Key West Vacation Rental Tips

Choosing a Key West stay mostly comes down to the length of the rental and the license behind it. The City of Key West separates transient rentals (28 days or less) from non-transient rentals (29 days or more). Use Key West and Florida Keys rentals to shortlist, then book on the property site. This page does not replace the first-time checklist, area facts for renters, or the neighborhood guide.

Quick answer

For a stay of 28 days or less in the City of Key West, book only a property licensed for transient rental. City pages (read October 30, 2026) say every residential rental needs a City Business Tax Receipt, and non-transient rentals may not be rented for less than 29 days at a time. The City strongly recommends confirming that a vacation rental is licensed before you send payment, and its Licensing Division answers those questions. We do not rank managers or invent fees.

City of Key West rental rules that affect guests

From the City of Key West Licensing FAQ and Regulatory Licenses page:

Two categories. Transient rentals are 28 days or less. Non-transient rentals may not be rented for less than 29 days at a time. A week-long vacation needs a transient-licensed property.
Every residential rental needs a Business Tax Receipt from the City.
Medallions. The City issues transient rental medallions, a regulatory license that goes with a Business Tax Receipt.
Check before you pay. The City warns that illegal vacation rentals are easy to advertise on social media. It strongly recommends confirming that a rental is licensed before sending payment, and you can ask the Licensing Division by email ([email protected]).

Key Largo, Islamorada, Marathon and Big Pine Key pins are outside the City of Key West and follow other local rules. Read the pin and the booking site.

Open Key West rentals and read the pin’s badge: Key West, Islamorada, Marathon, Key Largo or Big Pine Key.
Narrow with condo, oceanfront, waterfront or pool only if the amenity is a must. Labels are directory filters, not a quality score.
On the booking site, check the minimum stay against your dates. If a City home lists a minimum stay of 29 nights or more, it may be a non-transient rental. Ask before you book a shorter stay.
Book directly on the property or manager site linked from the listing.

What to confirm before you pay

City of Key West vs another Keys town, from the pin address.
For a stay of 28 nights or less in the City, that the property is licensed for transient use. Ask the Licensing Division if you are unsure.
Parking or a parking plan (see Key West beach parking).
Whether the pool is shared, and its rules, if the pool drove the pick.
Airports and drive: Key West airport and getting there.

If one feature decides the trip, start with these Key West and Florida Keys pages; each lists only rentals whose own listing title or website mentions that feature: Key West and Florida Keys rentals with a pool (12), Oceanfront rentals in Key West and Florida Keys (11), Waterfront rentals in Key West and Florida Keys (10), Key West and Florida Keys condo rentals (15). Confirm the feature with the owner or manager in writing before you pay.

FAQ

Can I rent a Key West home for one week?

Only if it is licensed for transient rental. The City says non-transient rentals may not be rented for less than 29 days at a time.

How do I check that a Key West vacation rental is legal?

The City strongly recommends confirming that a vacation rental is licensed before sending payment. Email the Licensing Division ([email protected]) with questions.

Does BnB Search book the stay?

No. Compare on the hub, then finish on the site linked from the listing.

Start browsing stays

Sources

City of Key West — Licensing FAQ (residential rentals) (read October 30, 2026)
City of Key West — Regulatory Licenses (read October 30, 2026)

Key West first-time checklist · Area facts for renters · Neighborhood guide · Vacation rental companies