Key West, FL
Southernmost point - premium year-round island STR
Key West is America's southernmost city and one of the most supply-constrained STR markets in the US. The island's physical size limits new construction, the Conch Republic culture drives intense brand loyalty, and the tropical climate supports year-round demand. STR regulations are among the most complex in Florida - licensing, registration, and inspection requirements apply.
40 active listings in Key West are analyzed and ranked right now
Scored 1-10 against real Airbnb comps. See which properties rank highest and why.
Estimated Annual Performance
* Estimates based on market averages. Individual property performance varies. Always run a full underwriting analysis.
Why Investors Choose Key West
Key West STR investing, answered
Is Key West, FL a good short-term rental market?
Key West is a Southeast STR market averaging a 2.6% cap rate, 57% annual occupancy, and $378/night across STR-viable listings, based on 40 active listings. Key West is America's southernmost city and one of the most supply-constrained STR markets in the US. The island's physical size limits new construction, the Conch Republic culture drives intense brand loyalty, and the tropical climate supports year-round demand. STR regulations are among the most complex in Florida - licensing, registration, and inspection requirements apply.
What is the average Airbnb occupancy rate in Key West?
STR-viable properties in Key West average about 57% occupancy across the year. Peak season is Year-round (peaks: Fantasy Fest Oct, spring break). Occupancy here reflects availability-adjusted booking performance, not raw calendar occupancy, so it represents what a full-time operated rental can realistically achieve.
How much do short-term rentals earn in Key West?
At $378/night and 57% occupancy, a typical Key West STR grosses roughly $78,643 per year before expenses, leaving an estimated $47,186 in net operating income against a $3.2M average price, an implied 1.5% cap rate. Individual results depend on property, amenities, and management.
What types of properties work best for STR in Key West?
The strongest-performing STR property types in Key West are Conch House, Cottage, Condo, Duplex. Supply-constrained island market - limited new inventory possible. Matching the local guest profile and the amenities that drive bookings in this market matters more than raw square footage.
What is the median STR-viable home price in Key West?
STR-viable listings in Key West average around $3.2M. Primary STR ZIP codes include 33040, 33042. Combined with the market's 2.6% average cap rate, that price level sets the return baseline you'd underwrite against.
Market averages, not guarantees. Cap rates, occupancy, and nightly rates are market-wide averages based on active STR listings and historical data. Individual property performance depends on location, amenities, management, and listing quality. Always run a full underwriting analysis before purchasing.Stats sourced from 40 active listings · last updated Sep 1, 2026
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