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,
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Pet Friendly Vacation Rentals,
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Homes That Offer Short Stays
85 properties available
An escape to the Keys is never a bad idea, so treat yourself to a stylish getaway and kick back in bliss here at Coral Delight! Sitting right on the coast, you will have no delay in getting your fill of sweet sunshine, sandy toes, and sun-kissed skin. As soon as you step inside, you will be greeted by the tropical decor, plush furnishings, and plen
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
This second-floor tropical studio has a private outdoor seating area and plenty of space for your vacation crew. Spend time splashing in the shared pool or catch some rays on the sundeck.Located in a residential neighborhood two blocks from the southernmost beach and just one block from Duval Street for the area's best restaurants, shops, terrific
Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home!When you're done swimming in the shared pool or soaking in the shared hot tub, you can towel off and head in
Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large b
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
Step back in time—while enjoying every modern comfort—in this beautifully appointed three-story condo nestled within the legendary grounds of the historic Long Key Fishing Club in Layton, Florida. Once the prized fishing destination of icons like Theodore Roosevelt and Zane Grey, this area was famously known as Henry Flagler’s Lon
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
Sun-soaked days and cool ocean breezes await you when you book your next retreat to this oceanfront Key Largo getaway. Featuring sweeping ocean views and shared amenities like a pool, on-site tennis, and beach access, fun will always be easy to find! Steps from the gently rolling waves, and just over seven miles from the heart of the island, you
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of three condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical vacation!Sitting only one block from the central a
Book this wonderful, ground-level, Old Town getaway with all the comforts of home including central air conditioning and complimentary internet access! This vacation rental features a spacious floor plan with doors that open out to the back patio to create an indoor/outdoor living space. Kick back in the living area and watch your favorite TV show
Set up on the fourth floor with a front-facing view of the adjacent waterway, this comfortable condo is an excellent option for that next romantic escape to the Keys! This property is less than a mile from groceries, shops, and restaurants. Inside this condo, you'll find a well-equipped, full kitchen, a four-seater dining table for mealtimes or
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