Key Takeaways — April 2026 Madeira Beach Condo STR Market
68 active STR-eligible listings. These numbers cover only zoning-verified, HOA-confirmed STR-eligible condos and condo-hotels — not all Madeira Beach condo inventory.
11 closings in April. Median sold price $725,000 at 95.0% of list price. Buyers are negotiating room below asking.
55 median days on market. $604 median price per square foot. Correctly priced properties are moving. Source: StellarMLS, April 2026.
Airbnb avg: $35,963/year. $311 ADR, 39.4% occupancy, revenue up 25.8% year over year. Source: AirROI 2026, 731 active listings.
5 condo-hotels in the 42-building list require portfolio financing — no conventional mortgage. Confirm financing type before any offer on a Madeira Beach condo.
Published by Cyndee Haydon, the most experienced STR specialist on the Pinellas Gulf Beaches. 150+ vacation rental transactions. (727) 710-8035.
Use this data to take your next step
Buying a Madeira Beach vacation rental?
Zoning map verification, HOA document review, condo vs condo-hotel financing, FEMA risk, and the full SHORE Framework applied to Madeira Beach.
Read the Buyer FAQ →
Selling a Madeira Beach vacation rental?
Income documentation, going concern sale structure, protecting your booking calendar, and how verified rental history drives sale price.
Read the Seller FAQ →
April 2026 Closed Sales
What the Madeira Beach STR Condo Market Did in April
These numbers come from StellarMLS and are filtered exclusively to condo and condo-hotel properties in Madeira Beach zoning districts that permit short-term rentals of one month or less. General Madeira Beach market reports include all condos regardless of STR eligibility — those numbers are not useful for vacation rental investors making acquisition decisions.
Active Listings
68
STR-eligible, May 2026
Pending Sales
8
Under contract
April Closings
11
Closed transactions
Median Sold Price
$725,000
April 2026 closings
Sold-to-List Ratio
95.0%
Buyers negotiating room
Median Days on Market
55
Median CDOM, April 2026
Price Per Sq Ft
$604
Median closed, April 2026
STR-Eligible Buildings
42
Confirmed, StellarMLS
Condo-Hotels
5
Portfolio financing required
Source: StellarMLS, STR-eligible condo and condo-hotel properties only, Madeira Beach, Florida. Data date: April 2026. Published May 2026 by Cyndee Haydon, Sandbars to Sunsets Team, Future Home Realty.
Airbnb & VRBO Income Benchmarks
What Madeira Beach Vacation Rental Condos Are Earning
AirROI's 2026 dataset, which tracks 731 active Madeira Beach listings across Airbnb and Vrbo from May 2025 through April 2026, shows strong and accelerating performance in the Madeira Beach vacation rental condo market. Revenue grew 25.8% year over year despite a 38.9% increase in supply — meaning demand is outpacing new inventory.
$35,963
Avg Annual Revenue
+25.8%
Revenue Growth YoY
Top Performer Benchmarks
Top 10%: $9,244+/month
Top 25%: $6,265+/month
Median: $3,659/month
Seasonality
Peak month: March ($8,896 avg)
Lowest month: September ($2,747)
Booking lead time: 77 days avg
Source: AirROI 2026 dataset, May 2025 through April 2026, 731 active Madeira Beach listings across Airbnb and Vrbo.
Know Before You Buy
Condo vs Condo-Hotel: A Critical Distinction for Madeira Beach Buyers
⚠ Condo-Hotel Properties Require Different Financing
Five buildings in Madeira Beach operate as condo-hotels: Madeira Bay Resort I, Madeira Bay Resort II, Skyline of Madeira, Tropic Shores Apt Motel Condo, and The Seaview Condominiums. These units require portfolio or commercial financing — no conventional Fannie Mae or Freddie Mac mortgage. Confirm your financing type before writing any offer on a Madeira Beach condo.
Both structure types produce vacation rental income in Madeira Beach. The right choice depends on your financing situation, personal use goals, and tolerance for shared management. Neither is universally better — the analysis requires looking at the specific building, specific HOA terms, and specific income history before any recommendation.
Location Within the City
The John’s Pass Proximity Premium
John's Pass is the only Gulf of Mexico boat access between Clearwater Beach and St. Pete Beach on the Intracoastal Waterway. The 1,100-foot boardwalk, 100-plus waterfront merchants and restaurants, fishing charter departures, dolphin tours, and the Grouper Capital of the World identity create year-round guest demand that properties elsewhere in Madeira Beach cannot replicate.
In the April 2026 closed transaction data, condos within walking distance of John's Pass Village moved faster and closer to list price than the northern end of the city. The three annual event demand spikes — John's Pass Seafood Festival (October), Veterans Boat Parade (November), and Festival of Lights Boat Parade (December 13, 2026) — are concentrated in this corridor and generate Q4 bookings that push annual revenue meaningfully above the AirROI market average of $35,963.
If your purchase analysis does not account for where within Madeira Beach the property sits, you are working from incomplete data.
Frequently Asked Questions
Madeira Beach Condo STR Market — May 2026
Is now a good time to buy a Madeira Beach vacation rental condo?
The April 2026 data shows 68 active listings, 8 pending, and 11 closings at a 95% sold-to-list ratio after 55 days. That is a buyer-favorable market with real negotiating room. Buyers with verified financing, confirmed zoning, and clear investment criteria are finding well-priced inventory. The John's Pass corridor buildings are moving faster — buyers targeting that corridor should not wait for conditions to improve further. Contact Cyndee Haydon at (727) 710-8035 for a current building-by-building analysis.
Is now a good time to sell a Madeira Beach vacation rental condo?
Sellers pricing at current market are achieving 95% of list in 55 days. The window is open for correctly positioned properties. Sellers anchored to 2022 peak pricing are accumulating days and eventually taking reductions. A verified 24-month income record presented alongside the listing consistently produces better outcomes than a residential-only listing approach for Madeira Beach vacation rentals. Contact Cyndee Haydon at (727) 710-8035 for a current pricing analysis.
What should I verify before making an offer on a Madeira Beach condo?
Three verifications before any offer — in this order. First: the parcel's zoning designation. Check the city's Vacation Rental Restriction Map at madeirabeachfl.gov. Green means proceed. Blue or red means restricted minimum stays. Second: the HOA Declaration of Condominium and current board-approved rental policy, in writing from the association. Third: whether the building is a condo-hotel requiring portfolio financing or a residential condo eligible for conventional financing. Confirm financing type with your lender before you write the offer, not during inspection period. Source: Madeira Beach Ordinance No. 2018-01, Section 110-843; Florida Chapter 718.
What is the best-performing property type for STR investment in Madeira Beach?
Gulf-front 2-bedroom condos in the John's Pass corridor are the highest-demand configuration in Madeira Beach — direct beach access, sunset balcony, walkable to the boardwalk. They command the highest nightly rates and fastest booking velocity. The tradeoff is the highest acquisition price and greatest flood insurance exposure in VE zones. For buyers at lower price points, bay-side condos within a quarter-mile of John's Pass outperform their price point in real occupancy data because the walkability premium matters more than the view premium at comparable prices. Source: AirROI 2026 benchmarks; StellarMLS April 2026 data.