Running vacation rentals in Key West, where a nightly rental needs a license someone else already owns
If you manage or clean vacation rentals in Key West, the city splits residential rentals at 28 days. A stay of 28 days or less is a transient rental, and the city capped transient licenses long ago, so new nightly or weekly rentals run on a license bought from someone who already holds one. A stay of 29 days or more is a non-transient rental and needs only a business tax receipt, anywhere in the city. Upbridge's AI operations assistant, Cleo, works over WhatsApp with vacation rental operators and cleaning companies and organizes the cleanings and the inventory for each place.
The rules here
Key West's transient limits predate Florida's 2011 limit on local rental rules, which is why they still stand. We read the city, state and county material on October 24, 2026.
| Topic | What it says | Status | Since | Source |
|---|---|---|---|---|
| Two kinds of rental | Every residential rental needs a City of Key West business tax receipt. Rentals are non-transient, which may not be rented for less than 29 days at a time, or transient, for 28 days or less. Transient rentals renew with a copy of an active state license. | In force | FAQ not dated | City of Key West |
| Transient license cap | The Blue Paper reported in 2019 that new transient licenses had been capped since 2002. Keys Weekly reported in May 2022 that the city does not issue new ones, so owners buy an existing license from a private holder, usually for at least $500,000. | In force | Reported 2019 and 2022 | The Blue Paper, Keys Weekly |
| Florida law | Section 509.032(7)(b) bars local rules that prohibit vacation rentals or regulate how long or how often they are rented, but it does not apply to local rules adopted on or before June 1, 2011. The city attorney told commissioners in 2022 that Key West's transient limits are grandfathered and would be lost if changed significantly. | In force | 2026 Florida Statutes | Florida Senate, Keys Weekly |
| Monthly rentals | Keys Weekly reported that a monthly rental is legal in any neighborhood and needs only a $21 annual business license. | In force | Reported May 5, 2022 | Keys Weekly |
| Tourist tax | Monroe County's current tourist development tax rate is 5%, according to the state's 2026 table of local option tourist taxes. | In force | Table of September 4, 2026 | Florida EDR |
The city's FAQ sends readers to its code for the business tax amounts, and we did not find a current count of transient licenses. This is not legal or tax advice, and Upbridge does not file anything for you: no registrations and no tax returns.
How it works on the ground
If you manage both kinds, you run two businesses. Transient units can turn over every few nights, and a monthly unit turns over twelve times a year at most. The cleaning is different too: a monthly guest leaves a lived-in house, with a full fridge and a month of laundry.
Because a transient license is worth so much, it is the most valuable paper in the file. If a unit's license lapses, the owner loses the right to rent nightly, and the city's FAQ says caps mean nothing new is issued unless an existing holder does not renew.
Key West Island News wrote in 2021 that transient and monthly rentals had turned much of Old Town into a visitors' district over two decades. The column lists parking and late-night noise among the neighbors' complaints, which is what the house rules a manager sends guests should cover.
Where Upbridge fits
Upbridge creates the cleaning task when a checkout arrives from Guesty, Hostaway, Lodgify, Uplisting or an iCal link, with a room-by-room photo checklist. You can keep one list for the transient units and a longer one for the monthly turnovers, with the fridge, the laundry and the outdoor shower on it.
Inventory per property deducts what each stay used, so a unit that had three short stays in a week shows its low stock before the fourth. Guests get the guest guide on their phone with parking, the door code and the quiet hours.
If you run a cleaning company in Key West
A day here can hold a quick guesthouse turnover and a half-day monthly reset. The cleaning company account shows every client's checkouts by date on one calendar, so you can give the long jobs the morning, and each client is still yours.
Questions about vacation rentals in Key West
Can I get a new transient rental license in Key West?
Local reporting says no: transient licenses have been capped since 2002, and Keys Weekly reported in 2022 that owners buy an existing one from a private holder. The city's FAQ says capped licenses are only reissued when an existing holder does not renew.
What counts as a transient rental in Key West?
A residential rental of 28 days or less. A non-transient rental may not be rented for less than 29 days at a time.
Can Florida stop Key West from limiting vacation rentals?
Florida law bars local rules that regulate how long or how often vacation rentals are rented, except rules adopted on or before June 1, 2011. Key West's transient limits are older than that.
Sources
Checked on October 24, 2026
- City of Key West, “Licensing Division FAQs”, undated, read October 24, 2026.
- The Florida Senate, 2026 Florida Statutes, section 509.032, read October 24, 2026.
- Florida Office of Economic and Demographic Research, “2026 Local Option Tourist / Food and Beverage / Tax Rates in Florida's Counties”, September 4, 2026.
- Keys Weekly, “Vacation rentals in Key West prey on working residents”, May 5, 2022.
- Arnaud and Naja Girard, The Blue Paper, “What is eating up Key West’s residential housing stock?”, November 4, 2019.
- Key West Island News, “How long before vacation rentals take over my Key West neighborhood?”, April 15, 2021.