Key West, Florida Short-Term Rental Market
Key West, FL STRs averaged $529/night at 59.3% occupancy in April 2026, with one of the most restricted STR supply pools in the US.
Quick Answer: Key West, Florida is an active short-term rental market. average occupancy is 59%. average monthly revenue is $8,640. average daily rate is $529. the top operator is Vacasa with 321 listings. market score is 56/100 (grade C).
Market Score Breakdown
Five dimensions Apivex evaluates per market.
Market Overview
Key West sits at the southernmost point of the continental United States and draws approximately 1 million overnight visitors annually, with 46.5% of all overnight Florida Keys trips concentrated in the city. The STR market is defined by extreme supply constraints: Key West imposed a moratorium on new transient rental licenses (rentals under 28 days) years ago, freezing the pool of legally permissible STR properties. The only way to legally operate an STR is to purchase a property already holding a grandfathered transient license.
The market recorded a $529 average daily rate in April 2026 at 59.3% occupancy, producing a RevPAR of $314. Year-over-year, occupancy fell 2.6% while ADR rose 3.5% and revenue grew 3.0%.
Entire-place listings dominate at 8,844 of 8,996 total tracked listings. Private rooms account for 152 listings. The bedroom mix skews toward 2-bedroom units (3,504 listings), followed by 3-bedroom (2,321), 1-bedroom (1,563), 4-bedroom (1,056), and 5-bedroom (538). Channel distribution shows substantial dual-platform presence: 5,277 listings appear on both Airbnb and VRBO, 2,211 are VRBO-only, and 1,508 are Airbnb-only. The market’s revenue growth score of 87.1 out of 100 reflects consistent ADR expansion, though the regulation score of 56.9 reflects the challenging permit landscape.
Seasonal Patterns
| Month | Occupancy | ADR | Revenue |
|---|---|---|---|
| Jan | 65% | $389 | $6,371 |
| Feb | 80% | $416 | $7,523 |
| Mar | 78% | $444 | $8,824 |
| Apr | 59% | $421 | $6,800 |
| May | 59% | $379 | $5,898 |
| Jun | 68% | $391 | $6,511 |
| Jul | 68% | $382 | $6,712 |
| Aug | 50% | $357 | $5,016 |
| Sep | 40% | $340 | $3,919 |
| Oct | 52% | $363 | $4,662 |
| Nov | 58% | $389 | $5,340 |
| Dec | 61% | $433 | $6,419 |
Top Short-Term Rental Operators in Key West
Ranked by total active listings. Useful for understanding the competitive landscape.
| # | 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 pricing by property type, tier, and bedroom count.
Revenue by Bedroom Count
| 1 bed | 1,563 |
| 2 bed | 3,504 |
| 3 bed | 2,321 |
| 4 bed | 1,056 |
| 5 bed | 538 |
ADR by Property Tier
| Entire Home | $532 |
| Luxury | $1,058 |
| Professionally Managed | $666 |
Revenue by Dwelling Type
| Apartment | $8,163 |
| Entire Place | $8,688 |
| House | $9,409 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 16.8% |
| vrbo | 24.6% |
| both | 58.7% |
Investment Analysis
Key West represents a high-yield, high-barrier STR market. The typical home value is $1,026,000 as of April 2026, with a median sale price of $1,138,000 and a median list price of $1,312,000. Homes take a median of 114 days to go under contract, and the sale-to-list ratio is 0.868, indicating a buyer’s market relative to list prices.
Annualized revenue at the April 2026 run rate is approximately $103,683 per listing ($8,640 per month times 12). Against a typical home value of $1,026,000, that implies a gross yield of roughly 10.1% before expenses and the 12.5% combined lodging tax. This is exceptional for a market in this price tier.
ADR tiers show wide differentiation: all-listing average is $529, entire-home listings average $532, professionally managed properties average $666 (a 26% premium), and the luxury tier reaches $1,058 per night. Revenue by listing type: houses average $9,409 per month, entire-place listings average $8,688, and apartments average $8,163. The narrow gap between listing types reflects the relatively uniform premium pricing across the Key West market.
The 2025 full-year average was $7,470 per month ($89,640 annualized) at 61.0% occupancy and $465 ADR. The premium attached to licensed properties reflects the supply moratorium. Market participants report that licensed properties trade at $400,000 to $500,000 above comparable non-licensed properties, which must be factored into investment underwriting.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Booking Insights
Key West STR bookings average a lead time of 83 days, the longest of any market in this batch and reflecting the behavior of guests who plan winter or spring getaways well in advance. The destination’s unique regulatory constraints also contribute to the extended lead time: with limited licensed inventory, desirable properties fill quickly for peak winter weeks.
Average length of stay is 4.8 nights, above the national STR median and consistent with Key West’s positioning as a destination vacation rather than a weekend trip. At 4.8 nights average and 59.3% April occupancy, a property typically handles five to six guest stays per month. The extended stay length also means fewer cleaning turnovers per booking period, which matters operationally in a market where cleaning and property maintenance costs are elevated.
Operators should implement aggressive dynamic pricing in January through March and secure deposits at booking for the high season. With 83-day average lead time, revenue management tools that adjust pricing 60 to 90 days out are well matched to this market’s booking behavior.
Short-Term Rental Regulations
Key West operates one of the most restrictive short-term rental regimes in the United States. The city imposed a complete moratorium on new transient rental licenses (defined as rentals under 28 days) and has since frozen new supply. Purchasing a property with a grandfathered transient license is the only legal path to operating an STR within Key West city limits.
Existing licensees must maintain a layered permitting stack: a City of Key West Business Tax Receipt (approximately $118 to $300 per year), a designated Vacation Rental Manager License ($110 per year), a Monroe County Business Tax Receipt, a State of Florida DBPR public lodging registration, and an annual Fire and Life Safety Inspection by the Fire Marshal ($100 to $300 depending on unit size). There is no cap on rental nights per year for licensed properties, but the moratorium makes new entry effectively impossible.
A significant supply reduction occurred in December 2025: approximately 300 Truman Annex properties held special transient licenses that expired December 22, 2025 under a 2005 settlement agreement. These properties lost short-term rental rights and may now only rent long-term (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. This is the largest single reduction in the already severely constrained licensed supply pool.
Total lodging tax burden is 12.5% (7.5% Florida state sales tax plus 5% Monroe County Tourist Development Tax). Airbnb auto-collects and remits both taxes; VRBO hosts must remit the Monroe County portion independently. Enforcement is strict: code officers monitor platforms and conduct undercover inspections, with fines up to $5,000 per day, with each day treated as a separate offense.
Market Comparison
Key West’s $529 ADR is more than double the US STR median of approximately $220, reflecting the island’s unique destination status, severe supply constraints, and high per-night pricing power. At 59.3% April occupancy, the market closely tracks the US annual median of approximately 55% in a shoulder month, with winter months pushing well above that.
The revenue growth score of 87.1 is the highest metric in the market’s scorecard, reflecting consistent ADR expansion over the past several years. The regulation score of 56.9 accurately reflects the market’s complex and restrictive permitting framework, which creates barriers to entry that protect existing operators’ yield.
Vacasa leads the Key West operator landscape with 321 listings and 15,979 reviews at a 4.54 average rating. Vacation Rentals of the Florida Keys LLC holds 232 listings with 4,454 reviews at 4.68. Brightwild manages 201 listings with 14,771 reviews at 4.64. Last Key has 156 listings and an exceptional 4.89 average rating from 8,212 reviews. Wendy Zintsmaster and Team rounds out the top five with 133 listings and a 4.81 rating. The top five collectively manage 1,043 listings in a market where the total licensed pool is severely limited.
Frequently Asked Questions About Key West, Florida
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