Key West is one of the most tightly controlled vacation rental markets in Florida. The island is small, housing is scarce, and the city treats nightly rentals very differently from monthly ones. Before you buy or list, the first question is not price or design but whether the property is legally allowed to rent to guests for short stays at all.
As of 2026, the City of Key West defines a transient rental as a residential unit rented for 28 days or less. Anything shorter than 29 days needs a city transient rental business tax receipt plus an active State of Florida vacation rental license from the Department of Business and Professional Regulation, and the city asks for a copy of that state license at every renewal. Transient rental rights are limited and tied to specific properties, so most homes in residential neighborhoods can only be rented for 29 days or more. Always confirm that a property holds a valid transient license with the city's Licensing Division before you buy or advertise. The city even warns renters that illegal rentals are commonly advertised online.
Taxes come in two layers:
The Tax Collector states plainly that it has no agreement with Airbnb, Vrbo or similar platforms, and that they do not remit the 5% tourist development tax. You or your manager must file it. Verify current rates and rules with the city and county, since rules change.
We did not find a reliable published price survey for Key West turnovers, so compare quotes. Expect island pricing. Labor is tight because many workers commute from the Middle and Lower Keys, parking in Old Town is limited, and supplies cost more to get here. Pools are common in conch houses and compounds, salt air is hard on fixtures, and sand and humidity add time to every clean. Ask whether quotes include pool checks, linens and restocking.
High season runs roughly from mid-December through April, when winter visitors and spring breakers fill the island. Fantasy Fest in late October and holiday weeks are also busy. Late summer and early fall are the slowest months and overlap with hurricane season, which runs June through November. Lock in your cleaning team before winter, and agree in advance on who secures the property and checks for damage when a storm threatens.
Only if the property holds a city transient rental license and a state vacation rental license. Without one, the city requires stays of 29 days or more.
No. The Monroe County Tax Collector says platforms do not remit the 5% tourist development tax, so you must register and file monthly.
Late summer into early fall is usually quietest, and it overlaps with hurricane season. Mid-December through April is the busiest stretch.
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