Key West, FL: Vacation Rental Investment Guide (June 2026)
Conch Republic island escape. Southernmost Florida Keys, 3.5h drive from Miami or direct flights.
The Numbers
Median Price
$1,095,000
ADR
$550
avg daily rate
Occupancy
58%
Proj. Gross Revenue
$116,435
per year · 10.6% gross yield
5-Yr Appreciation
+20%
Property Tax
0.70%
effective / yr
The STR Math
The median Key West deal, run through DSCR math
- Purchase price (median)
- $1,095,000
- Down payment (20%)
- −$219,000
- Loan amount
- $876,000
- P&I @ 7.91% / 30yr
- $6,373/mo
- Property taxes (0.70%/yr)
- $639/mo
- Insurance (~0.9%/yr, elevated for wind/fire/flood)
- $821/mo
- PITIA (full payment)
- $7,833/mo
- Est. STR gross ($550 ADR × 58% occ.)
- $9,703/mo
Illustrative DSCR
1.24
Covers the payment, but below the 1.25 line where the best rate tiers start.
Illustrative only, not a quote or pre-qualification. Uses the June 2026 median price and an ADR × occupancy revenue estimate, an indicative STR rate of 7.91% (10-year Treasury + a typical STR spread — see the live data dashboard), the market's effective tax rate, and estimated insurance bumped for this market's wind/fire/flood exposure. Gross revenue is before cleaning, management, utilities, and platform fees — lenders also haircut projected STR income. Actual numbers vary by property and borrower.
Strategy Check
STR vs long-term rental in Key West
Short-term rental
Wins- Gross income
- $9,703/mo
- Est. PITIA @ 7.91%
- $7,833/mo
- Est. DSCR
- 1.24
Long-term rental
- Lease rent
- $4,800/mo
- Est. PITIA @ 7.53%
- $7,603/mo
- Est. DSCR
- 0.63
Short-term wins on gross by about $4,903/month ($9,703 STR gross vs $4,800 lease rent) — that premium is what pays for furnishing, cleaning, and management, with margin left over if you operate well. Note the fallback: at 0.63 estimated LTR DSCR, lease rent alone doesn't carry the median purchase here — this market's debt wants nightly revenue behind it, so the STR permit picture matters doubly.
Regulation Reality
Can you legally run an STR in Key West?
Transient licenses (required for stays under 28-30 days) have been capped for over a decade — no new ones are issued and existing licenses trade for roughly $250K when available; without one, only monthly-or-longer rentals are legal.
For underwriting, treat nightly-rental revenue as unavailable unless the specific property proves otherwise — a transferable license, grandfathered status, or a location inside an explicitly STR-legal zone. Everything else should be modeled on monthly-or-longer rent (about $4,800/mo here) plus appreciation. That's a different deal — sometimes still a good one — but don't pay an STR price for LTR cash flow.
The Second-Home Angle
Your weekends plus rental income — two ways in
True end-of-the-road island living with year-round warmth and a flight-or-famous-drive arrival — scarcity (ROGO building caps) underpins long-term value.
That dual-use case — your own stays in the weeks you want, rental income the rest of the calendar — is what separates a vacation market from a spreadsheet market, and it opens a second financing door that pure investment properties don't get.
Second-home conventional
As little as 10% down and rates close to a primary residence. The trade: lenders require genuine personal use, qualify you on your own income (W2/DTI), and limit how much of the year the home can be rented out — and some restrict short-term renting entirely. Best when the house is mostly for you and the rental income is offset, not engine.
DSCR investment loan
Typically 20%+ down, priced off the property, and qualified on the property's rental revenue — projected STR income included — rather than your personal income. No personal-use restrictions: rent it 50 weeks, block your own July, run it like the business it is. Best when the income is the point.
Occupancy rules matter: misrepresenting a rental property as a second home is occupancy fraud. If you want unrestricted rental use, the DSCR route exists precisely so you don't have to stretch the truth.
Appreciation & Exit
The hold case in Key West
Key West has appreciated roughly 20% over the past five years — well ahead of typical national pace. That kind of run doesn't repeat on schedule, but it tells you demand for this market survived rate hikes that froze lesser vacation towns. And the supply side is structurally on your side: coastal land doesn't get manufactured, so well-located inventory near the water stays scarce even when demand cools.
Exit liquidity in vacation markets is buyer-pool-dependent: you're selling to the next investor or second-home buyer, both of whom shop with the same seasonality and regulation facts you're reading now. A property with a transferable permit, a documented revenue history, and a real off-season strategy sells like an asset; one without them sells like a house.
Verdict — eyes open
Buyable — eyes open
- —STR regulation is the obstacle, not the revenue: the regime is restricted, so the headline 10.6% gross yield only applies where short-term renting is actually legal.
- —Where short-term renting is permitted, the math itself works — roughly a 1.24 estimated DSCR and 10.6% gross yield on the median deal.
- —The hold case is real regardless: ~20% five-year appreciation in a supply-constrained coastal market.
The viable path: buy a property with the STR license or grandfathered status already attached; underwrite it as a monthly/long-term rental (~$4,800/mo) plus appreciation, not an STR cash machine; or finance it as a second home — 10% down conventional with personal use, renting within your lender's occupancy rules.
Insurance note: Among the most expensive insurance in the US — windstorm via Citizens plus mandatory flood can exceed $20K/yr on a median home.
Seasonality: Winter-spring high season (Dec-Apr) commands huge rates; late summer/early fall is hurricane-season trough with real shutdown risk.
Data as of June 2026 — refreshed periodically. Town-level estimates for screening, not underwriting; verify comps, permits, and insurance quotes on the specific property.
Next Step
Get a quote from an STR expert who lends in Florida
Real pricing on your actual deal — second-home and DSCR routes compared side by side, qualified on the property's income, no hard credit pull to see numbers.
Key West vacation rental FAQ
Is Key West a good place to buy a vacation rental?
Only with eyes open. Transient licenses (required for stays under 28-30 days) have been capped for over a decade — no new ones are issued and existing licenses trade for roughly $250K when available; without one, only monthly-or-longer rentals are legal. The workable angles in Key West: the long-term/monthly rental play (about $4,800/mo), second-home financing with personal use, or buying a property where short-term renting is already legal — not a generic Airbnb purchase (June 2026 data).
Can I make money on Airbnb in Key West?
Where short-term renting is legal, the unit economics are real: a $550 market ADR at 58% occupancy is about $9,703 a month gross. But the restricted regime means most properties can't run nightly rentals at all, so the answer depends entirely on buying the right property. Underwrite the specific address, not the market average.
Can a Key West property double as a second home?
Yes — and the dual-use case is much of the appeal. True end-of-the-road island living with year-round warmth and a flight-or-famous-drive arrival — scarcity (ROGO building caps) underpins long-term value. Two financing routes: a second-home conventional loan (as little as 10% down with owner-occupied-adjacent rates, but lenders impose personal-use and rental-day limits) or a DSCR investment loan (20%+ down, qualifies on the property's rental income, no personal-use restrictions). Given the STR restrictions, the second-home route is arguably the most natural way to own here.
Run the numbers yourself
Calculator
STR calculator — pre-filled for Key West
ADR, occupancy, and median price loaded. Adjust to your deal.
Financing
STR / vacation rental loans, explained
How lenders underwrite projected Airbnb income — and what it costs.
Live Data
Market data dashboard
10Y Treasury, indicative STR rate ranges, and the full leaderboards.
Compare with other vacation markets
Destin, FL
$630,000 median · $440 ADR · 12.7% gross yield
White-sand beach + charter-fishing resort town
Panama City Beach, FL
$385,000 median · $335 ADR · 15.9% gross yield
High-volume family beach + condo strip
Kissimmee, FL
$365,000 median · $245 ADR · 13.7% gross yield
Theme-park vacation-home capital