Homes with Private Pools in the Florida Keys
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.
Note: Pool availability and heating options vary by property. Some homes offer heated pools during cooler months—please refer to individual property descriptions for details.
A Pool Just for You
No crowded resort decks, no waiting for a chair—just your own private oasis. Kids can swim and play freely while you relax poolside at your own pace. Whether it's a refreshing dip before heading out on the boat, cooling off after a day in the sun, or enjoying a quiet evening float under the stars, your pool is always ready.
The Best of Both: Water + Private Pool
Spend your morning out on the water—boating, fishing, or exploring the clear blue waters of the Keys—then return home, rinse off, and jump into your private pool for round two of relaxation. With both the ocean and your pool just steps away, you have the flexibility to enjoy the best of island life, no matter the weather or conditions.
Space for the Entire Group
Florida Keys vacation homes with private pools offer plenty of room to spread out. With multiple bedrooms, full kitchens, and open living spaces, these homes are ideal for families and groups. Gather for meals, relax after a day on the water, and enjoy the comfort of having your own space to recharge.
Poolside Dining & Outdoor Living
Many pool areas are designed for easy outdoor living, with grills, dining tables, loungers, and shaded seating. Cook fresh seafood, enjoy a casual lunch by the pool, or unwind with a drink as the sun sets. It’s a simple, relaxed way to enjoy time together without ever leaving your home base.
Fun for Everyone
- For Kids – A safe, easy place to swim and play anytime.
- For Parents – A private, peaceful setting to relax and unwind.
- For Everyone – A central gathering space for conversation, games, and evenings spent together.
Book Your Florida Keys Getaway with a Private Pool
From the Upper Keys to Key West, vacation rentals with private pools offer the perfect blend of relaxation and convenience. With space to spread out and your own pool to enjoy, it’s an easy way to elevate your Florida Keys experience.
Browse our homes with private pools and start planning your next island escape.
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Oceanfront Rentals in the Florida Keys,
Pet Friendly Vacation Rentals,
Homes With Boat Docks,
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52 properties available
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An escape to Marathon never looked so good! Yellowtail House is perched in the heart of all the actions, so you will have no delay in checking out pristine beaches, local attractions, ample shopping options, and an abundance of tasty restaurants within walking distance of home base. And, when you really want to indulge in a bit of coastal adventure
Bask in the tropics of Key West at this inviting cottage with a private heated pool and a lush backyard garden. This lovely cottage is located in Old Town near Duval Street, minutes from restaurants, museums, and the daily sunset celebration at Mallory Square. Stay cool with air conditioning, cook up food on the gas grill, and dine outside on pleas
Your Waterfront Escape in the Heart of Islamorada Awaits! Welcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfec
Dream Vacation Awaits Experience the perfect Florida Keys getaway at this spacious waterfront home in Marathon! Boasting a prime location on the canal, a private heated pool, a relaxing spa, and a 30-foot deep-water dock, this home is a boater’s dream. Enjoy breathtaking canal views from your spacious patio, complete with an outdoor kitchen,
Whether it's the textured shiplap walls, the sparkling private saltwater pool, or the lovingly curated decor, you're sure to find something you love about this wonderful home. In the spirit of Key West, you'll find nods to Ernest Hemingway, the nautical culture, and much more. The stunning full kitchen includes full-size appliances, two
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 oasis in Marathon, FL! This beautiful home is the perfect retreat for families and adventure seekers alike. With multiple bedrooms featuring a luxurious king bed, a cozy queen bed, and fun bunk beds, everyone will have their perfect place to rest after a day of exploration. The home is equipped with modern comforts includin
What's better than a Marathon getaway when it comes to coastal adventures and dreamy days of sweet sunshine? Treat yourself to a perfect getaway and make this stunning retreat your home base today, as it boasts four spacious bedrooms, room for a boat on the private, 25-foot dock, a private pool (heating available), and gorgeous views! The inter
Nestled in the heart of Marathon, FL, this charming house offers a serene retreat with stunning water views and a private dock along the canal. The abundance of natural light throughout the home creates a warm and inviting atmosphere, perfect for unwinding and enjoying the picturesque surroundings. With a double driveway, there's ample parking
Enjoy the unbeatable location of this two-story home only a block away from Duval Street. Take advantage of the large open concept living room, kitchen, and dining spaces while relaxing indoors. You can also beat the Florida heat by cooling off in the pool. This home is ready-made for group getaways with plenty of space to hang out together while s
Spend some time in the Florida Keys at this three-bedroom, canalside rental with a furnished and covered patio, private pool, a 75-foot dock, and plenty of room inside the home for up to seven guests (six comfortably). The family dog is also welcome to join you here for an additional nightly fee. This vacation rental is conveniently located right o
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