Can I buy a vacation rental property in the Keys?

Vacation Rental Regulations in the Florida Keys

If you are considering buying a vacation rental property in the Florida Keys, the first thing to understand is that short-term rental regulations are not uniform across the islands. Whether you can legally rent your property for less than 28 days depends on the specific land-use district where the property is located and the municipality that governs it.

Monroe County (Unincorporated Areas)

In unincorporated Monroe County, a “special vacation rental” generally means a dwelling rented for less than 28 days. Whether it is permitted depends on the property's specific land-use district and location.

Short-term rentals are prohibited in certain land-use districts, including:

• Improved Subdivision (IS) — Standard residential subdivisions where vacation rentals are not allowed
• Urban Residential Mobile Home (URM) — Mobile home park districts
• Improved Subdivision Masonry (IS-M) — Masonry residential subdivisions

Vacation rentals may be permitted in certain other districts, including:

• SR (Suburban Residential)
• MU (Mixed Use)
• UR (Urban Residential)
• IS-V (Improved Subdivision Vacation Rental) — Specifically designated vacation rental subdivisions
• OS (Offshore Islands)

Where a vacation rental is permitted, a Special Vacation Rental Permit may be required. Compliance with annual vacation-rental permit requirements, fire and life-safety inspections, vacation-rental manager requirements, business tax requirements, advertising restrictions, occupancy requirements, parking requirements, local zoning restrictions, and HOA or condominium restrictions is typically mandatory. Monroe County states that vacation-rental units require a licensed vacation-rental manager in applicable areas, and business tax licensing is also required.

The Biggest Mistake Investors Make

A property being advertised on Airbnb or VRBO does not prove it can legally continue operating as a vacation rental after purchase. The special vacation-rental permit is nontransferable: a change in ownership requires the new owner to obtain a new permit. A buyer should never assume “the seller is already making money on Airbnb, so I will continue.” You must verify that you personally can legally operate the rental after closing.

Key West Has Its Own Rules

Key West operates under its own licensing system and regulations, separate from Monroe County. The city maintains a map and list of licensed transient properties and defines transient accommodations as properties rented for less than 30 days or one calendar month. The City of Key West specifically warns buyers to verify a vacation rental is actually licensed before relying on its rental status. If you are looking at Key West, you need a separate review of the city's regulations.

What to Ask Before You Buy

Before buying an investment property, ask your agent, the title company, or your attorney to verify: “Is this exact parcel legally eligible for the intended rental period, and can the buyer obtain the required permit or license after closing?” Do not rely solely on the MLS description. A call to Monroe County or the city planning department can save you from a costly mistake.