Summerland Key, Florida Short-Term Rental Market
Permit and zoning limit Summerland Key rentals; Florida Keys September 2026 ADR $426, occupancy 39.5%, revenue $4,942.
Quick Answer: Summerland Key, Florida is an active short-term rental market. average occupancy in the Key West market area is 40%. average monthly revenue in the Key West market area is $4,942. average daily rate in the Key West market area is $426. the top operator in the Key West market area is Vacasa with 337 listings. market score is 57/100 (grade C).
Market data reflects the Key West regional market, which includes Summerland Key. Regulations, taxes, and permit details below are specific to Summerland Key.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Summerland Key sits in the Lower Florida Keys in Monroe County, about 20 miles east of Key West. The performance figures on this page describe the Florida Keys STR market rather than Summerland Key alone. In September 2026 the Florida Keys STR market posted an average daily rate of $426 and occupancy of 39.5%, with average monthly revenue of $4,942 per listing. Compared with a year earlier, occupancy rose 7.0%, ADR rose 6.7%, and revenue rose 10.1%. September is the seasonal low point for the region, so the absolute occupancy figure is lower than the annual picture suggests. Year to date through September, 2026 shows occupancy of 62.5%, ADR of $493 and average monthly revenue of $8,193, ahead of the full-year 2025 readings of 60.9%, $469 and $7,511. Entire homes price slightly above the overall average, with an entire-home ADR of $431. The Florida Keys draw visitors from across the state and beyond. Monroe County tourism data shows about 4.45 million overnight visitors in 2023, who stay roughly 5.3 to 6.0 nights and spend about $1,667 per person per trip. Top in-state feeder markets are Miami-Fort Lauderdale, Tampa-St. Petersburg and West Palm Beach, along with New York. Lower Keys visitors are drawn to diving at Looe Key Reef, backcountry and flats fishing, and boating, rather than Key West nightlife. Bedroom, channel and listing-type counts and top operator names are tracked at a shared regional level rather than uniquely for Summerland Key, so this profile omits them. Buyers should treat zoning as the first screen, since many Keys homes cannot legally operate as short-term rentals.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 65% |
| Feb | 80% |
| Mar | 78% |
| Apr | 59% |
| May | 59% |
| Jun | 68% |
| Jul | 68% |
| Aug | 50% |
| Sep | 40% |
| Oct | 52% |
| Nov | 58% |
| Dec | 61% |
Month-by-month nightly rates and revenue figures for Summerland Key are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Key West market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Key West market as a whole, which includes Summerland Key, so these counts are not Summerland Key-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Vacasa | 337 | 21,234 | ★ 4.55 |
| 2 | Vacation Rentals of the Florida Keys LLC. | 232 | 4,472 | ★ 4.68 |
| 3 | Brightwild | 208 | 14,851 | ★ 4.62 |
| 4 | Last Key | 156 | 8,230 | ★ 4.89 |
| 5 | Wendy Zintsmaster and Team | 133 | 5,749 | ★ 4.81 |
What Kind of STR Should I Buy in Summerland Key?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Summerland Key are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 16.8% |
| vrbo | 24.6% |
| both | 58.6% |
Home Value Trends (Summerland Key)
Typical home values, median sale prices, and the 10-year price trend for Summerland Key are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Summerland Key — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Summerland Key falls under Monroe County rules for the unincorporated Florida Keys, which are among the strictest in Florida, and enforcement is rated strict. Short-term rentals are permitted, but only in certain land-use districts. A vacation rental is any stay under 28 days, and those stays are allowed in Suburban Residential, Mixed Use, Urban Residential, Improved Subdivision-Vacation Rental and Offshore Islands districts. They are unlawful in the Improved Subdivision, Urban Residential Mobile Home and IS-M districts, which cover much of the Keys’ residential housing. Gated communities with an HOA that manages vacation rentals may be exempt from the permit. Where rentals are allowed, owners need an annual Monroe County Special Vacation Rental Permit for each dwelling unit, a local Business Tax Receipt, and a licensed vacation rental manager. The permit fee is not published in the data used here. Permits are non-transferable, so a sale voids the permit and the new owner must reapply, including certified-mail notice to property owners within 300 feet at least 30 days before approval. There is no annual night cap, and neither owner occupancy nor primary residence is required. Taxes include a 5% Monroe County Tourist Development Tax, plus Florida sales and use tax of 7.5%. Monroe County application forms were last revised in October 2025, and no loosening of the 28-day rule has been reported. Always verify a parcel’s district with Monroe County Planning and Environmental Resources before buying.
Market Comparison
The Florida Keys STR market is a high-rate, variable-occupancy market. The September 2026 ADR of $426, the $431 entire-home rate and the $518 professionally managed rate show strong pricing. Occupancy runs the other way in the low season, with September’s 39.5% marking the trough of the year. The picture improves across the year, with 2025 occupancy of 60.9% and 2026 year to date at 62.5%. Occupancy in the region was higher in 2021, at 71.3%, and has settled lower since, while ADR has climbed from $389 in 2021 to $493 in 2026 year to date. The market has shifted from volume to rate. Revenue growth is firm, with September revenue up 10.1% year over year. Regulation is the other point of difference: most US markets do not combine annual county permits, district-level bans and strict enforcement. Top operators are tracked at a shared regional level rather than uniquely for Summerland Key, so this profile omits them. Investors who clear the zoning requirement gain access to high nightly rates, but they carry a deeper seasonal trough and higher entry costs.
Frequently Asked Questions About Summerland Key, Florida
Are short-term rentals legal in Summerland Key?
What is the average daily rate in the Florida Keys STR market?
What is the occupancy rate for Summerland Key short-term rentals?
How much revenue does a short-term rental earn in the Florida Keys?
What are the best months for Summerland Key rentals?
What taxes apply to short-term rentals in Summerland Key?
What does a home cost in Summerland Key?
Analyze Summerland Key Rentals
Use our free calculator to estimate Airbnb revenue for any property in Summerland Key.
Free Summerland Key STR Calculator →
