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 75 properties available
You’ll feel like the Atlantic Ocean is right outside your door at this stunning oceanfront Casa Clara Oceanfront Getaway in Key Colony Beach. Wake up to spectacular sunrises, spend your days between two private sandy beaches, and take advantage of resort-style amenities—all just steps from your first-floor retreat. 🏝 Location & Sur
14-night minimum 14-night minimum
KC93 - Casa Clara #105 Rating 5 (4)
Oceanfront
- Key Colony Beach
Bedrooms 1 bedroom
Bathrooms 1 bath
Experience the very best of Key West living at this unique Old Town Truman Avenue Eyebrow home. Tucked away in a small, gated community, this luxury two-bedroom retreat showcases tranquil tropical decor and comes well-appointed with all the modern essentials of home. Whether you're visiting with the kids or sneaking away for a romantic couple&#
7-night minimum 7-night minimum
KW335WK - Dancing Palms Rating 5 (29)
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Escape to your new getaway of choice on the Florida Keys! This two-bedroom and two-bathroom condo by Key West has it all, from a fantastic location and dog-friendly accommodations to lovely resort amenities. Back at home, you can soak in the shared swimming pool and hot tub, before drying off and heading inside. Your balcony offers a stunning view
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. Sitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and within easy walking or biking distance from all the main att
KW31C - Jasmine Suite Rating 5 (309)
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
Welcome to Ohana Keys, your island getaway where stress drifts away on the breeze and paradise greets you at every turn. Nestled in the sought-after Kawama Yacht Club, this vibrant townhome offers not only comfort and style but also access to world-class amenities: a private beach with firepits and tiki bars, sparkling pools, a swimmable lagoon, gr
KL201 - Ohana Keys Rating 5 (10)
Condo
- Key Largo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, where serene oceanfront views greet you from two private balconies. Perched on the top floor, your Tavernier Escape offers sweeping water views and gentle breezes that set the tone for a peaceful getaway.Enjoy on‑site amenities including the community poo
Oceanfront
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Welcome to your Keys escape in Tavernier, Florida! This oceanfront condo puts you right at the water’s edge, where endless blue horizons and island breezes set the tone for your stay. Blending comfort with the laid-back charm of the Keys, it’s the perfect retreat for couples, families, or friends ready to soak up paradise. Start your mo
Marina
- Tavernier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Welcome to Periwinkle Place—a bright, dog-friendly escape in the vibrant heart of Old Town Key West! Just one block from famous Duval Street, this charming two-level home offers the perfect blend of island relaxation and city excitement. From your front door, walk to top attractions like the Ernest Hemingway Home & Museum, Key West Lighth
28-night minimum 28-night minimum
Condo
- Key West
Bedrooms 1 bedroom
Bathrooms 1 bath
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 onl
28-night minimum 28-night minimum
Condo
- Key West
Bedrooms 2 bedrooms
Bathrooms 1 bath
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
All the best of Key West is right at your doorstep at this colorful, second-floor condo just across the street from the gorgeous aquamarine water the Keys are known for. Smathers Beach is just down the road, and all the restaurants, bars, and cafés of Duval St. and the historic district are an easy two-mile drive or bike ride away. Onsite am
28-night minimum 28-night minimum
Oceanfront
- Key West
Bedrooms 2 bedrooms
Bathrooms 2 baths
Dog Friendly Dog Friendly
Experience the laid-back charm of the Florida Keys from this beautiful waterfront condo, built in 2022 and designed for the perfect island getaway.Whether you're seeking adventure on the water or a relaxing escape in the sunshine, this bright and beautifully appointed coastal retreat offers everything you need to make unforgettable memories.Sta
7-night minimum 7-night minimum
Condo
- Marathon
Bedrooms 1 bedroom
Bathrooms 2 baths

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