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 is 64%. average monthly revenue is $8,168. average daily rate is $485. the top operator 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 Apivex 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 | ADR | Revenue |
|---|---|---|---|
| Jan | 65% | $391 | $6,388 |
| Feb | 80% | $417 | $7,543 |
| Mar | 78% | $444 | $8,832 |
| Apr | 59% | $421 | $6,803 |
| May | 59% | $391 | $6,080 |
| Jun | 68% | $401 | $6,695 |
| Jul | 68% | $383 | $6,719 |
| Aug | 50% | $357 | $5,021 |
| Sep | 40% | $340 | $3,924 |
| Oct | 52% | $364 | $4,669 |
| Nov | 58% | $390 | $5,347 |
| Dec | 61% | $434 | $6,427 |
Top Short-Term Rental Operators in Islamorada
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 Islamorada?
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 | $488 |
| Luxury | $952 |
| Professionally Managed | $576 |
Revenue by Dwelling Type
| Apartment | $6,387 |
| Entire Place | $8,235 |
| House | $9,605 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 16.8% |
| vrbo | 24.6% |
| both | 58.7% |
Investment Analysis
Islamorada is a high-revenue, high-entry-cost STR market with meaningful regulatory constraints that directly affect investability. The typical home value was $1,225,482 as of April 2026. Median list price was $1,538,333 and for-sale inventory was just 181 properties, with a median days-to-pending of 168 days, indicating a slow-moving, illiquid market with limited buyer competition at these price points.
At $8,640 average monthly revenue in April 2026, the all-listing gross yield at current typical home values is approximately 8.5% annualized (annualized revenue of $103,683 divided by typical home value of $1,225,482). House listings averaged $9,409 per month, projecting to approximately $112,908 annualized, which at the typical home value implies a gross yield near 9.2%. Professionally managed properties commanded $666 per night versus $529 for all listings, a 25.9% premium, and luxury-tier properties averaged $1,058 per night, double the market average.
The critical investment constraint is the 331-license village cap on vacation rental licenses. With a finite supply of legal STR licenses and licenses that are not transferable on sale, buyers must apply for a new license upon purchase rather than inheriting an existing one. A property’s historical revenue may not persist if the new owner’s license application is affected by cap availability or village discretion. Verify current license availability with the Village of Islamorada before acquisition.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Booking Insights
Islamorada has the longest booking lead time of any market in this analysis: guests book 83 days in advance on average, nearly three months before check-in. This reflects the premium nature of the destination and the planning required for expensive Keys vacations. Hosts have an extended revenue management window to adjust pricing, minimum stays, and availability restrictions well ahead of arrival.
With an 83-day average lead time, hosts should set premium pricing for the February-March peak season at least four to six months in advance, as early bookers in high-demand markets typically lock in rates before competitive pricing pressure pushes them higher. Average length of stay is 4.8 nights, consistent with an extended vacation itinerary. A 7-night minimum stay requirement in residential zones (per village ordinance) means many hosts are not seeing the 4.8-night average at all: their actual guest stays in residential zones must be 7 nights or longer, and the 4.8 figure may be dragged down by Tourist Commercial properties where nightly minimums apply.
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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