Is short-term rental legal in Key West, FL?
Key West licenses transient rentals tightly: a transient rental license is required, licenses are limited and many are tied to specific properties/areas from older allocations — in much of the island, the license exists or it doesn't, and no new application changes that.
Rules checked October 2026
Run the Key West verdict on your facts
| What counts as a short-term rental | Key West licenses transient rentals tightly: a transient rental license is required, licenses are limited and many are tied to specific properties/areas from older allocations — in much of the island, the license exists or it doesn't, and no new application changes that. |
|---|---|
| Permit / license | Transient Rental License (limited stock) — issued by City of Key West |
| Fee | License and transfer costs vary — the scarcity is the price |
| Renewal | Annual business tax/licence renewals |
| Primary-residence rule | No primary-residence rule; license scarcity governs. |
| Whole-home rental | Whole-home rental under a valid transient license; without one, rentals under 26 days are not lawful in most districts. |
| Night cap | — |
| Guests / occupancy | Per license |
| Minimum stay | Transient = under 26 days in Key West's code |
| Zoning | License availability by district is the map; Old Town rules are their own subspecies. |
| Density / scarcity | Transient rental licenses are a limited, largely closed stock |
| Fines | Unlicensed transient rentals draw city fines and Monroe County/state consequences; enforcement is a standing island industry |
| Taxes | State DBPR + Monroe County tourist taxes accompany licensed operation. |
| Platform duties | Listings are checked against the license roll. |
| State layer | § 509.032(7), Fla. Stat.: a local law may not prohibit vacation rentals or regulate their duration or frequency — EXCEPT ordinances adopted on or before June 1, 2011, which survive in full. That grandfather clause is why Miami Beach-style bans persist a few miles from cities that cannot ban at all. A state DBPR vacation-rental license and local business tax receipt / registration still apply on top. |
What trips hosts in Key West
- Key West's transient licenses behave like medallions: they price into property values and invite fraudulent claims. Verification with the city is the whole game.
The private layer still applies
These are the city's rules. Your HOA, condo board, lease or mortgage can say no on top of them — that layer is printed as a warning in the checker, never merged into the city's verdict.
Sources: Key West Code of Ordinances (transient rental licensing) · City of Key West licensing program. Rules checked October 2026.