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,
Homes With Hot Tubs,
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52 properties available
If you're looking for a family vacation in paradise, look no further than this three-bedroom, single-level home in Marathon. The private, outdoor pool is the perfect place to cool off, and the screened patio is ideal for enjoying the great outdoors during the day and retiring to at night for dinner, drinks, and conversation. The central air-con
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
Plan your next getaway to this quaint tropical studio, complete with a well-equipped kitchenette, furnished patio, and access to a swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood, and street parking is available during your stay.Walk two blocks to the southernmost beach fo
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
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
🌴 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
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
This colorful, waterfront home, located right on the canal with a dock, offers easy access to the ocean or the Gulf. This location is the perfect spot for families to build memories while enjoying your favorite watersports. The home has a full kitchen for easy meal preparation and plenty of space for dining both inside or outside on the furnished b
This gorgeous Key Colony Beach home is your passport to the Conch Republic! Boasting canal-front views and direct water access, this five-bedroom home offers a private piece of paradise. Enjoy a sparkling in-ground pool and a furnished patio complete with a gas grill, a dining table, deck chairs, and a palapa hut with an outdoor sofa. The home also
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
A private paradise awaits at this oceanside, canal-front stunner! Along with direct, deep-water canal access and private boat moorage, this custom delight boasts highlights like a waterfall-fed pool, a thatched palm palapa hut furnished for outdoor living, and a deluxe outdoor kitchen outfitted with a grill, a griddle, and a sink. Additional featur
Part of the Papa's Hideaway complex, this charming historic Key West cottage is an ideal home away from home for your next vacation. Thoughtful upgrades include a high-end kitchen, loads of modern amenities, a shared swimming pool, a sundeck, and a tropical courtyard. Street parking is available during your stay.Located two blocks from the southern
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