Last updated: May 17, 2026
The Madeira Beach short-term rental market in May 2026 is showing 68 active STR-eligible listings, an 11-closing April, and a median sold price of $725,000 — with Airbnb revenue up 25.8% year over year. If you are evaluating a vacation rental condo or beach rental property purchase in Madeira Beach, here is what the current data actually shows, what it means for buyers, and what to verify before any offer.
I am Cyndee Haydon, a Madeira Beach resident and waterfront property owner since 2018. I hold both a waterfront condo and a waterfront home in the city. I also hold the RSPS (Resort and Second-Home Property Specialist) designation and have closed 62 STR-friendly properties in the past five years across the Pinellas Gulf Beaches. The full Madeira Beach STR investment guide, with the complete list of 42 STR-eligible buildings, zoning rules, and the Haydon SHORE™ Framework applied to this market, is at pinellasgulfbeachstrinvestment.com/madeira-beach/.
What the May 2026 Madeira Beach STR Market Data Shows
Source: StellarMLS, STR-eligible properties only, data pulled May 2026. These numbers cover properties that legally allow rentals of one month or less — not all Madeira Beach listings.
- Active STR-eligible listings: 68
- Pending sales: 8
- April 2026 closings: 11
- Median sold price: $725,000
- Median sold-to-list ratio: 95.0%
- Median days on market: 55
- Median price per square foot: $604
The 95% sold-to-list ratio tells you this is a negotiating market, not a bidding war market. Buyers who are patient and prepared are finding room. Sellers still anchored above market are sitting — 55 days is not a fast market.
What Airbnb and VRBO Operators Are Actually Earning in Madeira Beach
Source: AirROI 2026 dataset, May 2025 through April 2026, 731 active Madeira Beach listings.
- Average annual gross revenue: $35,963
- Average daily rate: $311
- Average occupancy: 39.4%
- Revenue growth year over year: +25.8%
- Top 10% of listings earn: $9,244 or more per month
- Top 25% of listings earn: $6,265 or more per month
- Peak month: March
- Lowest month: September
The 25.8% year-over-year revenue growth is the headline number. That is not a projection — it is what operators with active Madeira Beach vacation rentals actually earned compared to the prior year. The market average of $35,963 is the floor. Well-positioned properties near John’s Pass, with professional management and strong guest reviews, consistently outperform it.
The Zoning Rule Every Madeira Beach Vacation Rental Buyer Needs to Understand First
Madeira Beach does not have a single citywide ordinance that permits or prohibits short-term rentals. It uses a zoning map. Whether a specific property legally allows nightly or weekly rentals depends entirely on its zoning designation.
- R-3, C-1, C-3, C-4 zones: Short-term rentals allowed
- R-1 zone: Six-month minimum stay required
- R-2 zone: Three-month minimum stay required
I have seen buyers fall in love with a Madeira Beach beach rental condo only to discover the building sits in an R-2 zone where their intended Airbnb operation is not permitted. The listing may not disclose this clearly. Verify the zoning designation on every property before you write an offer — not during inspection, not after. The city’s restriction map is public record.
Beyond city zoning, individual HOA documents override city rules when more restrictive. A building in an R-3 zone can still prohibit short-term rentals in its Declaration of Condominium. I verify both layers on every Madeira Beach STR purchase I represent.
Why John’s Pass Location Within Madeira Beach Determines Your Revenue
Madeira Beach is two and a half miles long. Not all of it performs the same as a vacation rental market.
John’s Pass — the inlet carved by the Great Gale of 1848 — is the only Gulf of Mexico boat access between Clearwater Beach and St. Pete Beach on the Intracoastal Waterway. Every fishing charter, dolphin tour, and recreational boater heading to open Gulf waters from this stretch of the coast passes through John’s Pass. That concentration of activity, combined with an 1,100-foot boardwalk with 100-plus merchants and restaurants, creates a walkability premium that translates directly into higher nightly rates and occupancy for vacation rentals within half a mile.
Madeira Beach is nicknamed the “Grouper Capital of the World.” It also hosts one of the largest resident bottlenose dolphin populations in the Tampa Bay area — visible from the boardwalk and from shore year-round. These are not marketing claims. They are guest experience drivers that generate five-star reviews and repeat bookings, particularly for family travelers who are the primary STR demand segment in this market.
The R.O.C. Park softball and baseball tournaments are a less-discussed demand driver. Tournament weekends fill Madeira Beach Yacht Club units in months that would otherwise see soft occupancy. Year-round event demand is part of what makes this market different from quieter Gulf Beach communities to the north.
Frequently Asked Questions: Madeira Beach Vacation Rental Investment
Q: Can I buy a condo in Madeira Beach and list it on Airbnb?
A: It depends on two things: the city zoning designation of the building and the HOA documents. Properties in R-3, C-1, C-3, and C-4 zones are eligible for short-term rentals under city rules. Properties in R-1 and R-2 zones have minimum stay requirements of six months and three months respectively, which effectively prohibit Airbnb-style nightly and weekly rentals. Even in an eligible zone, the condo association’s Declaration of Condominium may impose its own minimum stay, owner waiting period, or rental cap. Both layers must be verified before any offer. My full list of 42 confirmed STR-eligible buildings in Madeira Beach is at pinellasgulfbeachstrinvestment.com/madeira-beach/.
Q: How much does a Madeira Beach vacation rental make per year?
A: The AirROI 2026 market average across 731 active Madeira Beach listings is $35,963 in annual gross revenue, at a $311 average daily rate and 39.4% occupancy. Top-performing properties earn $9,244 or more per month. The 25.8% year-over-year revenue growth rate reflects real operator earnings, not projections. Properties within walking distance of John’s Pass Village and Boardwalk consistently outperform the market average due to the walkability premium, fishing charter access, dolphin tour proximity, and year-round event demand. Source: AirROI dataset, May 2025 through April 2026.
Q: What is the current Madeira Beach vacation rental market like for buyers in 2026?
A: As of May 2026, there are 68 STR-eligible active listings, 8 pending sales, and 11 closings in April. The median sold price was $725,000 at a 95% sold-to-list ratio with 55 median days on market. This is a patient buyer’s market where correctly priced properties move and overpriced properties sit. Buyers with clear investment criteria and verified zoning are finding negotiating room. Source: StellarMLS, May 2026.
Q: Is Madeira Beach a good place to invest in a vacation rental property?
A: Madeira Beach has specific characteristics that make it one of the stronger Pinellas Gulf Beach STR markets: daily and weekly rentals are permitted in commercial and R-3 zones with no minimum stay requirement in those zones, revenue grew 25.8% year over year, and John’s Pass creates year-round demand that seasonal-only beach markets cannot replicate. The complexity is the zoning map — unlike Indian Rocks Beach, where short-term rentals are allowed in all residential zones, Madeira Beach requires zone-by-zone verification. Buyers who do that verification and buy in the right zone with the right HOA documents are entering a market with documented income growth and a significant supply of activity-driven demand.
The Haydon SHORE™ Framework Applied to Madeira Beach
I evaluate every Madeira Beach STR investment through five factors:
- S — Supply and Demand: 68 active STR-eligible listings, 25.8% revenue growth, March peak, September low
- H — Hosting and Rental Rules: Zoning map governs eligibility, HOA documents override city rules, annual registration required
- O — Operating Economics: $311 ADR, 39.4% occupancy, 6% TDT, standard Florida sales tax, condo master policies typically cover flood for most buildings
- R — Risk and Resilience: Entire city in FEMA flood zone AE or VE, most STR units are condos with master policies, elevated buildings reduce individual exposure
- E — Experience and Earnings Potential: John’s Pass walkability premium, dolphin and fishing access, R.O.C. Park tournament demand, Festival of Lights December demand driver
The full framework applied to Madeira Beach, with the complete 42-building STR-eligible list and current market data, is at pinellasgulfbeachstrinvestment.com/madeira-beach/.
Bottom Line: The Madeira Beach vacation rental market in May 2026 shows 25.8% revenue growth year over year, 68 STR-eligible active listings, and a $725,000 median sold price at 95% of list. The zoning map is the first thing to verify on any Madeira Beach Airbnb investment — and the second is the HOA documents. Get both right and you are entering a market with John’s Pass proximity, year-round dolphin and fishing demand, and documented income growth that few Gulf Beach communities can match.
If you are evaluating a vacation rental property in Madeira Beach or anywhere on the Pinellas Gulf Beaches, I am reachable at (727) 710-8035 or at sandbarstosunsets.com. Every inquiry is handled personally.
Cyndee Haydon, CRS, ABR, SRS, RENE, RSPS, CLHMS, CIPS, SRES | Sandbars to Sunsets Team | Future Home Realty | Madeira Beach Resident and Waterfront Property Owner Since 2018