Florida Keys Condo Rentals
A Florida Keys vacation home with a private pool offers the best of both worlds—days spent on the water and a private, relaxing space to unwind together. Whether you're staying in Key Largo, Islamorada, Marathon, or Key West, having your own pool makes island living even more comfortable and convenient.
Florida Keys condo rentals offer a relaxed, low-maintenance way to experience island living, with the comfort of home and the convenience of resort-style amenities. Whether you're staying in Key Largo, Islamorada, Marathon, or Key West, condos provide an easy, comfortable home base for couples, families, and small groups.
Easy Vacationing
Condos are designed for simplicity. With everything you need in one place—kitchen, living area, and bedrooms—you can settle in quickly and focus on enjoying your time in the Keys. Many communities also offer elevators, on-site parking, and managed grounds, making your stay seamless from arrival to departure.
Resort-Style Amenities
One of the biggest advantages of condo rentals in the Florida Keys is access to shared amenities. Many communities feature pools, hot tubs, fitness centers, tennis or pickleball courts, and marina access. Some even offer private beaches or waterfront lounging areas—perfect for relaxing between outings.
Waterfront Views & Prime Locations
Florida Keys condos are often located right on the water, offering views of the Atlantic Ocean, Florida Bay, or scenic canals. Whether you're enjoying sunrise from your balcony or watching boats come and go from a marina, condo living keeps you connected to the water.
Many properties are also conveniently located near restaurants, shops, and local attractions, making it easy to explore without going far.
Ideal for Couples & Smaller Groups
Condos are a great fit for couples, small families, or travelers looking for a more compact, efficient space. With options ranging from one-bedroom units to larger multi-bedroom layouts, you can find a setup that matches your travel style without sacrificing comfort.
Lock-and-Leave Convenience
Planning a day on the water or heading out to explore? Condo rentals offer peace of mind with secure buildings and easy “lock-and-leave” convenience. Come and go as you please, knowing your home base is simple to manage and ready when you return.
Book Your Florida Keys Condo Getaway
From waterfront views to resort-style amenities, condo rentals in the Florida Keys offer an easy, comfortable way to enjoy island living. Whether you're planning a relaxing escape or an activity-filled getaway, condos provide the perfect balance of convenience and connection to the coast.
Browse our Florida Keys condo rentals and start planning your next island stay.
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Oceanfront Rentals in the Florida Keys,
Homes With Private Pools,
Pet Friendly Vacation Rentals,
Homes With Boat Docks,
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Homes That Offer Short Stays
78 properties available
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
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
Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00amRight in the heart of the action,
Welcome to Sunset Suite -- Catalina Suite 311, your slice of paradise in vibrant Key West! This inviting two-bedroom condo is part of the upscale Sunrise Suites Resort, where tropical comfort meets resort-style amenities.Step onto your private deck to soak in the island breeze, then spend your day swimming in the heated pool, unwinding in the hot t
Part of the Papa's Hideaway complex, this charming historic Key West cottage is an ideal home away from home for your next vacation. Thoughtful upgrades include a high-end kitchen, loads of modern amenities, a shared swimming pool, a sundeck, and a tropical courtyard. Street parking is available during your stay.Located two blocks from the southern
Plan your next getaway to this quaint tropical studio, complete with a well-equipped kitchenette, furnished patio, and access to a swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood, and street parking is available during your stay.Walk two blocks to the southernmost beach fo
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
Tropical comfort abounds when you stay at this wonderful condo on the shores of Key West. Complete with a shared pool & hot tub, tennis courts, and a private, covered parking space, you'll have everything you need for an unforgettable Florida Keys escape. One dog is allowed.Located on the eastern side of the island, this condo is part of the luxuri
Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island! Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any number of delicious restaurants, not to mention famous historical a
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, boasting serene oceanfront views from two private balconies. The top-floor location immerses you in beautiful water views and gentle breezes on your private Tavernier Escape. Enjoy on-site amenities like the community pool and gazebo, a waterfront caf&eac
Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more!Perfectly located between Truman Annex and Bahama Village, this comfortable condo sits only two blocks from the fantas
Live that Florida Keys lifestyle at this bright and beachy waterfront condo built in 2022 and boasting a sparkling community pool and shared dock. Lounge by the pool, or wander over to one of the many restaurants or shops within walking distance on Overseas Highway. Florida Keys Aquarium Encounters, Key Colony Beach Golf Course, Curry Hammock State
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