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.
Across 181 active STR-viable listings analyzed this month, Key West shows a 4.9% median cap rate at a $860K median list price, 47% occupancy, and $414/night. That ranks #11 of 57 markets in STRROI's live ranking. At typical prices the income covers expenses with a moderate margin; deals work best with a solid down payment or a below-market purchase.
Key West real estate market right now
As of October 17, 2026, STRROI is tracking 181 homes for sale in Key West that could run as short-term rentals, at a median list price of $860,000. The middle half are priced between $599K and $1.5M. That works out to a median of $767 per square foot for a typical 1,222 square foot home. Homes here have been on the market 130 days on average, longer than the 101 days typical across the 56 markets in STRROI's ranking, which usually leaves more room to negotiate on price. 52 of them were listed in the last 30 days.
These numbers cover the homes for sale STRROI analyzes as potential short-term rentals in Key West, mainly ZIP 33040. They are not every home sale in the area, so they can differ from MLS-wide figures. Month-by-month price history starts Oct 2026 and fills in as the market is re-checked each month.
What's for sale in Key West right now
Of the 181 homes for sale we analyzed in Key West, 29 (16%) project positive monthly cash flow with 20% down at a 7.5% rate, and 1 rate Buy or better on STRROI's 1-10 scale. 2-bedroom homes are the most common (82 for sale, median $687K). Returns are strongest in 4-bedroom homes at a 5.4% median cap rate, and weakest in 5+ bedroom homes at 4.1%. By property type, manufactured homes lead at a 6.8% median cap rate across 23 listings.
- Buy: 1
- Moderate Buy: 3
- Watch: 3
- Weak: 95
- Avoid: 79
| Beds | For sale | Median price | Cap rate |
|---|---|---|---|
| 1 | 15 | $545K | 5.0% |
| 2 | 82 | $687K | 4.8% |
| 3 | 39 | $999K | 5.1% |
| 4 | 18 | $1.5M | 5.4% |
| 5+ | 26 | $3.0M | 4.1% |
| Type | For sale | Median price | Cap rate |
|---|---|---|---|
| Single-family homes | 41 | $1.2M | 4.2% |
| Townhouses | 41 | $750K | 4.3% |
| Condos | 41 | $639K | 5.0% |
| Multi-family | 35 | $1.7M | 5.1% |
| Manufactured homes | 23 | $439K | 6.8% |
Top-ranked homes for sale in Key West this month
Scored 1-10 against real Airbnb comps. Addresses, photos and the full underwriting are in the app.
- #1Buy · 7/102 bd · 1 ba manufactured homeZIP 33040 · listed at $399K
- Cap rate
- 8.4%
- Cash flow
- +$559/mo
- Nightly
- $352 at 47%
- #2Moderate Buy · 6/104 bd · 3 ba multi-family propertyZIP 33040 · listed at $899K
- Cap rate
- 8.0%
- Cash flow
- +$996/mo
- Nightly
- $364 at 47%
- #3Moderate Buy · 6/103 bd · 2 ba single-family homeZIP 33040 · listed at $749K
- Cap rate
- 7.9%
- Cash flow
- +$747/mo
- Nightly
- $598 at 47%
How Key West compares
Key West ranks #4 of 21 Southeast markets in STRROI's live ranking; St. Augustine leads the region with a median cap rate of 5.7%. Its 4.9% cap rate is 2.0 points above the 2.9% median across all 57 ranked markets, and its $860K typical list price is pricier than the Southeast median of $633K.
| Rank | Market | Cap rate | Typical price |
|---|---|---|---|
| #4 | St. Augustine, FL | 5.7% | $300K |
| #6 | New Orleans, LA | 5.7% | $450K |
| #9 | Savannah, GA | 5.2% | $799K |
| #11 | Key West, FL | 4.9% | $860K |
| #14 | Panama City Beach, FL | 4.4% | $465K |
| #15 | Myrtle Beach, SC | 4.4% | $315K |
| #21 | Gulf Shores, AL | 3.7% | $499K |
Rank is national, by median cap rate across active STR-viable listings. Cash flow uses STRROI's default financing assumptions. See the full ranking
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 with a 4.9% median cap rate, 47% annual occupancy, and $414/night across STR-viable listings, based on 181 active listings. It ranks #11 of 57 markets by median cap rate in STRROI's live ranking. This month 1 of its 181 homes for sale rates Buy or better.
What is the average Airbnb occupancy rate in Key West?
STR-viable properties in Key West average about 47% 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 $414/night and 47% occupancy, a typical Key West STR grosses roughly $71,324 per year before expenses, leaving an estimated $42,794 in net operating income. Across analyzed listings the median cap rate is 4.9%. Individual results depend on property, amenities, and management.
What types of properties work best for STR in Key West?
Among homes for sale right now, 4-bedroom homes post the strongest median cap rate by size (5.4%), and manufactured homes lead by property type (6.8%). With guests, the best-performing STR types here are Conch House, Cottage, Condo, Duplex. Matching the local guest profile and the amenities that drive bookings matters more than raw square footage.
How many homes for sale in Key West cash flow as an Airbnb?
29 of 181 STR-viable listings (16%) project positive monthly cash flow after the mortgage, assuming 20% down at a 7.5% rate on a 30-year loan. The top-ranked listing this month is a 2-bedroom manufactured home in ZIP 33040 listed at $399K, projecting a 8.4% cap rate and +$559 a month.
What is the median home price in Key West, FL right now?
The median list price of the 181 homes for sale STRROI tracks in Key West is $860,000, and the middle half are priced between $599K and $1.5M. The median price per square foot is $767. These are homes that could run as short-term rentals, mainly ZIP 33040, not every sale in the area. Against a 4.9% median cap rate, that price level sets the return baseline you'd underwrite against.
How long do homes stay on the market in Key West?
Homes for sale in Key West have been listed 130 days on average, longer than the 101 days typical across the 56 markets in STRROI's ranking, which usually leaves more room to negotiate on price. 52 of them were listed in the last 30 days.
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 181 active listings · last updated Oct 17, 2026
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