Big Pine Key, Florida Short-Term Rental Market
Big Pine Key STRs averaged $529/night at 59.3% occupancy in April 2026, with annual revenue up 3% year-over-year.
Quick Answer: Big Pine Key, Florida is an active short-term rental market. average occupancy in the Key West market area is 64%. average monthly revenue in the Key West market area is $8,168. average daily rate in the Key West market area is $485. 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 Key West regional market, which includes Big Pine Key. Regulations, taxes, and permit details below are specific to Big Pine Key.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Big Pine Key operates within one of Florida’s most tightly regulated short-term rental environments, producing a market shaped more by scarcity and compliance barriers than raw volume. As of April 2026, the market recorded an average daily rate of $529, average occupancy of 59.3%, and RevPAR of $314 across active listings. Year-over-year, occupancy slipped 2.6 percentage points while ADR rose 3.5%, resulting in a net revenue gain of 3.0% compared to April 2025.
The market is dominated by entire-place rentals: 8,844 of the roughly 8,996 tracked listings are entire-place units, with just 152 private rooms. By bedroom count, 2-bedroom units lead at 3,504 listings, followed by 3-bedroom (2,321), 1-bedroom (1,563), 4-bedroom (1,056), and 5-bedroom (538). Channel distribution skews toward multi-platform operators: 5,277 listings appear on both Airbnb and VRBO, 2,211 on VRBO only, and 1,508 on Airbnb only. The market score stands at 56.4 overall, with revenue growth rated 87.1 out of 100 and investability at 68.6, reflecting the market’s high revenue potential offset by regulatory complexity and moderate seasonality risk.
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 Big Pine 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 Big Pine Key, so these counts are not Big Pine Key-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 Big Pine Key?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Big Pine 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 | 58.7% |
Home Value Trends (Big Pine Key)
Typical home values, median sale prices, and the 10-year price trend for Big Pine 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 Big Pine 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
Big Pine Key falls under unincorporated Monroe County, which maintains one of Florida’s most restrictive STR frameworks under a grandfathered pre-2011 local ordinance. Short-term rentals (rentals under 28 days) require a Monroe County Special Vacation Rental Permit at $490 for initial application and $100 for annual renewal. A licensed vacation rental manager available 24/7 is mandatory, and operators must also hold a Monroe County Business Tax Receipt, a Florida DBPR public lodging license, and a Florida DOR sales tax registration.
A fire and life-safety inspection is required at initial application and each renewal ($125 for 1-bedroom up to $400 for 4-bedroom or larger). STRs are permitted only in SR, MU, UR, IS-V, and OS zoning districts. They are banned in IS, URM, and IS-M zones, which cover a large share of Big Pine Key residential parcels. Occupancy tax is 12.5% combined (5% Monroe County TDT plus 7.5% state and local sales tax). Enforcement is rated strict: Monroe County actively monitors platforms, operates a violations hotline, and refers violations to a Special Magistrate who can issue fines, liens, and permit revocations.
A 2024 statewide preemption bill was vetoed, preserving Monroe County’s authority. Monroe County updated its permit application form in October 2025. Investors must verify parcel-level zoning before purchase.
Market Comparison
Big Pine Key’s April 2026 ADR of $529 is more than double the US STR median ADR of approximately $220, placing it among the top-tier coastal markets nationally. Occupancy at 59.3% runs slightly above the US median of approximately 55%, a notable result given the market’s strict permitting environment that limits supply.
The professionally managed premium is significant: PM-tier listings average $666/night versus $529 overall, a 26% uplift. Vacasa leads the market with 321 listings and 15,979 reviews (4.54 average rating). Vacation Rentals of the Florida Keys follows with 232 listings and 4,454 reviews (4.68 rating). Brightwild holds 201 listings with 14,771 reviews (4.64 rating). Last Key manages 156 listings at a 4.89 rating, the highest among the top five. Wendy Zintsmaster and Team rounds out the top five with 133 listings and a 4.81 rating.
Market score regulation stands at 56.9 out of 100, reflecting the compliance overhead. Revenue growth at 87.1 out of 100 is the standout metric, suggesting that operators who successfully navigate permitting can expect above-average long-term revenue trajectory.
Frequently Asked Questions About Big Pine Key, Florida
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