Islamorada, Florida Short-Term Rental Market
Islamorada STRs averaged $529/night at 59.3% occupancy in April 2026, generating $8,640 average monthly revenue across approximately 9,000 listings.
Quick Answer: Islamorada, 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 Islamorada. Regulations, taxes, and permit details below are specific to Islamorada.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Islamorada is a village in the Florida Keys, marketed as the Sportfishing Capital of the World, with an estimated 1.73 million annual visitors and a permanent population of approximately 7,342 residents. Vacation rental demand is driven by sportfishing, diving, snorkeling, boating, and high-end leisure travel from affluent visitors. The short-term rental market encompasses approximately 8,996 listings by listing type, almost entirely entire-place units (8,844 out of 8,996, or 98%). Private rooms account for 152 listings.
Islamorada is notably VRBO-weighted relative to most STR markets: 2,211 listings appear on VRBO only, 1,508 on Airbnb only, and 5,277 on both platforms. VRBO’s share reflects the vacation-home ownership character of the Keys market, where longer-established rental homes historically used VRBO/HomeAway channels.
The bedroom mix reflects the market’s large-group and upscale orientation: 2-bedrooms lead at 3,504 listings, followed by 3-bedrooms (2,321), 1-bedrooms (1,563), 4-bedrooms (1,056), and 5-bedrooms (538). In April 2026, the market posted a 59.3% average occupancy rate and an average daily rate of $529. RevPAR came in at $314. Year-over-year, occupancy fell 2.6 percentage points while ADR rose 3.5%, yielding a 3.0% revenue gain.
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 under a grandfathered ordinance predating Florida’s 2011 state preemption law, which gives the Village authority to limit the number, location, and operation of vacation rentals. A Village of Islamorada Vacation Rental License is mandatory, costs $1,325 per year, and must be renewed annually for the calendar year. Operators also need a Florida DBPR Chapter 509 state public-lodging license, and a life-safety inspection must pass before initial issuance.
The total village-wide license cap is 331. This is a hard limit and licenses are not transferable on property sale. A new owner must apply for a fresh license, and approval depends on cap availability. In residential zoning, the minimum rental term is 7 days; stays of fewer than 7 nights are only permitted in Tourist Commercial (TC) districts. Rentals of 28 days or more do not require a vacation rental license.
There is no owner-occupancy or primary-residence requirement. Combined lodging taxes total 12.5%: a 5% Monroe County Tourist Development Tax plus a 7.5% Florida sales and use tax. Enforcement is active and strict: the Village uses Rentalscape software to monitor Airbnb, VRBO, and HomeAway listings, combined with GIS mapping and code-compliance officers. Fines and code-enforcement actions are imposed on owners, occupants, and property managers operating without a license.
Market Comparison
Islamorada’s 59.3% occupancy in April 2026 is above the national STR median of approximately 55%, though this masks the severe seasonal variation from 80.2% in February to 40.4% in September. ADR of $529 is more than double the national median of approximately $220, reflecting the premium vacation-destination pricing of the Florida Keys.
Professional property management penetration is high relative to most STR markets, consistent with the Keys’ long history as a professional vacation rental destination. Vacasa leads with 321 listings and 15,979 reviews (rating 4.54). Vacation Rentals of the Florida Keys LLC follows with 232 listings and 4,454 reviews (rating 4.68). Brightwild holds 201 listings and 14,771 reviews (rating 4.64). Last Key manages 156 listings with 8,212 reviews and an exceptional 4.89 rating. Wendy Zintsmaster and Team rounds out the top five with 133 listings and 5,728 reviews (rating 4.81). The top five operators together manage 1,043 listings, roughly 11.6% of the total market, a higher professional concentration than most inland STR markets.
Frequently Asked Questions About Islamorada, Florida
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