Compare Vacation Rentals with Pools in Florida Keys, FL

Directly across from the Olympic-size swimming pool and tennis/pickleball courts, this apartment in Tavernier, the southernmost point of Key Largo, is 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.
This apartment offers a fully equipped kitchen with multiple coffee brewing options, a dedicated workspace with secure Wi-Fi, and resort amenities including a sandy beach with a pier, marina, and boat ramp, perfect for a getaway with a pool.

This Marathon apartment offers a private, heated swimming pool and is located just 300 feet from the beach entrance, providing convenient off-water proximity to the Gulf of Mexico.
With 4 bedrooms, this turn-key accommodation comfortably accommodates 10+ guests and features a BBQ patio, a private guest beach with kayaks and paddleboards, and a powered boat dock on the Gulf of Mexico.

Located in Marathon's Coral Lagoon neighborhood, this resort offers direct waterfront access with an on-site marina and private boat ramp, just a short drive to Sombrero Beach, the Turtle Hospital, and watersports operators.
This 1430 sq ft resort villa comfortably sleeps 8 guests and features a heated saltwater swimming pool, a balcony with marina views, a gourmet kitchen, and a nautical-themed interior, perfect for a memorable getaway with a pool.

Located in Tavernier, this holiday home is a 13-minute walk from Harry Harris Park Beach and 3 miles from Pigeon Key.
This 850 square foot house offers 2 bedrooms, 2 bathrooms, and accommodates up to 11 guests with a private hot tub and free WiFi, perfect for a relaxing getaway.

Ocean Shores Villa 3 in Key Largo offers a prime location, situated just 4.1 miles from John Pennekamp State Park and 4.2 miles from Dolphin Cove, perfect for aquatic adventures.
This family-friendly house features 2 bedrooms, 2 bathrooms, and a fully equipped kitchen, plus a private balcony and an outdoor swimming pool for a complete getaway.

Enjoy prime ocean and marina views from this recently renovated 1350 sq. ft. apartment in Key Largo, located within the gated Kawama Yacht Club directly on the Atlantic Ocean coast and adjacent to John Pennekamp Coral Reef State Park.
This family-friendly apartment offers direct Atlantic Ocean access, three heated saltwater swimming pools, a saltwater lagoon, and complimentary marina amenities, making it an ideal getaway with a pool.

Experience unique waterfront living at Aqua Lodge Houseboat "Calypso," a resort located at Mangrove Marina in Tavernier, offering direct access to the bay waters.
This houseboat resort features 3 bedrooms and 2 bathrooms, providing an immersive Keys life experience with a swimming pool and opportunities for fishing, skiing, and diving.

Discover a unique tranquil oasis cove location within Community Harbor, offering a peaceful retreat at Mile Marker 91.7 Bayside in Tavernier, between Key Largo and Islamorada, close to prime fishing and diving destinations.
This houseboat accommodation features a swimming pool and offers resort-style amenities within Aqua Villas at Mangrove Marina Resorts, perfect for a getaway with a pool.

Offering exclusive quarter-mile private beach access on Long Key, this resort is situated between Islamorada and Marathon.
Enjoy a relaxing stay at this resort with a pool, featuring complimentary boat docking, sea kayaks, paddleboards, and on-site dining at the Florida Boy Bar and Grill.

Experience a prime oceanfront resort location in Tavernier, Florida Keys, offering direct access to a private beach and an on-site marina, just moments from local dining and aquatic adventures.
This one-bedroom, one-bathroom apartment is perfect for up to 4 guests and comes with a swimming pool, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher for a comfortable stay with a pool.

Located in Marathon, this house is less than 0.6 miles from Florida Keys Aquarium Encounters and 1.1 miles from Captain Hook S Marina Dove Center.
Enjoy a relaxing stay with a swimming pool with a view, an on-site restaurant, and a children's playground, perfect for families seeking a getaway with a pool.

Enjoy a prime location in the exclusive Venture Out gated community on Cudjoe Key, just 23 miles from Key West.
This apartment offers direct access to a private ramp for kayaks and paddleboards, only 85 yards away, and features a swimming pool for your enjoyment.

Enjoy an upscale oceanfront resort experience in Key Largo, conveniently located 3.3 miles from Pigeon Key and 5.6 miles from John Pennekamp State Park.
This spacious 3-bedroom, 4-bathroom villa offers a private balcony with garden and ocean views, outdoor swimming pool, hot tub, and free WiFi, perfect for a getaway with a pool.

Located in Key Largo, this apartment is near the Caribbean Club Bar and Christ of the Abyss, offering convenient access to local attractions.
Enjoy a comfortable stay with family and friends in this spacious apartment featuring 3 bedrooms, 3 bathrooms, and a swimming pool, perfect for a memorable getaway.

Direct ocean access awaits at this waterfront apartment in Marathon, just 500 feet from Sombrero Beach and 1 minute from grocery stores.
This fully furnished 2-bedroom apartment accommodates up to 6 guests and features a private heated swimming pool, a private dock, and a balcony with stunning ocean views, perfect for boaters and watercraft enthusiasts.

Enjoy a peaceful retreat in this spacious South Miami apartment, conveniently located in a quiet residential neighborhood just 2 miles from Zoo Miami.
This family-friendly apartment accommodates up to 12 guests and features a private swimming pool, an outdoor patio, and a fully equipped kitchen, perfect for your next getaway with a pool.

This Florida City apartment offers a resort-style backyard with a private heated saltwater swimming pool, a spa, a full soccer field, and beach volleyball, making it an ideal pool getaway.
Spanning 2,350 sq ft, this family-friendly home accommodates up to 14 guests with a fully equipped kitchen, indoor entertainment including a pool table, and is conveniently located 10 minutes from Everglades National Park and 40-50 minutes from Miami's beaches.

This 1-bedroom, 2-bathroom apartment in Marathon Key's Ocean Isles Fishing Village offers direct Atlantic Ocean proximity and views of VACA Cut boat traffic and the Sombrero Light House.
Enjoy access to Marathon's largest swimming pool with on-site fishing, paddle boarding, kayaking, and tiki huts, perfect for a family getaway with a pool.

This oceanfront suite in Tavernier, Florida Keys, is located between Key Largo and Islamorada, offering convenient access to Jimmy Johnson's Big Chill and Mangrove Marina, just a short drive from John Pennekamp Coral Reef State Park.
Enjoy this family-friendly 550 sq ft apartment with a full kitchen, living room, and patio, perfect for up to 4 guests, complete with a swimming pool, hot tub, and private resort beach for an ideal pool getaway.

Enjoy a private swimming pool and a fully fenced backyard in this 3-bedroom, 2-bathroom apartment, perfect for families and pet owners, located just under 10 minutes from Sombrero Beach in Marathon.
Explore Marathon with provided bikes and discover extensive outdoor living spaces including a Tiki bar and gas grill, all within an hour's drive of Key West and Dry Tortugas.

Just a 10-minute walk from Coco Plum Beach, this apartment in Marathon offers proximity to water activities, located 1.4 miles from A Deep Blue Dive Center.
This 400 sq ft apartment with a pool accommodates up to 7 guests, featuring air conditioning, a full kitchen with a dishwasher, and a terrace for enjoying the outdoors.

This Cudjoe Key holiday home is located 21 miles from Key West International Airport and approximately 24 miles from the Ernest Hemingway Home and Museum and Duval Street.
Enjoy this family-friendly two-bedroom, two-bathroom house with a sofa bed, offering 840 square feet of living space and accommodating up to 11 guests, complete with a swimming pool and a hot tub for your enjoyment.

Castaway Island bungalow offers a tropical retreat in Islamorada, Village of Islands, just 500 feet from the captivating waters.
This well-restored 2-bedroom, 1-bathroom bungalow sleeps up to 5 adults and features a swimming pool, jacuzzi, and spa for a superior vacation experience.

Centrally located in Marathon, this apartment is just 3.6 miles from Coco Plum Beach and 3.9 miles from Sombrero Beach, offering easy access to the Florida Keys and within a 1-hour drive of Key West and Key Largo.
This 1160 sq ft apartment accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a private above-ground swimming pool and a tiki bar, perfect for a relaxing getaway with a pool.

Located on Summerland Key, this cottage offers a tranquil Keys experience approximately 20 miles from Key West's attractions.
Enjoy this 790 square foot cottage with 2 bedrooms, sleeping up to 4 guests, complete with a swimming pool and a fully equipped kitchen.

Located within the secure, gated Kawama Yacht Club in Key Largo, this fourth-story apartment offers ocean vistas and is conveniently situated just 1 mile from John Pennekamp Coral Reef State Park.
This renovated, 1190 square foot apartment sleeps 8 and features a modern kitchen, air conditioning, and a private balcony, all within a community with a swimming pool and direct ocean access.

Waterfront canal-side apartment in Marathon, located just a short distance from Captain Hooks Marina and Dive Center and Florida Keys Country Club, offers a recently remodeled half duplex with hurricane impact windows and dockage for boats up to 30ft.
This dog-friendly accommodation features a private heated swimming pool, an open floor plan with a king pull-out sofa bed, and a master suite with an en-suite bathroom, perfect for guests seeking a getaway with a pool.

Directly on a private beach in Islamorada, Village of Islands, this apartment is just 0.3 miles from Windley Key Fossil Reef Geological State Park and San Pedro Underwater Archaeological Preserve State Park.
This pet-friendly apartment, offering 387 sq. ft of space for up to 4 guests, features a heated outdoor swimming pool with ocean views, complimentary Wi-Fi, and on-site activities like kayak and paddleboard rentals.