What Are the Vacation-Rental Rules in the Florida Keys?

If you're thinking about buying a Florida Keys property and using it as a vacation rental, don't assume that owning a home in the Keys automatically gives you the right to rent it by the night or week. Vacation-rental rules are highly location-specific, and the rules can differ between unincorporated Monroe County, Marathon, Islamorada, and Key West.

The first question should always be:

"Is this specific property legally eligible for vacation-rental use?"

That should be verified before purchasing, because a property's current or potential rental income can have a significant effect on its value.

What Counts as a Vacation Rental?

In unincorporated Monroe County, a vacation rental generally means a dwelling rented for less than 28 days. Monroe County

However, the rules are not uniform throughout the Keys because some municipalities have their own regulations.

That's why a buyer shouldn't simply see:

"Vacation rental permitted"

in a listing and assume the property can be operated like an unrestricted Airbnb.

Unincorporated Monroe County

This covers many areas of the Keys outside incorporated municipalities.

The biggest issue is zoning.

Not every residential property can legally be used as a short-term vacation rental.

Monroe County specifically states that vacation rentals are prohibited in certain land-use districts. For example, homes in Improved Subdivision (IS), Urban Residential Mobile Home (URM), and IS-M districts generally cannot be rented for stays of less than 28 days, subject to specific exceptions such as certain gated communities. Monroe County

Other zoning districts may allow vacation rentals, but additional requirements apply.

If the property qualifies:

The owner generally needs an annual Special Vacation Rental Permit before operating the property as a vacation rental. Monroe County

The county also requires a Fire and Life Safety inspection.

Current county-published inspection fees are:

• 1 bedroom — $125
• 2–3 bedrooms — $250
• 4+ bedrooms — $400 Monroe County

The county also requires a vacation-rental manager license, and the manager must meet local requirements, including being available to respond to complaints. Monroe County

Important for buyers

A Monroe County vacation-rental permit is not transferable when the property changes ownership. A new owner must obtain a new permit. Monroe County

So if you're buying a property that is currently operating as a vacation rental, verify that you can obtain the required permit yourself.

Marathon

Marathon has its own vacation-rental licensing system.

The City of Marathon defines vacation rentals as residential units rented for 7 to 28 nights. Rentals of less than seven nights are prohibited. Monroe County

A vacation-rental license is required.

Marathon also requires several other registrations/licenses, including:

• Monroe County Business Tax Receipt
• Monroe County Tourist Tax account
• Florida DBPR lodging license
• Florida Department of Revenue sales-tax identification
• City fire inspection City of Marathon

Occupancy

Marathon limits occupancy to:

Two people per bedroom plus two additional people.

For example, a three-bedroom vacation rental would generally have a maximum occupancy of 8 people, subject to the applicable regulations and property requirements. City of Marathon

Other Marathon rules include:

• Noise restrictions
• Parking requirements
• Trash requirements
• Rules concerning boats and docks
• Hurricane evacuation requirements
• Required rental information
• Vacation-rental permit number in advertising City of Marathon

This is important for anyone considering buying a Marathon property specifically for short-term rental income.

Islamorada

Islamorada has its own vacation-rental licensing and registration requirements.

For 2026/2027, the Village's published vacation-rental application fee is $1,325. Islamorada

The application requires documentation including:

• Monroe County Property Appraiser record card
• Active Monroe County Tourist Development Tax account
• Monroe County Local Business Tax receipt
• Applicable Florida DBPR lodging license
• Property-owner affidavit
• Deed/subdivision/condominium restrictions
• Parking information
• Property manager and secondary contact information Islamorada

A life-safety inspection must be completed and passed before the vacation-rental license is issued. Islamorada

Islamorada also has property-value eligibility criteria.

For 2026 applications, the Village lists assessed-value thresholds of:

• $708,000 for properties in certain Residential High/Mixed Use areas
• $1,062,000 for properties in certain Residential Conservation/Residential Low/Airport areas Islamorada

The thresholds are based on the property's assessed value and applicable Future Land Use Map category.

This is one reason you should never assume that a home can be converted into a vacation rental simply because it is located in a desirable Keys neighborhood.

What About Key West?

Key West is particularly important because the City of Key West has its own vacation-rental regulations and licensing system, separate from the unincorporated Monroe County rules.

For a Key West property, the buyer should verify the property's specific Transient License / vacation-rental eligibility with the City before relying on rental income.

This is especially important because Key West has historically had strict limitations on transient residential rentals and different licensing categories.

So if you're writing this for an Ask Steve page, I would avoid saying:

"You can rent your Key West home for up to 28 days."

That would be too broad.

Instead:

"Key West has its own transient-rental licensing rules, and eligibility depends on the property's specific license, zoning and regulatory status."

Don't Forget the State of Florida

Local approval isn't the only requirement.

Florida treats rentals of six months or less as transient accommodations for sales-tax purposes. The Florida Department of Revenue states that the 6% state sales tax, plus applicable discretionary sales surtax, applies to these rentals. Florida Department of Revenue

Florida counties can also impose local transient-rental taxes, commonly called tourist development taxes. Florida Department of Revenue

So a vacation-rental owner needs to consider both:

State taxes and Local tourist/transient rental taxes.

HOA and Condo Restrictions Matter Too

Even if Monroe County or a municipality allows vacation rentals, the property's:

• HOA
• Condo association
• Deed restrictions
• Subdivision restrictions

may impose additional restrictions.

Islamorada's application specifically requires applicants to provide copies of applicable deed, subdivision or condominium restrictions. Islamorada

So there are really three levels to check:

1. Government rules
   Can this property legally be used as a vacation rental?
2. License/permit
   Does the property qualify for the necessary local license or permit?
3. Private restrictions
   Does the HOA, condo association or deed allow short-term rentals?

All three need to line up.

Can I Buy a Property That Already Has a Vacation-Rental License?

Be careful here.

A property having an existing vacation-rental operation does not necessarily mean the license simply transfers to the buyer.

For unincorporated Monroe County, the county explicitly states that a Special Vacation Rental Permit is nontransferable and a change of ownership requires the new owner to obtain a new permit. Monroe County

That means a buyer should make the purchase contingent on verifying that the property is eligible for the required permit/license.

What Should Buyers Check Before Buying?

If vacation-rental income is part of your purchase decision, I would recommend checking these items before making the property a firm investment decision:

Zoning
Is short-term rental use permitted at this exact address?

Current license
Does the property currently have a valid vacation-rental license or permit?

Transferability
Will the license survive the sale, or does the new owner have to reapply?

Minimum stay
Is the property permitted to rent nightly, weekly, or only for longer stays?

Occupancy
How many guests can legally stay there?

HOA/condo restrictions
Does the association allow short-term rentals?

Taxes
What state and local rental taxes apply?

Insurance
Does the insurance policy permit vacation-rental use?

Flood and hurricane requirements
Does the property have additional requirements because of its location?

Property manager
Is a local manager required?

Fire/life-safety inspection
Does the property meet the applicable requirements?

Why This Matters When Buying a Florida Keys Home

This is particularly important from a real-estate valuation perspective.

Two homes could be nearly identical physically:

Home A

• $900,000
• Vacation rentals prohibited

Home B

• $950,000
• Legally permitted vacation rental
• Strong rental history
• Appropriate license eligibility

The second property may attract a completely different buyer pool because it has potential income-producing use.

On the other hand, a buyer shouldn't simply assume:

"This house earns $100,000 a year on Airbnb, so I'm buying a $100,000-a-year investment."

The income may depend on:

• Existing licensing
• Occupancy limits
• Seasonal demand
• Management costs
• Cleaning
• Insurance
• Taxes
• Repairs
• HOA fees
• Advertising
• Regulatory changes

The most important advice for a buyer:

Never buy a Florida Keys property based on projected vacation-rental income until you have verified that the specific address is legally eligible for the rental use you intend.

A property being advertised on Airbnb or VRBO doesn't by itself prove that the rental is legal or that the required license can be obtained by a new owner.