon SHORE™ Framework
Every Madeira Beach property Cyndee Haydon's clients evaluate goes through the Haydon SHORE™ STR Investment Framework, a five-factor methodology covering Supply and Demand, Hosting and Rental Rules, Operating Economics, Risk and Resilience, and Experience and Earnings Potential, before any offer is written.
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. John's Pass walkability creates a demand floor no supply increase can eliminate. Source: AirROI 2026.
Zoning controls everything. Confirm the parcel is green (R-3 or commercial) on the city's Vacation Rental Restriction Map before negotiating. Then verify the condo HOA's minimum-stay policy, which is often stricter than the city's. HOA rules override city rules when they are more restrictive. The Declaration and board-adopted rules are the controlling documents.
Underwrite to the median, not the average. Budget 13% total tax on gross revenue. STR-specific insurance. Property management (10-20% of revenue). HOA fees ($500-$1,500/month). Clean reserves for September and October. For condos, the master association policy typically covers building-level flood and property coverage.
The entire city of Madeira Beach sits in FEMA-mapped Special Flood Hazard Areas (Zone AE or Zone VE). Hurricane Helene (September 26, 2024) and Milton (October 9, 2024) struck 13 days apart. On any purchase: Did this property flood? What permits were pulled? Does cumulative improvement approach the 50% threshold? Cyndee navigated the 50% Rule herself as a Madeira Beach homeowner.
Top 10% of listings earn $9,244+/month. These require John's Pass proximity for the walkability premium, professional photography, 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.
Compliance
Apply at Madeira Beach City Hall, 300 Municipal Drive. Renews annually. Must be posted visibly at the rental property.
Issued by the Florida DBPR 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. Note: Airbnb and VRBO collect and remit state sales tax for platform bookings automatically. For direct bookings, the owner is responsible.
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 platform bookings. For direct bookings, the owner is responsible for collecting and remitting 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.
Collection allowance: owners who file and pay TDT electronically and on time may deduct 2.5% of the tax collected, up to $30 per filing period. File on time to qualify.
StellarMLS · STR-Eligible Properties Only
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.
Condo-Hotel properties are flagged separately. Many conventional mortgage lenders will not finance a condo-hotel purchase. These properties 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 | Recent Sold Price (1,000-day MLS) | Waterfront |
|---|---|---|---|---|---|
| Gulf Lane — South End (John's Pass Area) | |||||
| Beach Place Condominiums | 12901 Gulf Ln | Condo | — | $647,000 (Mar 2025) | Yes |
| Crimson on the Gulf Condo | 12935 Gulf Ln | Condo | 1994 | $825,000 (Apr 2026) | Yes |
| Madeira Norte Condos | 13000 Gulf Ln | Condo | — | $900,000 (Jan 2024) | Yes |
| Princess Condominiums | 13398 Gulf Ln | Condo | — | $1,555,000 (Feb 2024) | Yes |
| Gulf Blvd — South (12xxx–13xxx) | |||||
| Sandy Shores Condo | 12924 Gulf Blvd | Condo | 1979 | $675,000 (Nov 2023) | Yes |
| Madeira Bay Resort I | 13101 Gulf Blvd | Condo-Hotel | 2020 | $595,000 (Oct 2025) | Yes |
| Madeira Bay Resort II | 13235 Gulf Blvd | Condo-Hotel | 2006 | $500,000 (Oct 2025) | Yes |
| Chambre The Condo | 13336 Gulf Blvd | Condo | 1988 | $530,000 (Apr 2026) | Yes |
| Bellarte on the Gulf | 13630 Gulf Blvd | Condo | 2007 | $3,050,000 (Mar 2026) | Yes |
| Madeira Sands Condo | 13650 Gulf Blvd | Condo | 1980 | $1,150,000 (Aug 2024) | Yes |
| Villa Madeira Condo | 13720 Gulf Blvd | Condo | 1981 | $1,050,000 (May 2024) | Yes |
| Skyline of Madeira | 13999 Gulf Blvd | Condo-Hotel | — | $600,000 (Jul 2024) | Yes |
| Gulf Blvd — Central (14xxx) | |||||
| Beach Club of Madeira | 14010 Gulf Blvd | Condo | — | $3,000,000 (Dec 2023) | Yes |
| Arena De Madeira Condominiums | 14110 Gulf Blvd | Condo | — | $998,000 (Dec 2023) | Yes |
| Gulf Gardens Motel Apts Condo | 14141 Gulf Blvd | Condo | — | $310,000 (Dec 2023) | No |
| Trillium Condo | 14146 Gulf Blvd | Condo | 1981 | $785,000 (Apr 2026) | Yes |
| Tropic Shores Apt Motel Condo | 14251 Gulf Blvd | Condo-Hotel | 1958 | $300,000 (Nov 2024) | No |
| Kima Condominiums | 14300 Gulf Blvd | Condo | — | $795,000 (Jan 2026) | Yes |
| La Coquina Condominiums | 14401 Gulf Blvd | Condo | — | $600,000 (Mar 2025) | No |
| Arie Dam Condo | 14600 Gulf Blvd | Condo | 1984 | $880,000 (May 2026) | Yes |
| The Seaview Condominiums | 14700 Gulf Blvd | Condo-Hotel | — | $1,050,000 (May 2024) | No |
| Las Brisas of Madeira Condo | 14710 Gulf Blvd | Condo | 1981 | $1,050,000 (May 2025) | No |
| Madeira Place Condo | 14001 Gulf Blvd | Condo | 1981 | $339,500 (Feb 2025) | No |
| Madeira Vista Condominiums | 14800 Gulf Blvd | Condo | — | $635,000 (May 2024) | No |
| Gulf Blvd — North (14900–15462) | |||||
| Surfside South Condo | 14900 Gulf Blvd | Condo | 1980 | $811,000 (May 2024) | Yes |
| Ocean Sands One Condo | 14950 Gulf Blvd | Condo | 1980 | $740,000 (Sep 2024) | Yes |
| Ocean Sands Two Condo | 15000 Gulf Blvd | Condo | 1981 | No recent closed sales | Yes |
| Gulf Shores 2nd Add (new construction) | 14048 Gulf Blvd | Condo | 2024–2026 | $2,799,000 (May 2026) | Yes |
| Madeira Towers Condo | 15316 Gulf Blvd | Condo | 1978 | $755,000 (Jan 2025) | Yes |
| Shores of Madeira Condo | 15400 Gulf Blvd | Condo | 1977 | $790,000 (Sep 2025) | Yes |
| Surfside Tower Condo | 15462 Gulf Blvd | Condo | 1978 | $1,275,000 (Sep 2023) | Yes |
| Town Center Area (150th Ave) | |||||
| Harbor at Town Center | 300 150th Ave | Condo | 2020–2022 | $660,000 (May 2025) | Yes |
| Madeira Cove Condo | 399 150th Ave | Condo | 1997–1999 | $600,000 (Jan 2024) | Yes |
| The Residences at Town Center | 400 150th Ave | Condo | 2024 | $1,000,000–$1,238,525 (2024–2026) | No |
| Boca Vista Condominium | 401 150th Ave | Condo | 1983 | $577,000 (May 2024) | Yes |
| Snug Harbour Condo | 423 150th Ave | Condo | 2003 | $949,000 (Oct 2023) | Yes |
| Aljean Shores Condo | 54 154th Ave | Condo | — | $479,000 (Oct 2023) | No |
| Other STR-Eligible Addresses | |||||
| Madeira Del Mar Condo | 15305 1st St E | Condo | 2021 | $942,500 (Mar 2024) | No |
| Madeira Beach Yacht Club | 165 Medallion Blvd | Condo | 1973 | $345,000 (May 2026) | No |
| Sea Breeze of Madeira Condo | 13500 Gulf Blvd | Condo | 1982 | $887,500 (Dec 2024) | Yes |
| Collwood The Condo | 13440 Gulf Blvd | Condo | 1981 | $940,000 (Mar 2024) | Yes |
| Wave Resort Condo | 13343 Gulf Blvd | Condo | 1950 | $195,000 (Jul 2024) | No |
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.
Risk & Resilience
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 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 approached the FEMA 50% Rule threshold?
Cyndee Haydon and her husband Jack are Madeira Beach homeowners. Their property flooded in Hurricane Helene in September 2024. In the months that followed, they navigated the 50% Rule compliance process themselves, coordinating with city officials, carefully managing the permitted repair scope, and ultimately returning home. During that same period, they helped neighbors on their street do the same, including some with more significant damage.
Source: Cyndee Haydon, personal experience navigating FEMA 50% Rule compliance in Madeira Beach, 2024 to 2025.
June 1, the first day of hurricane season. Every room from the doorway. Every exterior wall. Every appliance, piece of furniture, and custom improvement. Insurance companies need photos, not video, as proof of pre-storm condition. Store photos off-site in iCloud, Google Photos, or Dropbox. Photos stored only on a local device that floods are lost exactly when you need them most.
Cyndee Haydon offers to help Madeira Beach neighbors with their annual home photo documentation at no cost. Call (727) 710-8035.
Buyer FAQ
Four things are unique to Madeira Beach: (1) The restriction map, which requires parcel-level zoning verification rather than a citywide rule check, unlike Indian Rocks Beach where STRs are allowed in all residential zones. (2) The 2006 ordinance history and 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, Milestone Inspection report, master insurance policy, and special assessment disclosure for any assessment discussed in the past 12 months.
Florida law requires condo associations of buildings three stories or taller to conduct a Structural Integrity Reserve Study (SIRS) identifying the estimated remaining useful life and replacement cost for major structural components including roof, load-bearing walls, floor and ceiling systems, plumbing, electrical, and waterproofing. Associations are now required to fully fund reserves identified in the SIRS. A building with a SIRS showing large unfunded reserve deficits may face a significant special assessment. Before buying, review the SIRS and ask: Are reserves currently funded to the required level? Has the board voted on any special assessments to address shortfalls? What is the current monthly HOA assessment and has it increased in the past 24 months?
Yes. STR-eligible newer buildings 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 has 2024-2026 construction units listed at $2.7M to $2.8M. Looking ahead, the Marriott Beachmaker (Autograph Collection, 161 units, groundbreaking March 2026) and the Marriott Tribute Portfolio at John's Pass (87 keys, planned 2028) will add new STR-eligible condo-hotel inventory with access to Marriott Bonvoy global reservations.
Gulf-front condos command 30% to 50% higher nightly rates and fill faster during peak season. The tradeoff is higher acquisition price, higher wind and flood insurance, and VE zone FEMA designation on most Gulf-facing buildings. Bay-side and marina-adjacent condos offer lower entry price, dock access, and in the Madeira Beach market specifically, John's Pass proximity often matters more than a Gulf-facing position at comparable price points. A bay-side condo steps from the boardwalk and fishing charters can outperform a Gulf-facing unit two miles north because John's Pass is what many guests are specifically booking. Source: AirROI 2026 occupancy benchmarks by location within Madeira Beach.
No. The Business Tax Receipt, DBPR license, and tax accounts are owner-specific, and Airbnb and VRBO listings with their review history are personal to the host. The buyer establishes their own licenses and listings. What transfers is the property, any documented grandfathered status verified with the city, and the income records that prove performance. Sellers who package verified documentation protect their going-concern value and attract investor buyers at asking price.
Indian Rocks Beach permits nightly rentals citywide under Ordinance 2023-02 with no minimum stay, while Madeira Beach restricts sub-30-day rentals to commercial and tourist districts and grandfathered properties. IRB's market average revenue is higher ($64,338 vs. $35,963, AirROI 2026), reflecting a larger share of single-family homes with pools and a wider range of property types. Madeira Beach offers the John's Pass walkability premium and lower entry prices in several condo segments. District verification is the deciding step in Madeira Beach; building-level HOA verification matters in both. For a full comparison see the Madeira Beach vs. Indian Shores comparison page.
Monthly Market Intelligence
Every report is filtered to STR-eligible properties only, not all Madeira Beach condos. That distinction is what makes the data useful for vacation rental investment decisions. Published monthly with current StellarMLS transaction data and Cyndee Haydon's attributed market commentary.
Monthly StellarMLS data for STR-eligible condos and condo-hotels in Madeira Beach, the only publicly available report filtering this segment separately. Covers active listings, closings, median sold price, sold-to-list ratio, days on market, price per square foot, and Cyndee's market commentary.
Madeira Beach has a smaller single-family STR inventory than condos, but R-3 zoned canal and bay-front homes represent a distinct and less-tracked segment. This report will cover single-family STR-eligible homes separately from condo inventory when data volume supports monthly reporting.
Recognition & Rankings
Every recognition below is independently issued, attributed, dated, and sourced.
Cyndee and her husband Jack have lived on the Pinellas Gulf Beaches since 1991, over 35 years, and have owned waterfront property in Madeira Beach since 2018, both a condo and a home. That means Cyndee advises buyers from direct personal experience, not just professional knowledge. After Hurricane Helene flooded their property in 2024, they navigated the FEMA 50% Rule compliance process themselves, then helped neighbors on their street do the same. 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. The Sandbars to Sunsets Team does not manage vacation rentals. Every recommendation is conflict-free.
For Sellers
Have these ready before you list: the current Business Tax Receipt, DBPR vacation rental license, building master insurance policy, the most recent Milestone Inspection report, the SIRS if applicable, all 13 Florida 2025 condo disclosure documents, HOA rental policy and financials, and the post-storm permit history if the property had any repairs after Helene or Milton.
"The sellers who get the best outcomes in Madeira Beach treat the sale like a business transaction. Documented rental income, clean disclosures, the restriction map and HOA docs ready to go. That package shortens the inspection period and limits the renegotiation conversation significantly."Cyndee Haydon, CRS · Sandbars to Sunsets Team · Future Home Realty
A yard sign on an active Madeira Beach vacation rental tells every current guest and future booking inquiry that the property is for sale. Bookings stop converting. Revenue erodes at the moment you can least afford it. The Sandbars to Sunsets Team sells Madeira Beach vacation rentals through online marketing and targeted investor outreach, not yard signs.
Whether you are a buyer evaluating your first Madeira Beach vacation rental, a seller figuring out what your condo is worth, or a current owner with questions about the STR numbers, reach out. Every inquiry is handled personally. Cyndee Haydon is a Madeira Beach resident and waterfront property owner since 2018.