Key West, Florida Short-Term Rental Market
Key West has a license moratorium, and Florida Keys September 2026 STR averaged $426 ADR, 39.5% occupancy, $4,942 monthly revenue.
Quick Answer: Key West, 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 321 listings. market score is 56/100 (grade C).
Market data reflects the wider Key West market, which covers 8 areas. Regulations, taxes, and permit details below are specific to Key West.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Key West has a moratorium on new transient rental licenses, so only grandfathered properties can operate legally. Performance figures on this page describe the Florida Keys STR market, which Key West shares with Big Pine Key, Key Colony Beach, Islamorada and Key Largo. Regulations and home values describe Key West itself. In September 2026 the Florida Keys STR market averaged an ADR of $426 and occupancy of 39.5%, producing average monthly revenue of $4,942 per listing. Entire home ADR was $431. Compared with September 2025, occupancy rose 7.0%, ADR rose 6.7% and revenue rose 10.1%. September is also the weakest month in the seasonal data, where it averages 40.3% occupancy, so the current reading reflects the low point of the calendar. Across the first nine months of 2026, occupancy averaged 62.5%, ADR $493 and monthly revenue $8,193, compared with 60.9%, $468 and $7,506 for full year 2025. Occupancy peaked at 71.4% in 2021 and has held near 60% in 2024 and 2025, while ADR climbed from $331 in 2020 to $493 in 2026 year to date. Summing the twelve seasonal months gives annualized revenue of $74,824. Demand is tied to visitor volume. Key West draws about 1 million visitors a year and captures 46.5% of overnight Florida Keys trips. About 87% of visitors are domestic, and roughly 30% of visiting households earn over $150,000. The island also recorded 512,800 cruise passengers in 2024, along with more than 813,000 airport arrivals and 93,665 ferry passengers. Average per-person trip spending was $1,667 in 2023, with lodging about 47% of it. Bedroom mix, channel mix, listing-type counts and top operators are tracked at a shared regional level rather than uniquely for Key West, so this profile omits them. Data month: September 2026.
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 Key West 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 Key West, so these counts are not Key West-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Vacasa | 321 | 15,979 | ★ 4.54 |
| 2 | Vacation Rentals of the Florida Keys LLC. | 232 | 4,454 | ★ 4.68 |
| 3 | Brightwild | 201 | 14,771 | ★ 4.64 |
| 4 | Last Key | 156 | 8,212 | ★ 4.89 |
| 5 | Wendy Zintsmaster and Team | 133 | 5,728 | ★ 4.81 |
What Kind of STR Should I Buy in Key West?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Key West 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 | 58.7% |
Home Value Trends (Key West)
Typical home values, median sale prices, and the 10-year price trend for Key West 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 Key West — 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
Key West operates one of the most restrictive short-term rental regimes in the United States. The city has a moratorium on new transient rental licenses, which cover rentals under 28 days, and enforcement is rated strict. STRs are permitted, but only for properties that already hold a grandfathered transient license. Transient rentals are prohibited in R-1, R-2 and R-3 residential districts and most residential neighborhoods, and zoning does not override the moratorium. Licensed operators need a City of Key West Business Tax Receipt, a designated Vacation Rental Manager License, a Monroe County Business Tax Receipt, a Florida DBPR public lodging license and an annual Fire and Life Safety Inspection. The listed permit cost is $260, renewed annually. There is no stated cap on nights per year, and neither owner occupancy nor primary residence is required. The total lodging tax is 12.5%, made up of 7.5% Florida state sales tax and 5% Monroe County Tourist Development Tax. Airbnb collects and remits both, while VRBO hosts must remit independently. Violations carry fines of up to $5,000 per day plus up to 60 days imprisonment, with each day treated as a separate offense. The most important recent change is that special Truman Annex transient licenses, about 300 units, expired December 22, 2025 under the 2005 settlement agreement. Those properties may now rent only long term, at 28 days or more. A proposed 20 year extension in exchange for $750,000 per year for affordable housing was rejected by the City Commission. Confirm current rules with the City before buying.
Market Comparison
The Florida Keys market is a high rate, uneven occupancy market. September 2026 occupancy of 39.5% is low, which is expected for the weakest month of the year, where September averages 40.3% in the seasonal data. The September 2026 ADR was $426, and the lowest seasonal ADR is $349 in September. Year to date in 2026, occupancy averages 62.5% and ADR is $493. The seasonal data shows occupancy above 55% in nine of twelve months, with only August, September and October below that line. Monthly revenue of $4,942 in September and $8,193 year to date reflect the rate level. The structural difference from most US markets is supply. Because Key West has frozen new transient licenses and about 300 Truman Annex units lost their rights in December 2025, competition from new entrants is limited, while demand is supported by about 1 million annual visitors. Top operator names are tracked at a shared regional level rather than uniquely for Key West, so this profile omits them.
Frequently Asked Questions About Key West, Florida
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