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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52 properties available
This spacious home offers a great ocean view and is located on a canal with a dock and room for a boat up to 24 feet in length. Spread out over two levels, this spacious getaway features a full kitchen, a lower-level kitchenette, a patio, and a private, outdoor pool. This rental is an easy walk or bike ride to Sombrero Beach as well as the Turtle H
Aglow with natural light, this very inviting, waterfront retreat is ready to host you and your guests here in Marathon! Head out on the canal in the provided kayak, cruise around the neighborhood on one of the bikes, or hop in the car and discover a number of local attractions including the Marathon Community Theatre, Inc., Florida Keys Aquarium En
This home features impressive sunset views over the open Gulf! The whole house is set up for a beach-loving family. Located on a completely fenced 1/4 acre property, this home allows plenty of parking for a boat trailer. The new dock can fit a large boat, and the large swimming pool and tropical hut are perfect for relaxing after boating. Guests ca
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
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
Escape to your own private tropical oasis at this stunning pool home in Big Pine Key, Florida. This spacious house features a large balcony overlooking a plugged canal, perfect for enjoying your morning coffee or evening cocktail while taking in the serene water views. The covered porch with sun shades provides a comfortable spot to relax and unwin
🌴 TROPICAL BLISS ESCAPE – Key Largo Waterfront Getaway Escape to the laid-back charm of Key Largo, Florida, and discover the perfect blend of relaxation and adventure at this 3-bedroom, 2-bath waterfront retreat. With a private pool, guest dockage for boats up to 28 feet, and unbeatable access to both Florida Bay and the Atlantic Ocean, this
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
This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the
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
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
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