Compare Vacation Rentals with Pools in Florida Keys, FL

Located in the exclusive Angler's Reef gated community in Islamorada, this apartment is just 500 feet from a private beach and near Hurricane Monument and Indian Key Historic State Park.
This family-friendly apartment with 2 bedrooms and 2 bathrooms accommodates up to 6 guests and features a heated community swimming pool overlooking the ocean, complimentary kayaks, and paddleboards for a perfect pool getaway.

Offering panoramic Atlantic Ocean views, this waterfront condo in Tavernier is located midway between Key Largo and Islamorada, providing convenient access to the History of Diving Museum and world-class diving and snorkeling.
This 910 square foot, two-bedroom, two-bathroom penthouse unit accommodates up to 6 guests and features a Junior Olympic swimming pool, hot tub, private sandy beach, and onsite marina, perfect for a getaway with a pool.

Directly on the beach in Marathon, Florida, Tranquility Bay Resort is a resort offering easy access to Crane Point Museums & Nature Center, just a 3-minute drive away, and Curry Hammock State Park, 13 miles away.
This resort features three swimming pools, including an adult-only and a heated children's pool, alongside water sports like kayaking and paddle boarding for a perfect pool getaway.

Directly on the beachfront in Key Largo, this apartment is situated just 4.1 miles from John Pennekamp State Park and Dolphin Cove, offering direct access to a private beach area and dry boat parking across from Molasses Marina.
This family-friendly, 1320 square foot apartment features 2 bedrooms, 2 bathrooms, and accommodates up to 9 guests, boasting sea views from its balcony, a fenced swimming pool with pool views, a kids pool, playground, tennis court, and free WiFi.

This apartment on Duck Key in Marathon offers a true Keys escape, conveniently located about an hour's drive from Key West and Key Largo, and close to Marathon's cultural sites like the Marathon Air Museum.
Enjoy this 900 square foot apartment with a private dip pool, accommodating up to 6 guests with 2 bedrooms and 2 en-suite bathrooms, all while being just 9.0 miles from Coco Plum Beach and 12.7 miles from Sombrero Beach.

Just 500 feet from Alligator Reef, this Islamorada resort offers a prime location near Miss Islamorada Fishing Charters and a 30-minute drive to John Pennekamp Coral Reef State Park.
Enjoy oceanfront relaxation with a freshwater swimming pool, private beach access, and accommodations featuring full kitchens and private terraces with ocean views at this pet-friendly resort with a pool.

Oceanfront condo in Tavernier, South Key Largo, is located within the guarded Ocean Pointe Suites, just 10 miles from John Pennekamp Coral Reef State Park and 1.7 miles from the Wild Bird Center.
This 840 square foot apartment offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, featuring direct ocean views, a well-equipped kitchen, and access to a heated junior Olympic swimming pool and jacuzzi for a perfect pool getaway.

Directly on the water in Summerland Key, this apartment offers proximity to Florida Keys Beaches, Bahia Honda State Park, Blue Hole, and Big Munson Island.
Enjoy this 740 sq ft apartment with a swimming pool, perfect for up to 4 guests, featuring a kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.

Directly across the open water in Cudjoe Key, this apartment offers spectacular sunrise views and ocean breezes within the oceanfront Venture Out Community, located 30 minutes from Duval Street in Key West.
This newly remodeled apartment accommodates up to 4 guests and features a large screened porch with water views, a heated swimming pool, hot tub, tennis courts, and provided kayaks and bikes, making it an ideal pool 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.

Just two houses from ocean access with a picnic area, this apartment in Marathon offers ocean views from a private balcony and is under a 5-minute drive to Sombrero Beach.
This family-friendly apartment features a private saltwater swimming pool with optional heating, 1100 square feet of living space, and capacity for 8 guests, perfect for your pool getaway in Marathon.

Cheeca Lodge & Spa is a resort located in Islamorada, Village of Islands, Florida, offering 1000 feet of private waterfront with Downtown Key Largo 20 miles away and Long Key State Park 13.7 miles distant.
This luxurious resort features adult and family swimming pools, a 9-hole par 3 golf course, a 525-foot fishing pier, and a full-service watersports facility, ensuring a memorable stay with a pool.

Enjoy direct waterfront access with 30 feet of private dockage on a 100-foot wide canal in Key Colony Beach, offering quick boat access to the ocean and Gulf, and just a 5-minute walk to the Private Cabana Ocean Beach Club with its ocean-view pool and beach.
This 720 square foot, pet-friendly apartment accommodates up to 4 guests and features a fully equipped kitchen, air conditioning, and offers free WiFi, making it an excellent choice for fishing and snorkeling enthusiasts looking for a getaway with a pool.

Located in the Futura Yacht Club community at mile marker 88.5 on the bay side of Islamorada, this 850 square foot apartment is situated in Tavernier, just 500 feet from waterfront attractions like Jimmy Johnson's Big Chill and the Florida Keys Dive Center.
This family-friendly apartment offers a swimming pool, air conditioning, a full kitchen, and accommodates up to 6 guests, with easy access to John Pennekamp Coral Reef State Park and opportunities for jet skiing and kayaking.

Enjoy sea views from this house in Big Pine Key, located 19 miles from Seven Mile Bridge and 25 miles from Florida Keys Aquarium Encounters.
This family-friendly house with a pool offers a grill, free WiFi, and is perfect for fishing and hiking enthusiasts, with dive centers nearby.

Enjoy direct beach access and an outdoor swimming pool at this family-friendly apartment in Key Largo, located 4.4 miles from John Pennekamp State Park and 4.6 miles from Dolphin Cove.
This apartment features a fully equipped kitchen, free WiFi, and a balcony, plus on-site tennis and pickleball courts and complimentary bicycles for exploring the area.

Directly on the oceanfront in Key Colony Beach, this apartment offers prime access to a private sandy beach and is adjacent to Sunset Park, known for its Florida Keys sunset views.
This newly renovated studio apartment sleeps up to four guests and features a fully equipped kitchen, a modern bathroom with a walk-in shower, and access to a heated swimming pool just steps away, perfect for a poolgetaway.com stay.

Just 500 feet from Mangrove Marina, this 4th-floor apartment in Tavernier offers a newly renovated coastal design with easy access to John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park.
This family-friendly apartment, perfect for up to 6 guests, features 850 square feet of living space, a well-equipped kitchen, air conditioning, and a fantastic swimming pool for your enjoyment.

Directly on the oceanfront in Tavernier, this apartment is just 1 mile from the Hurricane Monument and Caribbean Club Bar, and close to John Pennekamp Coral Reef State Park.
This 820 sq ft apartment sleeps up to 7 guests and features 2 bedrooms and 2 bathrooms, offering a swimming pool, jacuzzi, and a garden for a complete pool getaway experience.

Located in Rock Harbor, Key Largo, this oceanfront condo offers direct access to a 200-foot ocean pier and is situated near the Caribbean Club Bar and Christ of the Abyss, with Bluefin Rock Harbor Marina just a short distance away.
This 1370 sq ft apartment, featuring 2 bedrooms and accommodating up to 6 guests, boasts a luxurious interior with marble floors and cathedral ceilings, and provides access to resort amenities including a large oceanfront swimming pool, Jacuzzi, and tennis courts.

Experience ocean and sunrise views from this top-floor apartment in Tavernier, perfectly situated between Key Largo and Islamorada, just miles from John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park.
This family-friendly apartment offers 850 square feet of living space for up to 6 guests, featuring a fully equipped kitchen, air conditioning, and resort-style amenities including a junior Olympic-size swimming pool and a large outdoor jacuzzi for an unforgettable pool getaway.

Prime waterfront location in Marathon Shores offers direct boating access to the Gulf and Ocean via Vaca Cut, featuring a private dock, fish cleaning station, and optional heated swimming pool for year-round enjoyment.
This 1500 sq ft apartment accommodates up to 6 guests with 2 bedrooms and 3 bathrooms, boasting a well-equipped kitchen, central air conditioning, and a dedicated storage room for fishing gear, all secured with outdoor cameras.

Just minutes from Looe Key Reef and Bahia Honda State Park on Summerland Key, this apartment offers prime access for diving and state park exploration.
Enjoy this pet-friendly, 3-bedroom apartment with 660 sq. ft. of living space, a kitchen, and complimentary kayaks, paddleboards, and bikes, all complemented by a year-round heated outdoor swimming pool.

This apartment offers a unique resort experience with a swimming pool and hot tub, located within the Sugarloaf Key / Key West KOA Resort campground, just a 20 to 30 minute drive from Key West's attractions. Enjoy a tropical setting with a private deck, full kitchen, and convenient in-unit laundry, plus on-site recreation rentals like kayaks and paddleboards, all while being a pet-friendly option with a dedicated dog park.

Enjoy waterfront relaxation on Summerland Key, just minutes from Looe Key Reef diving and Bahia Honda State Park, offering complimentary kayaks, paddleboards, and bikes.
This family-friendly apartment, perfect for up to 6 guests, features a shared, heated swimming pool open year-round and welcomes dogs with an additional nightly charge.

Just 500 feet from Florida Keys Beaches and Coupon Bight Aquatic Preserve, this waterfront apartment in Summerland Key offers canal views.
This 860 sq ft apartment with a pool accommodates up to 6 guests and features a 45' seawall dock with extensive boating amenities, a fully equipped kitchen, and 2 bedrooms, perfect for a getaway with a pool.

Enjoy prime waterfront living in Venture Out on Cudjoe Key, offering direct boating access and located just 19 miles from Key West.
This 860 sq ft apartment accommodates up to 6 guests and features a heated swimming pool, Jacuzzi, and tennis court, perfect for a getaway with a pool.

Baker's Cay Resort Key Largo, a resort on the Gulf of Mexico, is conveniently located 11 miles from John Pennekamp National Marine Sanctuary and a 21-mile drive from Theater of the Sea.
This resort offers direct private beach access and features two outdoor swimming pools, providing a perfect getaway with a pool for water sports enthusiasts and families alike.

Directly on the beach in Islamorada's city center, this apartment is just a short walk to the History of Diving Museum and Keys History & Discovery Center, offering a prime location for exploring local culture and history.
This pet-friendly apartment, accommodating up to 8 guests, features 2 bedrooms and 2 bathrooms, with a heated swimming pool offering ocean views, complimentary daily continental breakfast, and on-site rentals for kayaks and paddleboards.