Big Pine Key, Florida Short-Term Rental Market
Zoning limits Big Pine Key rentals, and Florida Keys September 2026 posted $426 ADR, 39.5% occupancy, $4,942 monthly revenue.
Quick Answer: Big Pine 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 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
This profile covers Big Pine Key, Florida, using data through September 2026. The performance figures come from a shared series that also covers other Florida Keys markets, so every number below describes the Florida Keys STR market rather than Big Pine Key alone. Big Pine Key sits in the Lower Keys, has a population of 4,258, and draws visitors to the National Key Deer Refuge, Looe Key Reef and nearby Bahia Honda State Park. 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. Compared with September 2025, occupancy rose 7.0%, ADR rose 6.7% and revenue rose 10.1%. September is the seasonal low, so these are off-season results. Entire homes averaged $431 per night, while the all-listings average of $426 includes private rooms. Annualized revenue based on the seasonal sum of monthly averages is $74,824. Over the long run the market has moved up: average monthly revenue per listing was $3,280 in 2017, reached $7,250 in 2022, and stood at $7,506 in 2025. The first nine months of 2026 show occupancy of 62.5%, ADR of $493 and average monthly revenue of $8,193. Bedroom, channel and listing-type counts are tracked at a shared regional level rather than uniquely for Big Pine Key, so this profile omits them. The most important feature of this market for buyers is regulatory. Monroe County allows nightly rentals only in certain zoning districts, and a large share of Big Pine Key residential parcels sit in districts where they are banned. Any investment case should start with parcel-level zoning verification, then move to the performance figures.
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 is in unincorporated Monroe County, which runs a strict short-term rental regime. Short-term rentals are permitted, but any rental under 28 days requires a Monroe County Special Vacation Rental Permit, renewed annually. The initial application costs $490 and renewal costs $100. Operators also need a Monroe County Business Tax Receipt, a Florida DBPR public lodging license and a Florida DOR sales tax registration, plus a licensed vacation rental manager on call 24/7 ($110 manager license fee). A fire and life-safety inspection is required at application and at each renewal, from $125 for a 1-bedroom up to $400 for 4 or more bedrooms. The biggest constraint is zoning. Nightly rentals are allowed only in SR, MU, UR, IS-V and OS districts and are expressly prohibited in IS, URM and IS-M districts. A large share of Big Pine Key residential parcels are zoned IS, so most detached houses cannot legally operate as short-term rentals without rezoning. There is no owner-occupancy or primary-residence requirement. The combined transient tax is 12.5%, made up of the 5% Monroe County Tourist Development Tax and 7.5% state and local sales tax, remitted monthly. Enforcement is rated strict. Staff monitor listing platforms, a fraud hotline operates, and a Special Magistrate can issue fines, place liens and revoke permits. Florida’s SB280 preemption bill was vetoed in 2024, which preserved the county’s grandfathered ordinance. The county updated its permit application form in October 2025.
Market Comparison
In September 2026 the Florida Keys STR market posted an ADR of $426 and occupancy of 39.5%. That occupancy figure reflects September, the weakest month of the year. Over the full seasonal cycle, monthly occupancy ranges from 40.3% to 80.2%, and nine of twelve months are above 55%. Average monthly revenue of $4,942 in September and a seasonal-sum annual figure of $74,824 show that the Keys earn strong revenue per listing despite the slow late summer. Year-over-year growth is positive on all three measures, with occupancy up 7.0%, ADR up 6.7% and revenue up 10.1%. The market also has a high entry cost, with a typical home value of $750,647. Top operators are tracked at a shared regional level rather than uniquely for Big Pine Key, so this profile omits them. The Keys reward careful zoning and permit checks, since the regulatory barrier is high.
Frequently Asked Questions About Big Pine Key, Florida
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