Compare Vacation Rentals with Pools in Florida Keys, FL

This Duck Key townhouse offers a private patio with a plunge pool, perfect for relaxation and enjoying the tropical landscape, located just 0.3 miles from Angler and Ale restaurant and Dolphin Connection.
With 900 square feet, this family-friendly house accommodates up to 4 guests and features 2 bedrooms, a fully equipped modern kitchen, high-speed internet, and air conditioning, ensuring a comfortable stay with a pool.

Ocean Pointe Suites in Tavernier offers a tropical setting with ocean views, providing a Caribbean ambiance just steps from the beach and marina.
This 2-bedroom, 2-bathroom condo accommodates up to 6 guests and features a heated swimming pool, a 15-person hot tub, tennis courts, and 24-hour gated security for a complete getaway.

Centrally located in Marathon, this cabin is just 0.6 miles from Curry Hammock State Park and within 3 miles of Sunset Park Beach and Coco Plum Beach.
Enjoy your stay at this cabin with a pool, offering air conditioning, free WiFi, and complimentary bicycles for exploring the area.

Located in Homestead, this vacation home is 3.8 miles from Florida Keys Factory Shops and 5.3 miles from Homestead Miami Speedway.
This family-friendly house offers 1850 square feet of space for 19 guests, featuring 4 bedrooms, 3 bathrooms, a private heated swimming pool, and an on-site bar.

Direct canal access to the Atlantic Ocean makes this Cudjoe Key house ideal for fishing enthusiasts, offering a tranquil environment for a relaxing family vacation with a swimming pool.
This 1-bedroom, 1.5-bathroom house accommodates up to 6 guests and features a screened lanai with canal views, a 35 ft seawall for boaters, and is equipped with a fridge, microwave, and dishwasher.

This apartment in Ocean Pointe Suites, Tavernier, is an end unit offering added privacy and natural light, just a short drive from Key Largo and Islamorada.
Enjoy this 2-bedroom, 2-bathroom apartment with a king bed in the master and two twin beds in the guest room, perfect for up to 5 guests, featuring a full kitchen and access to a swimming pool, Jacuzzi, and garden.

Prime waterfront condo in Key Largo offers direct access to a private marina and overlooks a saltwater lagoon and a heated swimming pool.
This 2-bedroom, 2-bathroom apartment accommodates up to 7 guests and features resort-style amenities including on-site pickleball and tennis courts.

Keys Bohemian at Ocean Pointe 1312 is a newly renovated condo in Tavernier, Florida, offering a bohemian-inspired ambiance and a tranquil getaway within the Ocean Pointe community, just 500 feet from local attractions.
This apartment features 2 bedrooms and 2 bathrooms, accommodating up to 6 guests, and boasts a swimming pool, jacuzzi, garden, and parking, making it ideal for families and couples seeking a relaxing escape with a pool.

Located less than 1 mile from Key Colony Beach, this resort in Marathon is also within 5 miles of Sombrero Beach and the Dolphin Research Center.
This Fairfield Inn & Suites offers two outdoor swimming pools, on-site snorkeling, and boat or kayak rentals, perfect for a getaway with a pool.

Directly on the water in Cudjoe Key's secure Venture Out community, this apartment is just 20 minutes from Key West and 5 miles from the world-class Looe Key reef dive site.
This pet-friendly, family-friendly apartment with 2 bedrooms and 1 bathroom sleeps 6 and offers direct waterfront access with a seawall, a heated swimming pool, hot tub, kayaks, and bikes for exploring the Florida Keys.

This spacious resort-style apartment in Homestead's Redlands offers a tranquil escape, surrounded by fruit trees and greenery, providing a peaceful residential experience just a short drive from local attractions.
Enjoy extensive backyard amenities at this family-friendly apartment with a heated swimming pool, a children's playground, a multi-sport court, and a dedicated entertainment garage featuring a movie theater and game room, perfect for groups of up to 16 guests.

Experience a unique farm stay in a rural area of Homestead, Florida, just a short drive from Miami and the Florida Keys, offering proximity to attractions like the Coral Castle Museum and Homestead Miami Speedway.
This spacious farm property accommodates up to 11 guests with 4 bedrooms and 3 bathrooms, featuring a refreshing private swimming pool, a fully equipped kitchen, air conditioning, and opportunities to interact with farm animals.

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.

Oceanfront villas in Islamorada offer direct access to a private beach and a saltwater lagoon, located just 4.7 miles from John Pennekamp State Park and 4.8 miles from Dolphin Cove.
This recently renovated 2-bedroom, 2-bathroom villa provides 1100 square feet of living space with a balcony and ocean views, perfect for families seeking a getaway with a pool, complimentary WiFi, and proximity to local attractions.

Steps from The Turtle Hospital and Shady Palm Art Gallery, Tranquility Bay Resort offers a prime beachfront location in Marathon, just a 10-minute drive from Sombrero Beach and Boot Key Harbor.
This resort features three outdoor swimming pools, a private beach, on-site dining at TJs Tiki Bar, and provides a family-friendly stay with internet and a fitness center.

Directly across from John Pennekamp National Underwater Park, this Key Largo apartment is within the exclusive Kawama Yacht Club, offering direct access to a private oceanfront beach and a saltwater lagoon.
This family-friendly apartment with a pool sleeps up to four guests and features a kitchen with a fridge, microwave, and dishwasher, plus a balcony with lagoon views and proximity to extensive water activities.

Oceanfront, this cottage in Summerland Key is located 20 miles from Key West, offering direct dock and seawall access, and is just steps from an on-site swimming pool for your enjoyment.
This 390 sq ft cottage with a full kitchen, queen bedroom, and screened patio accommodates 2 guests and is conveniently near Florida Keys Beaches, Coupon Bight Aquatic Preserve, Blue Hole, and Looe Key National Marine Sanctuary.

Steps from a saltwater lagoon and swimming pool, this two-story apartment in Key Largo offers direct access to a 3-acre lagoon perfect for swimming, snorkeling, and kayaking.
This pet-friendly apartment features 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests, including a golf cart for exploring the area and on-site tennis/pickleball courts.

Holiday Inn Key Largo is located in Key Largo, just 3.2 miles from John Pennekamp State Park and a 4-minute drive from Dolphin Plus Bayside.
This resort offers a relaxing getaway with two swimming pools, including one with a waterfall, and a hot tub, perfect for travelers seeking a pool getaway.

This 3-bedroom house in Marathon offers a private 6-acre resort within the Coral Lagoon Marina community, featuring direct Gulf access via a private 34' boat slip just 10 minutes to open water through Vaca Cut.
Enjoy 1420 square feet of living space with a capacity for 8 guests, complete with a gourmet kitchen, air conditioning, and access to a heated saltwater community swimming pool, perfect for those seeking a 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.

This Redlands Retreat is located in the B and L Farms Airport area, 5 miles from Fruit Spice Park and 11 miles from Coral Castle.
Enjoy this house with a pool, offering 1 bedroom and 3 bathrooms, accommodating up to 28 guests with a private swimming pool, kitchenette, air conditioning, and free WiFi.

Located within Country Walk, this apartment offers convenient access to local attractions and amenities, just 500 feet from the nearest shopping center.
This 5-bedroom, 3-bathroom apartment accommodates up to 12 guests and features a private, heated swimming pool perfect for year-round enjoyment, alongside spacious social areas with a pool table and an outdoor barbecue grill.

Smuggler's Cove #414 is a canal-front apartment located within the secure Venture Out community on Cudjoe Key, offering excellent access to the Lower Keys' attractions and featuring a 23' seawall with dockside water perfect for boaters.
This pet-friendly apartment provides a comfortable island-inspired interior with modern conveniences, including Smart TVs and an in-unit washer/dryer, and guests can enjoy the community's swimming pool, marina, lagoon, and sports courts for a complete getaway with a pool.