Islamorada, Florida Short-Term Rental Market
Islamorada caps licenses at 331; Florida Keys STRs averaged $426 ADR, 39.5% occupancy, $4,942 monthly revenue in September 2026.
Quick Answer: Islamorada, 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 Islamorada. Regulations, taxes, and permit details below are specific to Islamorada.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Islamorada sits in the Florida Keys, and the performance figures on this page describe the Florida Keys STR market, a shared regional series rather than numbers measured uniquely for Islamorada. The latest data month is September 2026. In that month 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 a year earlier, occupancy is up 7.0%, ADR is up 6.7% and revenue is up 10.1%. September is the weakest month of the Keys calendar, so this reading reflects the off-season rather than the annual norm. Across the first nine months of 2026 the market has averaged 62.5% occupancy, a $493 ADR and $8,193 in monthly revenue, ahead of full year 2025 at 60.9% occupancy, a $468 ADR and $7,506 in monthly revenue. Seasonal monthly averages sum to $74,824 in annual revenue per listing. Islamorada itself is a village of 7,342 residents with an estimated 1,730,000 annual visitors, a figure derived from its share of Keys overnight trips rather than an official count. It is billed as the Sportfishing Capital of the World. About 55% of 2023 Keys visitors came primarily to relax and escape, while fishing and adventure each drew about 6%. Visitors spend an average of about $1,667 per person per trip, with lodging near 47% of that spend. Local draws include Theater of the Sea, Robbie’s of Islamorada and its tarpon feeding dock, Anne’s Beach and Indian Key Historic State Park. Bedroom, channel and listing-type counts are tracked at a shared regional level rather than uniquely for Islamorada, so this profile omits them.
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 Islamorada 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 Islamorada, so these counts are not Islamorada-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 Islamorada?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Islamorada 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 (Islamorada)
Typical home values, median sale prices, and the 10-year price trend for Islamorada 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 Islamorada — 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
Short-term rentals are legal in Islamorada but tightly controlled, and enforcement is rated strict. The Village operates under a grandfathered ordinance that predates Florida’s June 1, 2011 state preemption, which allows it to limit the number, location and operation of vacation rentals. Total licenses are capped at 331 village-wide, so availability is limited. Operators need a Village of Islamorada Vacation Rental License, which costs $1,325 per year and renews annually for the calendar year, plus a Florida DBPR Chapter 509 state lodging license. A life-safety inspection must be passed before a license is issued. In residential zoning the minimum rental term is 7 days. Stays shorter than 7 days are allowed only in Tourist Commercial districts. Rentals of 28 days or more do not require a vacation rental license. Licenses are not transferable on sale, so new owners must apply fresh. Properties must meet minimum assessed value criteria tied to their Future Land Use designation. There is no owner occupancy or primary residence requirement, and no annual night limit is published. Lodging is taxed at a combined 12.5%, made up of a 5% Monroe County Tourist Development Tax and 7.5% Florida sales and use tax. The Village contracted Rentalscape to monitor Airbnb, VRBO and HomeAway listings, and also uses GIS mapping and code compliance officers. Fines and code enforcement actions apply to owners, occupants and property managers operating without a license. 2026 applications are being accepted through the City View portal.
Market Comparison
The Florida Keys STR market shows a split profile. September 2026 occupancy of 39.5% is the seasonal low, while seasonal averages reach 57.7% in November and 80.2% in February. ADR is the clear advantage. At $426 in September 2026, the market holds strong rates, and even the weakest seasonal ADR, $349 in September, stays high. Luxury listings reach $854. Revenue growth also stands out, with monthly revenue up 10.1% year over year. The tradeoff is price of entry and supply control: a typical Islamorada home is valued at $1,244,163 and the Village caps licenses at 331. Top operators are tracked at a shared regional level rather than uniquely for Islamorada, so this profile omits them. Investors comparing Islamorada with national markets should expect high rates, strong winter demand, a pronounced fall lull and strict compliance requirements.
Frequently Asked Questions About Islamorada, Florida
Are short-term rentals legal in Islamorada?
What is the minimum stay for a rental in Islamorada?
What are average Airbnb rates and occupancy in the Florida Keys market?
When is the best time of year for Islamorada short-term rental revenue?
How much does a home cost in Islamorada?
Can a vacation rental license be transferred to a new owner?
What taxes apply to Islamorada vacation rentals?
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