Florida Keys Condo Rentals

Florida Keys Vacation Condos

Florida Keys condo rentals offer a relaxed, low-maintenance way to enjoy island living, with the comfort of home and the convenience of thoughtful amenities. Whether you are planning a couples trip, family vacation, group getaway, or longer island stay, condos can make it easy to settle in and enjoy the Keys without the upkeep of a larger private home.

Rental Style

Condos & Waterfront Stays

Best For

Couples, Families & Groups

Popular Areas

Key Largo to Key West

Top Features

Pools, Docks & Water Views

Florida Keys condo rentals are not one-size-fits-all. Some offer waterfront or canal-front views, some are located at marina communities, some include boat dock access, and a few may even feature a private pool. Options can range from cozy island condos to larger multi-bedroom layouts, including rentals with up to four bedrooms for families and groups.

  • Great option for couples, families, groups, and extended stays
  • Some condos offer waterfront, canal-front, or marina settings
  • Select rentals may include boat dock access or private pool features
  • Many include kitchens, living areas, balconies, parking, and easy access to local attractions
  • Available across Key Largo, Islamorada, Marathon, the Lower Keys, and Key West

Browse available condo rentals below, or explore nearby options like Florida Keys oceanfront rentals, homes with private pools, and vacation rentals with boat docks.

Florida Keys condo rental with pool, tropical landscaping, and island vacation setting

Rental Highlight

Easy island stays with flexible layouts, water views, pools, docks, and convenient amenities.


Properties Available 78 properties available
Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation.This rental is part of the upscale Sunrise Suites Resort, locat
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Located on the upscale Duck Key in a quiet neighborhood known as the Village in Hawks Cay, this waterfront townhouse offers the ideal restful retreat. Take in breathtaking views of the Duck Key Marina, Toms Harbor, and the Seven Mile Bridge in the distance! Spend leisurely afternoons fishing from the shoreline, right outside your door. You'll a
Oceanfront
- Duck Key
Bedrooms 2 bedrooms
Bathrooms 1 bath
Half Baths 1 half bath
Two floors of wraparound balconies means two floors of stunning views from this peaceful condo. And that's just the beginning - guests can enjoy access to a shared pool (visible from the balconies!) and the use of a shared dock all throughout their stay. Inside the condo, guests will unwind in a stylish space cooled by central air conditioning.
MA130 - Gold Starfish Rating 5 (5)
Condo
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Welcome to your tropical escape in Marathon, FL! This bright and spacious condo combines comfort with adventure, making it the perfect retreat for families, couples, or solo travelers. With a king bed and a double bed, the home easily accommodates your group, while modern amenities—like a fully equipped kitchen (fridge, stove, oven, and dishw
MA226 - Keys Therapy Rating 5 (3)
Dry Lot
- Marathon
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Baths 1 half bath
Whisk your special someone off to this enchanting Key West townhouse. Enjoy the shared pool and courtyard. The family dog is also welcome to join you for an additional nightly fee. Notice: This is in a residential area. Quiet Hours are 10 pm to 8 am. Park your car on the street and walk everywhere! This home is half a mile from the Southernmost Poi
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Escape to the sunshine and soft sands of the Florida Keys with this amazing home in Sunrise Suites Resort in Key West with a shared pool. Sporting updates such as brand-new appliances, new sound-proof flooring, and a stackable washer/dryer, your stay is guaranteed to be a comfortable one.Back at home, you can stroll down a wooden walkway past a pri
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Welcome to your slice of paradise in Key West's coveted Truman Annex. Tucked within the charming Shipyard community, this inviting townhome places you in the heart of it all—just steps from the sugar-white sands of Fort Zachary Taylor Beach and a short stroll to Mallory Square's legendary sunset celebrations. With Duval Street only two blocks away,
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
Ease into the pleasures of a tropical vacation with this one-bedroom, one-bathroom condo in Key West. With a charming atmosphere, entertainment, and two private parking spaces to save you any headaches, you'll speak nothing but praise during your stay in paradise!Located in the downstairs of a historic building just one block from the excitement of
KW31A - Gardenia Getaway Rating 5 (229)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway lived a few houses down, it was home to a popular Cuban bodega. From the 1980s through the turn of this century, potter Charles Pearson
KW353A - The Coral Cove Rating 5 (74)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway!Located right near the water, you'll be in a prime spot to sample all of the island's many charms. Easily walk or bike to popular Smathers Beach, a great place to rent
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Ma
KW80FLR - Paradise Suite Rating 5 (13)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Half Baths 1 half bath
Dog Friendly Dog Friendly
Fisherman's Retreat is the perfect home base for your fishing trip; it's conveniently located in the fishing community of Conch Key, where you can enjoy the use of the deepwater docking out back with easy access to the open water as well as the fish cleaning table and bait freezer. These two half-duplex, studio apartments may be rented indi
Canalfront
- Conch Key
Bedrooms 2 bedrooms
Bathrooms 2 baths

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