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 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
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 | 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 Big Pine Key
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 Big Pine Key?
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
Big Pine Key presents a high-ADR, high-barrier STR investment thesis. The April 2026 average daily rate of $529 across all listings rises to $532 for entire-home units and to $666 for professionally managed properties. Luxury-tier listings average $1,058 per night, indicating significant upside for well-appointed waterfront properties.
At the April 2026 revenue run rate of $8,640 per month, annualized gross revenue is approximately $103,700, against a typical home value of $743,005. That implies a gross revenue yield of roughly 14.0%, which is exceptionally high by national standards but must be discounted against Monroe County’s strict permitting requirements, $490 permit cost, mandatory licensed manager, fire inspection fees, and combined 12.5% transient tax burden.
The median list price of $817,583 reflects a premium for Keys properties already permitted for STR use. Investors should verify parcel-level zoning before purchase: the IS zoning district covers much of Big Pine Key’s residential stock and prohibits short-term rentals outright. Revenue growth scores 87.1 out of 100, the market’s strongest dimension, signaling solid long-term trajectory for compliant operators.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Booking Insights
Big Pine Key bookings average a lead time of 83 days, meaning guests typically reserve nearly three months in advance. This is consistent with a market driven by peak winter season planning, reef diving trips, and multi-night itineraries requiring coordination with boat charters and park permits.
Average length of stay is 4.8 nights, reflecting multi-day nature and dive vacations rather than quick weekend escapes. The combination of long lead times and extended stays creates a predictable booking window: operators can set firm peak-season pricing in October for February and March arrivals with reasonable confidence of filling inventory. Last-minute discounting is less necessary here than in urban STR markets. However, the September trough does produce shorter-notice bookings from budget-conscious divers and local nature tourists, warranting a tiered pricing strategy that opens discounted shoulder-season rates approximately 30 to 45 days out.
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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