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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
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
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
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
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
Elegant, peaceful and turn-key, this light-filled, Old Town condo is just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its ...
- 2 Beds
- 2 Baths
- 618827 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
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
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
- 621056 MLS
Exquisite, turnkey resort living awaits in this fully furnished 2-bedroom, 2-bathroom oceanfront condominium, offering an effortless transition into Key West luxury just ...
- 2 Beds
- 2 Baths
- 621152 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
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
Positioned in the coveted X flood zone, this 2-bedroom, 2-bathroom townhome perfectly blends Old Town charm with modern convenience. As one of only two units in an exclus...
- 2 Beds
- 2 Baths
- 621130 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
2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATR...
- 2 Beds
- 2 Baths
- 620647 MLS
Enjoy the largest floor plan in the Santa Clara building with this spacious 2-bedroom, 2-bath condo in the heart of New Town Key West! Welcome to easy island living in...
- 2 Beds
- 2 Baths
- 619027 MLS
Experience Key West sunsets and ocean breezes from this TOP-FLOOR unit! This one-bedroom, one-bathroom residence boasts a spacious and practical floor plan with private b...
- 1 Beds
- 1 Baths
- 619359 MLS
IMPORTANT UPDATE TO NOTE: SELLER WILL PROVIDE A $5,000 CREDIT THAT CAN BE USED FOR CLOSING COSTS OR CONDO FEES!! Excellent as an investment, primary residence, seco...
- 1 Beds
- 1 Baths
- 616493 MLS
Charming second-floor 1 bedroom, 1 bath condominium featuring a functional layout with a kitchen that offers modern appeal and a comfortable living space enhanced by tile...
- 1 Beds
- 1 Baths
- 619131 MLS
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