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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Homes That Offer Short Stays
85 properties available
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
This charming oceanfront two story townhouse offers uninterrupted water views and the laid-back luxury that Duck Key is known for. Perfect for families seeking a peaceful retreat with easy access to world-class boating, fishing, and waterfront relaxation. Step inside to a bright, coastal-inspired living space with comfortable seating and large wind
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
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.
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
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
Stylish seaside studio situated near the northern end of Marathon, you'll enjoy a convenient location for all your favorite Florida Keys activities - both on and off the water. Additional on-site perks including an oceanfront pool and shady, palapa-style picnic benches let you indulge in waterfront leisure just steps from your front door. Some
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
Located in Marathon, FL, this charming condo is just a stone's throw away from the renowned Sombrero Beach, one of the top-rated beaches in the state. With grocery stores, restaurants, and various retail shops within a two-mile radius, convenience is at your fingertips. Whether you're into fishing, diving, snorkeling, or simply soaking up t
Enjoy a soak in your own private, heated saltwater pool at this lovely duplex! Part of the Tropical Vibes home, this duplex is a charming hideaway with plenty of room to hang out. Open the sizable glass sliding door to create a seamless indoor/outdoor space between the kitchen, living room, and pool deck. Grill up something tasty on the private gas
Treat yourself to a stress-free vacation filled with sun-soaked days when you book your trip to this Key West condo. With room for up to four guests to a shared pool and beach lifestyle, this home will make it easy to slip into vacation mode!Located in the Truman Annex, a quick five minute walk to the beach at Fort Zachery Taylor park, this rental
Breathe the fresh ocean air and gaze upon tropical sunsets on your next trip to Key West with this one-bedroom, one-bathroom condo. You'll enjoy entertainment, private parking, and a great central location that lets you make the most of your vacation. Part of a complex with three other condos in the middle of downtown, you'll be an easy wal
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