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Florida · Key West

Key West

city Restricted Needs review · last verified 2026-07-02

Transient (vacation) rentals under 30 days are legal in Key West ONLY in a handful of non-residential zoning districts (HRCC-1, HRCC-3, HCT, HNC-1, HNC-3) AND only with a City Business Tax Receipt, an active State of Florida (DBPR) vacation-rental license, and the City's transient rental license/medallion. The City maintains a cap on new transient licenses, so existing licenses are effectively grandfathered and, per the City, converting a residential property to transient use is "very difficult, if not impossible." Residential rentals of 29+ days are non-transient and broadly allowed with a City Business Tax Receipt.

Not legal advice. Last verified 2026-07-02 · sources linked below.

Requirements checklist

  • state Florida DBPR Vacation Rental License Required
    Fee: $170 / annual · Renewal: Annual (staggered by DBPR district) · Applies to: Any entire dwelling/dwelling unit or condo rented to guests more than 3 times in a calendar year for periods of less than 30 days / 1 calendar month, or advertised as such. · official page ↗
  • city City of Key West Business Tax Receipt (BTR) Required
    Fee: — · Renewal: Annual · Applies to: All residential rental properties in the City of Key West, both non-transient (29+ days) and transient (28 days or less). · official page ↗
  • city City Transient Rental License / Medallion (Regulatory License supporting the BTR) Required
    Fee: — · Renewal: Annual · Applies to: Each dwelling unit rented transiently (less than 30 days). Only obtainable where the property is in a zoning district that allows transient use (HRCC-1, HRCC-3, HCT, HNC-1, HNC-3) and subject to the City's cap on new transient licenses. · official page ↗
  • city Designated Local Vacation Rental Manager Unknown
    Fee: — · Renewal: — · Applies to: Transient/vacation rental units are generally required to designate a local responsible manager, but a distinct City-issued 'special vacation rental manager license' could NOT be confirmed firsthand on an official City page in this pass. · official page ↗
  • county Monroe County Tourist Development Tax Account + Local Business Tax Receipt Required
    Fee: — · Renewal: Annual (business tax receipt) · Applies to: All rental properties in Monroe County must obtain a local business tax receipt; rentals of 6 months or less must also open a Tourist Development Tax account with the Monroe County Tax Collector. · official page ↗

Taxes

TaxRateAdministered byAirbnb remitsVrbo remits
Florida State Sales Tax (Transient Rentals) 6% Florida Department of Revenue (DOR) Yes No
Monroe County Discretionary Sales Surtax 1.5% Florida Department of Revenue (DOR) Yes No
Monroe County Tourist Development Tax (TDT) 5% Monroe County Tax Collector (self-administered / locally administered) No No

Operating rules

Primary residence
—
Min stay (nights)
30
Max nights / year
—
Max occupancy
Occupancy, off-street parking, and density (units-per-acre) standards are governed by Chapter 122 (Zoning); specific per-unit occupancy caps not confirmed verbatim in this pass.
Zoning-restricted
Yes
Cap on licenses
Yes

Grandfathering: The City maintains a cap on new transient (vacation rental) licenses; existing licensed transient properties are effectively grandfathered. New transient licenses in residential districts are not being issued, making conversion of residential property to transient use, per the City, 'very difficult, if not impossible.' Consistent with Fla. Stat. 509.032(7)(b), whose duration/frequency preemption 'does not apply to any local law, ordinance, or regulation adopted on or before June 1, 2011.'

Zoning: Transient use (rentals of less than 30 days) is permitted only in zoning districts HRCC-1, HRCC-3, HCT, HNC-1 and HNC-3. In HNC-1 and HNC-3, redevelopment/conversion of permanent housing to transient use is permitted only if no on-site reduction of permanent housing occurs. Residential rentals of 29+ days (non-transient) are broadly allowed with a City Business Tax Receipt.

  • Non-transient residential rentals: 'may not be rented for less than 29 days at a time'; transient = '28 days or less'. Under 30 days triggers the state DBPR vacation-rental license and City transient/vacation-rental requirements.
  • The City itself warns: 'The City has very few zoning districts in the historic district which allow transient use, and the City has very strict off-street parking and density (units-per-acre) requirements. These restrictions coupled with a current cap on new transient licenses makes it very difficult, if not impossible, to convert a residential property to transient use.'

Enforcement

Active enforcement
high
Fines
Reported penalties for operating an illegal transient rental include fines up to $5,000 per violation and up to 60 days imprisonment, with each day of unauthorized operation a separate violation. These specific dollar/jail figures come from a secondary aggregator (The Offer Sheet) and could NOT be confirmed firsthand against the City code in this pass; the underlying penalty structure derives from Chapter 122 code enforcement. Treat as unverified.
Notes
The City actively maintains and publishes a list/map of licensed transient rental properties (cityofkeywest-fl.gov/856) so the public can verify licensure before booking. The scarcity of transient licenses (capped, grandfathered) drives strong enforcement against unlicensed operations. Exact fine schedule should be verified against Chapter 122 and the City's code enforcement provisions.

Official sources

Informational summary of publicly available sources; not legal advice. Verify against the linked official sources.