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,
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Homes With Boat Docks,
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52 properties available
Please note: This home requires a minimum stay of 28 nights or longer, as enforced by the HOA. No exceptions can be made. Welcome to Conched Out Cottage, your ideal long-term island escape in the heart of Old Town Key West. This charming, dog-friendly monthly rental is perfect for small families, couples, or close friends looking to settle into the
Plan your next Florida escape at this charming, waterfront home in Marathon, where the vibrant nautical decor and bold blue accents create a welcoming coastal retreat. When you want to venture out, discover great local restaurants and attractions, including the Marathon Air Museum and Florida Keys Aquarium Encounters. You can also launch from the p
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
Slip into a modern duplex with distinctly bright Key West vibes! One of the two properties to rent at the Tropical Vibes house, this duplex is full of comfy details and punches of color. Not least of which is the home's star: a brilliant private saltwater pool (yes, it's heated!). You can start your vacation off right kicking back and enjoy
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,
Casual elegance and lush tropical foliage await at this beautiful Key West home only blocks from Higgs Beach! Boasting a private pool completely surrounded by a rustling wall of palm trees, this upscale rental offers a private, tranquil getaway right in the bustling heart of Key West. This home lies just two blocks away from Higgs Beach and the Edw
With beautiful views of the gulf, a brand new pool, and a newly remodeled interior, this open and spacious two-bedroom home is located on a deepwater canal that can accommodate large boats, making it the perfect place to stage a fun-filled vacation with family and friends. Head down to the private dock and untie the boats to take the family out for
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
Experience Key Largo at its finest when you book a stay at Afternoon Delight! Nestled alongside the water and equipped with a spectacular list of private amenities, your vacation will be shrouded in sunshine, lined by palms, and hugged by the sea breeze. Spend your days splashing in the heated pool, throwing cookouts for your family (thanks to the
Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include n
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
This charming Key West style home features a beachy and clean modern interior decor that will let you truly unwind and feel as you're already at the beach! It's fully gated for privacy and boasts two covered porches equipped with comfortable seatings. The property has a large yard with beautiful mature trees and established landscaping. The
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