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Key West Vacation Rental Condos and Townhomes
In the Keys, there are area specific rental licensing rules and restrictions for single family homes. The City of Key West is regulated differently than the rest of Unincorporated Monroe County. Condos and townhome complexes can also have their own rules and regulations! On this page, we focus on those short term condos and townhomes.
For other types of short-term Key West rentals, click here.
Key West vacation rentals come in three forms, weekly or daily rentals (one day rentals is called transient rentals) and monthly rentals, which have a minimum 28-day rental restriction. These three forms of rentals have different rental income and return on investment.
In order to have a transient or daily short-term rental in Key West, a property owner must have a City of Key West transient license. There is a finite supply of such licenses in Key West and the property itself must qualify for a transient license! Most properties are sold with those licenses, but occasionally a hard to get, and valuable license can come up for sale on the open market.
The occupancy rate for short term rentals in Key West is very high as there is demand for rentals all year in our tropical paradise! That makes Key West, the most vibrant city in the Keys, and an excellent investment opportunity. Rental rates have been steadily increasing over time, which along with property appreciation, makes for an excellent investment!
Each property below must be individually confirmed as to being a legally allowed short term vacation rentals through the City of Key West. Various by-laws may apply that may impact the ability to apply for and receive a vacation rental license. Regulations may change over time.
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Beautifully updated and styled with plush new interior designed furnishings, 401 Emma Street Unit H is a vacation rental townhome that has BOTH Ocean and Harbor views in ...
- 2 Beds
- 2 Baths
- 618955 MLS
Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-b...
- 3 Beds
- 3 Baths
- 616322 MLS
Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment pot...
- 2 Beds
- 3 Baths
- 616792 MLS
Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment pot...
- 2 Beds
- 3 Baths
- 616791 MLS
TRANSIENT investment opportunity awaits. Spacious 2bd/2ba situated in the centrally located waterfront community of 1800 Atlantic. Large covered balcony overlooks a lush ...
- 2 Beds
- 2 Baths
- 620154 MLS
Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one of Key West's sought-after waterfront resorts, 1800 Atlantic Blvd. A completel...
- 2 Beds
- 2 Baths
- 616994 MLS
Discover relaxed coastal living in this three-level townhome located within the gated Seaside Residence community—an incredible opportunity to own in a sought-after resor...
- 2 Beds
- 3 Baths
- 617823 MLS
This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited...
- 2 Beds
- 2 Baths
- 619022 MLS
An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breez...
- 2 Beds
- 2 Baths
- 618827 MLS
HARBOUR PLACE | TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views from the pool and patio areas. Unit 102 has an open floor plan that seamlessly ...
- 2 Beds
- 2 Baths
- 619263 MLS
Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside ...
- 1 Beds
- 1 Baths
- 615746 MLS
Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside ...
- 1 Beds
- 1 Baths
- 615748 MLS
Welcome to 1421 12th St, a stunning oasis nestled in the heart of Key West. This charming property perfectly combines island living with modern convenience, offering an e...
- 3 Beds
- 3 Baths
- 618748 MLS
This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. ...
- 2 Beds
- 2 Baths
- 619778 MLS
Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatil...
- 3 Beds
- 3 Baths
- 612215 MLS
Embrace the laid-back lifestyle of the Florida Keys in this waterfront two-bedroom, two-bathroom condominium with beautiful water views. Soaring vaulted wood-beamed ceili...
- 2 Beds
- 2 Baths
- 620697 MLS
Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers th...
- 2 Beds
- 2 Baths
- 620451 MLS
Located in the desirable Truman Annex Shipyard community, this beautifully updated first-floor condominium offers 2 bedrooms, 1 bath. The newly renovated kitchen feature...
- 2 Beds
- 1 Baths
- 620043 MLS
Discover the ultimate fusion of luxury and part time usage with this transient-licensed, 2-bedroom, 2.5-bath condo in Key West. Perfectly suited for vacation rentals, it ...
- 2 Beds
- 3 Baths
- 612214 MLS
Rare opportunity to own a transiently licensed 2-bedroom, 2-bathroom condo in Key West, offering exceptional flexibility for personal use and short-term vacation rental i...
- 2 Beds
- 2 Baths
- 620198 MLS
Freshly relaunched and ready for its next chapter, this beautifully maintained 2-bedroom, 1-bath condo in Shipyard offers the Key West lifestyle everyone is looking for: ...
- 2 Beds
- 1 Baths
- 620303 MLS
Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of BEACHFRONT living at the Key West Beachside Resort and Residences. This stunning Gulf View, Waterfront corn...
- 1 Beds
- 2 Baths
- 618838 MLS
Substantial price improvement. Motivated seller. This well-maintained 2-bedroom condo has just hit the market and is truly priced to sell. Offered turnkey and newly fur...
- 2 Beds
- 2 Baths
- 619590 MLS
Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includes two luxurious, fully furnished units—a Signature King Room and a Resort View ...
- 2 Beds
- 3 Baths
- 612515 MLS
Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers...
- 2 Beds
- 2 Baths
- 620466 MLS
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