Short-term rental rules · Key West, Florida
Short-term rentals in Key West, explained properly.
Key West splits residential rentals into two categories: non-transient rentals, which may not be rented for less than 29 days at a time, and transient rentals of 28 days or less, which require a transient rental license. The city stopped issuing new transient licenses years ago and grandfathered the existing ones, so legal nightly or weekly rentals depend on a property already holding one of a limited pool of licenses — which transfer with the property and trade on a secondary market for as much as $400,000. Every rental also needs a City of Key West Business Tax Receipt and a Florida DBPR license, and Monroe County's tourist development tax applies on top of state sales tax.
Draft. These rules were compiled from the sources listed below — official where available, with fields that rely on secondary sources marked for review — and have not yet been checked line by line. Confirm with the city before making decisions.
At a glance
What you need to know before you buy or list
| Question | Answer |
|---|---|
| Transient = 28 days or less; non-transient = 29+ days | Non-transient residential rentals may not be rented for less than 29 days at a time; rentals of 28 days or less are transient and require a transient rental license[1] |
| No new transient licenses; existing ones grandfathered | The city stopped issuing transient rental licenses and grandfathered those already in existence, so the supply of legal short-term rental units is effectively fixed; the exact adoption date and ordinance number were not confirmed in this pass[2]Confirming |
| Licenses transfer and trade for up to $400,000 | Transient licenses can be transferred, and homes holding them carry a premium; a local brokerage reports secondary-market license prices of as much as $400,000[2]Confirming |
| City Business Tax Receipt and Florida license required | All residential rental properties need a City of Key West Business Tax Receipt; transient rentals also require a State of Florida license as part of the application. Business tax amounts are set in City Code Section 66-109[1] |
| City urges renters to verify licenses | The city recommends renters confirm a vacation rental's license with the Licensing Division before sending payment[1] |
| Monroe County 5% tourist tax plus state sales tax | A secondary source puts the Monroe County Tourist Development Tax at 5% and Florida sales tax (with local surtax) at 6.5% in Monroe County, roughly 11.5% combined; not confirmed against an official rate schedule[3]Confirming |
| Fines reported up to $5,000 per violation | A secondary source reports a written warning or fine up to $500 for a first violation and $1,000 to $5,000 per subsequent violation, plus platform delisting on city notice; not confirmed against the city code[3]Confirming |
| Last researched | September 25, 2026 |
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Detailed rules
The full picture, section by section
Florida statewide framework
| Key West's rules rely on Florida's pre-2011 grandfather clause | Florida Statutes 509.032(7) bars local governments from prohibiting vacation rentals or regulating stay length unless their ordinance was in place by June 1, 2011; Key West's transient-rental restrictions predate that cutoff. A 2024 bill that would have changed the framework was vetoed[4]Confirming |
|---|
Changes
Recent and pending changes
Watch the City of Key West licensing FAQ and City Commission agendas. The license freeze date, ordinance number, current business-tax amount for transient units, and penalty schedule were not confirmed from official sources in this pass. Any state change to the pre-2011 grandfather clause would directly affect Key West's ability to restrict transient rentals.
Sources
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This page is general information compiled from public sources, not legal or tax advice. HOA rules, deed restrictions and zoning for a specific property can be stricter. Confirm with the local permitting office and a qualified professional before buying or listing a property.