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Summerland Key, FL
Generally Investor Friendly
Local STR Agent

Yes, short-term rentals are explicitly allowed in Summerland Key, Florida, but only under specific conditions and with proper permits. Summerland Key operates under Monroe County jurisdiction for vacation rental regulations. Short-term rentals are defined as rentals of less than 28 days duration, and Monroe County maintains strict zoning restrictions and permit requirements. Properties must be located in approved zoning districts (SR, MU, UR, IS-V, OS) and obtain a Special Vacation Rental Permit before operation.
First, confirm your property is in an approved zoning district:
Use the Vacation Rental Map Restrictions to verify your property's zoning classification.
Apply for the following in sequence:
Schedule and pass the mandatory Fire and Life Safety Inspection based on your property size.
Set up systems to collect and remit applicable taxes (see tax section below).
All advertisements must include the 28-day minimum stay requirement and the property's vacation rental license number.
Application: Initial Special Vacation Rental Application
Mandatory for both initial permits and renewals
Monroe County Planning & Environmental Resources
Monroe County Fire Marshal's Office
Monroe County Tax Collector
Monroe County Code Compliance
Important Note: This guide is based on Monroe County regulations as they apply to Summerland Key. Property owners should verify current requirements with the Planning & Environmental Resources Department before making any investment decisions, as regulations may change.


Summerland Key, FL, is an inviting destination in the Lower Florida Keys, known for its tranquil atmosphere and beautiful surroundings. It is located approximately 24 miles east of Key West, the closest major city. With a small population, Summerland Key embodies the serene and picturesque charm of the Florida Keys.
The island is well-known for its easygoing lifestyle and vibrant marine life, making it a popular spot for diving, boating, and fishing enthusiasts. It is part of Monroe County and offers visitors a peaceful retreat with quick access to the bustling attractions and cultural landmarks of nearby Key West.
One notable site on the island is the Florida Keys Over-Sea Railroad Bridge, which offers stunning views of the surrounding waters. Nearby attractions include the Bahia Honda State Park, known for its exceptional beaches, snorkeling opportunities, and historic bridge.
Summerland Key's appeal for short-term rentals is reinforced by its proximity to both natural wonders and cultural sites, allowing visitors to experience the best of the Florida Keys while enjoying a quiet and private locale.
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