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Is Airbnb legal in Key West, Florida?

New investor whole-home rentals effectively banned. Key West froze new transient rental licenses in 2002. Only about 850 transferable licenses exist, and they trade privately at high prices. Without one, the minimum legal rental in a residential home is 28 days. Renting to tourists for less than 28 days without a transient license is a city crime carrying up to 60 days in jail and $5,000 in fines per violation.

Showing the researched rules for Key West, FL below. Type your Key West address to jump to the verdict.

Not allowed

New investor whole-home rentals effectively banned

Key West froze new transient rental licenses in 2002. Only about 850 transferable licenses exist, and they trade privately at high prices. Without one, the minimum legal rental in a residential home is 28 days. Renting to tourists for less than 28 days without a transient license is a city crime carrying up to 60 days in jail and $5,000 in fines per violation.

Permit and costs

Permit
Transient Rental License
Issued by
City of Key West
Cost
Not issued to new applicants, only existing transferable licenses
Renewal
N/A

Key limits

Night cap
Effectively banned without a transferable license
Minimum stay
28 days for homes without a transient license
License supply
Capped since 2002, roughly 850 exist and they are bought and sold
Enforcement
Dedicated code officer, jail time and $5,000 fines per violation

Taxes

State sales tax
6%
County tourist tax
Set by Monroe County, check the current rate

Registration checklist

  1. 1
    Do not buy without a license
    A whole-home STR only works if the property already holds one of the ~850 transferable transient licenses.
  2. 2
    Verify the license transfers
    Confirm with the city that the specific property's transient license transfers with the sale before closing.
  3. 3
    Consider monthly rentals
    Without a transient license, the legal floor is a 28-day minimum, which means a furnished monthly model instead.

What could change this verdict

Your HOA
Condo associations add their own rental rules on top of the city freeze.
County differs
Unincorporated Monroe County runs a separate Special Vacation Rental Permit system with its own strict rules.

Sources

Key West The Newspaper, transient license reporting · Key West Chamber transient rental license info

Rules researched October 2026. They change, so verify with the city before you buy.

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Verify before you buy. Rules change often and vary by zoning, HOA, and building type. This is a research starting point, not legal advice. Always confirm with the city's planning or business-license office before signing anything.