Frequently Asked Questions

Understanding rental rules is one of the most important steps when buying a condominium in Key West. The city has some of the most detailed vacation-rental regulations in Florida, and the ability to rent a property can significantly affect its value, lifestyle use, and investment potential.

In Key West, a rental is considered transient if the stay is 28 days or less. Properties rented for less than 28 days must comply with the City of Key West’s transient rental regulations and licensing requirements.

Rentals longer than 28 days are considered non-transient (monthly or long-term rentals) and follow a different set of rules.

Yes. Any property rented for less than 28 days requires a City of Key West transient rental license.

Without this license, owners may only rent the property for 28 days or longer to the same tenant.

Because the city strictly limits new licenses, most properties that legally allow short-term rentals were grandfathered under earlier regulations.

In most cases, new transient licenses are not issued.

The number of licenses is limited and typically tied to specific properties. Buyers interested in weekly or nightly rentals usually must purchase a property that already holds a licensed transient designation.

Because of this restriction, properties with existing transient licenses often command higher market values.

Operating a legal vacation rental in Key West typically requires several registrations and licenses, including:

• City of Key West transient rental license

• Monroe County vacation rental permit

• City and County business tax receipts

• Florida Department of Business and Professional Regulation lodging license

• Tourist tax registration

• Annual fire and life-safety inspections

• A designated responsible rental manager

These requirements help ensure compliance with safety, tax, and zoning regulations.

Properties without a transient license must typically be rented for 28 days or longer to the same tenant.

Advertising or offering rentals shorter than this period without proper licensing is prohibited under city regulations.

These longer-term rentals are commonly referred to as monthly or non-transient rentals.

Yes. Even if the city allows rentals, condominium associations may impose stricter rules.

Associations commonly regulate:

• Minimum rental periods

• Number of rentals allowed per year

• Tenant application and approval requirements

For example, some Key West communities require 30-day minimum rentals, while others require 90-day leases or longer.

Buyers should always review both city regulations and condominium documents before purchasing.

No. Rental eligibility depends on several factors including:

• City zoning regulations

• Whether the property has a transient license

• Condo association rules

• Historic district restrictions

Because of these factors, many condominium communities in Key West are primarily monthly or seasonal vacation rentals or long-term residential homes.

Renting a property without proper licensing or in violation of city regulations can result in:

• Code enforcement fines

• Suspension or revocation of rental permits

• Removal from rental platforms

• Potential eviction of guests

For this reason, buyers considering rental income should confirm licensing status with the City of Key West licensing department before purchasing a property.

Only a limited number of properties in Key West allow true weekly or nightly vacation rentals. These properties must bothhold a valid transient rental license and allow short-term rentals under their condominium association rules.

Many condominium communities require minimum rentals of 30 days or longer, and some require 90-day leases.

Because licensing is limited and association rules vary, buyers interested in vacation-rental income should verify:

• whether the unit has a transient rental license

• the association’s minimum rental period

• any limits on the number of rentals per year

Working with a local real estate professional familiar with condominium regulations can help identify which properties offer the greatest rental flexibility.