Key West, FL Short-Term Rental Checklist (Free, Printable)

📋 The Basics

Can I rent my place short-term here?: Yes, with a permit
Do I need a permit?: Yes. Short stays (28 days or less) need a city transient license and a Business Tax Receipt.
What taxes do I pay?: Total about 12.5%. Airbnb collects some; you pay Monroe County's 5% tourist tax yourself.

Your 3 steps to be legal

Check that your home can hold a transient license (non-transient homes need stays of 29+ days).
Get a Florida state rental license (DBPR) and sign up for Florida sales tax.
Get the city Business Tax Receipt and transient license, and sign up for Monroe County tourist tax.

⚠️ Biggest risk: Renting for under 29 days without a transient license.

Words confusing? See the glossary. Details and official sources are below.

This is the general rule for Key West. Does your address qualify?

The free info covers the city as a whole. Your property can still be different: zoning can change from one street to the next, and an HOA or condo ban can stop rentals even where the city allows them.

Your $49 Compliance Check looks at your exact property:

Whether your exact address and zone allow short-term rentals
A check of HOA / condo rental restrictions to look for
Which permits and tax accounts you personally need
What you're missing right now
A personal report with clear next steps and official sources, by email
A refund if we report a rule in error (refund policy)

🔎 How we check: official city, county and state sources, a last-verified date on every page, and nothing guessed. Learn more

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Permit / license / registration

State license (Florida DBPR): Florida DBPR vacation rental / transient public lodging license (homestead room-rental exemptions may apply).
Categories: Transient = 28 days or less; non-transient rentals may not be rented for less than 29 days.
Registration: All residential rentals need a City of Key West Business Tax Receipt; transient use requires a city transient license (Code Ch. 122, Div. 7).

Zoning, where allowed & definitions

Not listed on our page: Verify with the city/county before renting.

Night limits, minimum stays & occupancy

Not listed on our page: Verify with the city/county before renting.

Fees, penalties & pending changes

Not listed on our page: Verify with the city/county before renting.

Taxes & who collects them

Register / account for FL state sales tax (6%)
Register / account for Monroe County surtax (1.5%)
Register / account for Local tourist/transient taxes (5%)
What Airbnb collects: Airbnb collects state 6% + surtax only. Monroe County's 5% tourist development tax is NOT on Airbnb's list: register and file it yourself with the Monroe County Tax Collector.
Vrbo and direct bookings: check which taxes Vrbo collects in your area; for direct bookings you collect and remit all of them yourself.
Mandatory cleaning fees charged to guests are taxable as part of the rental (state, surtax and tourist tax). Only an optional, separately itemized fee the guest can decline is excluded (FL Admin. Code 12A-1.061).

Total rate: 12.5%. Monroe local option transient rental tax 5% (DOR DR-15TDT), collected by the county. Calculate.

HOA / condo check

Read your declaration, bylaws and rules for rental bans, minimum terms, caps and approval requirements.
Get any association sign-off or approval letter your city or association requires.
See our HOA & condo guide.

Insurance

Confirm your homeowner/condo policy covers short-term rental use, or add a short-term rental policy. Platform host protection is not a substitute for insurance.
Ask your association whether it requires specific liability coverage.

Deadlines

Renew city/county permits or registrations on their schedule (often annually): confirm the date with the office that issued it.
Florida sales and transient rental tax returns: due the 1st, late after the 20th of the month after the reporting period.
Property tax dates: see Florida deadlines.

Official sources

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Is my Key West rental legal? Checklist