Vacation Rental Management
Vacation Rental Management in Key West, FL
At the end of the Overseas Highway, Key West runs on a calendar of its own, and Fairly manages homes here to match it — turnovers, guest care, and the state and county lodging taxes handled on every booking, with listings on Airbnb, Vrbo and Fairly.com.
4.8
Average review in Key West, FL
Fairly is an Airbnb Superhost, and our homes average 4.84 stars across 19,000+ guest reviews. 87% of those reviews are five stars. Better reviews attract better guests, at higher prices, maximizing your revenue.
Key West market overview
Key West sits at the end of the Overseas Highway, closer to Havana than to Miami, and its visitor season runs against the rest of Florida's coast. Travellers come for Old Town's conch houses and the sunset crowd at Mallory Square, for the Ernest Hemingway Home, and for the reef and flats fishing that start a few minutes offshore. Dry Tortugas National Park is reached only by ferry or seaplane from the island.
Demand peaks January through March, when occupancy and nightly rates are both at their highest and a well-run house books out weeks ahead. April tapers, and the market thins through a hot, wet summer to a September floor — the deepest weeks of hurricane season. October turns it back around, Fantasy Fest fills the island, and rates climb through November and December toward the winter peak. The county tourism council publishes the event calendar.
What homes earn in Key West, FL
The chart tracks top-performing Key West rentals on Airbnb and Vrbo — homes carrying a guest review score of 4.8 or better and available or rented at least 300 days a year. Key West is one of the strongest earning markets Fairly follows, and its shape matters as much as its level: winter carries the year here, so a home that is listed, priced and fully staffed from January through March captures most of what it will earn. You can customize a projection for a specific home.
| Month | Total rent | Occupancy | Avg. daily rate |
|---|---|---|---|
| Jan | $11,967 | 76% | $781 |
| Feb | $12,111 | 84% | $812 |
| Mar | $14,188 | 78% | $825 |
| Apr | $10,573 | 68% | $758 |
| May | $8,532 | 58% | $692 |
| Jun | $6,789 | 53% | $639 |
| Jul | $6,595 | 55% | $615 |
| Aug | $5,203 | 45% | $543 |
| Sep | $3,432 | 39% | $473 |
| Oct | $6,141 | 48% | $600 |
| Nov | $8,439 | 57% | $717 |
| Dec | $10,839 | 66% | $745 |
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This is based on properties listed on Airbnb, Vrbo, and Booking.com with an average review score of 4.8 out of 5 or higher, limited to homes available or rented at least 300 days a year. Earnings vary based on the unique amenities and qualities of each home.
Vacation Rental Taxes and Regulations in Key West, FL
Whether your home can be rented short-term
Key West is one of the most restricted rental markets in the country, and eligibility turns on the property, not the owner. A residential dwelling rented for less than 30 days, or advertised to transients, is a transient living accommodation, and unlicensed transient use is prohibited. The licence attaches to the property and passes to a buyer on sale, and the city publishes the address list of every licensed transient property. Most Key West houses are not on it: the city's rate of growth ordinance caps transient units, and the code governing them exists to move existing licences between properties, not to create new ones. Florida law bars local governments from prohibiting vacation rentals, but exempts ordinances that predate the statute — and Key West's do.
A home without a transient licence is not idle: it can be rented by the month or longer, which is how much of the island's rental stock operates.
Lodging and sales taxes
Bookings carry 12.5%. Monroe County levies a 5% tourist development tax on rentals of six months or less, remitted to the County Tax Collector and delinquent after the 20th. Florida adds 7.5% — the 6% state sales tax plus Monroe's 1.5% discretionary surtax — on a single Department of Revenue return. Both reach the whole guest charge, cleaning and pet fees included.
Registering your rental
Start with the state: a DBPR vacation rental licence from the Division of Hotels and Restaurants, dwelling or condominium class, renewed each October 1 in the district covering Monroe. Open the tax accounts next — sales tax with the Department of Revenue, tourist development tax with the County Tax Collector. Every rental property, short or long-term, needs a Monroe County business tax receipt, and one inside the city limits a City of Key West receipt too. The transient licence sits on top, renews by September 30, and carries a fire marshal inspection.
Outside the city limits
City limits cover the island of Key West and Stock Island north of U.S. 1. South of that line unincorporated Monroe County governs: rentals under 28 days are unlawful in several residential land use districts, and elsewhere need an annual special vacation rental permit and a licensed local vacation rental manager.
How Fairly handles it
Fairly registers your home for the Monroe County tourist development tax and the Florida sales tax, then collects and remits on every booking and files each return on schedule. We assist with the DBPR licence, the business tax receipts, and each annual renewal.
Operating a vacation rental in Key West, FL
Salt air and year-round humidity are the standing load here: outdoor hardware corrodes, air conditioning runs twelve months, and hurricane season means shutters, an evacuation plan mid-booking, and a house that closes up fast. Winter is a turnover business — three- and four-night stays back to back from January through March, on Old Town streets where a truck often cannot park at the door.
A licensed transient property also has conditions to keep meeting: the medallion displayed outside, a contact person available 24 hours a day whose name and number are posted on the exterior, a current tenant and vehicle register, and the fire marshal's inspection. Your caretaker is that point of contact — on the island, handling each turnover and walkthrough personally, and close enough to answer a complaint the same hour. You keep final say, and you can change caretakers whenever you want.
Frequently asked questions
Can my Key West home be rented short-term?
Only if the property itself holds a City of Key West transient licence. The licence runs with the property and transfers on sale, and new ones are not issued — the city's rate of growth ordinance caps transient units, so a licence has to come from another property. Check the city's published address list before you buy. Without one, a home can still be rented by the month.
What taxes does a Key West vacation rental pay?
12.5% on stays of six months or less. Monroe County's 5% tourist development tax goes to the County Tax Collector on a monthly return, delinquent after the 20th. Florida's 6% sales tax and Monroe's 1.5% discretionary surtax go to the Department of Revenue on one return. Fairly registers your home for both accounts and collects, remits and files on every booking.
What is Fairly's management fee in Key West?
A flat 20% of rental revenue — one rate, no tiers, no setup charge, no long-term contract. That figure also covers your caretaker, who receives the entire cleaning fee the guest pays plus a share of Fairly's management commission. Paying them that way is why the same caretaker stays with your home through a full Key West winter instead of a rotating crew.
A guaranteed $5,000 increase in earnings
We guarantee that homeowners coming from self management or other managers will make an extra $5,000 in their first year with Fairly.
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or email us at key-west@fairly.com