Compare Vacation Rentals with Pools in Key West, FL

House. You will be based in Key West.
Services and facilities include a fridge, air conditioning and a kitchen.

This apartment offers a prime location in the historic old town of Santa Maria, just two blocks from Duval Street and two blocks from the beach.
Enjoy this 1000 sq ft, two-story apartment with a pool, featuring two bedrooms, 2.5 bathrooms, a full kitchen, and private balconies, accommodating up to six guests with a fitness center and parking.

Directly on the Atlantic Ocean in Key West, this recently renovated top-floor apartment offers stunning ocean and courtyard views, just steps from the water.
This spacious 1400 sq ft apartment with a pool sleeps six and features a private balcony, a fully equipped kitchen with stainless steel appliances, and a master suite with a custom walk-in shower and separate tub, perfect for a memorable getaway.

Perfectly situated in Key West's Old Town, this resort offers direct access to a private beach and is just a 1-minute walk from the Duval Street entertainment district, with the historic Hemingway Home and Museum only a 5-minute drive away.
This resort features a swimming pool with waterfront views and provides a full-service spa, on-site dining at One Duval, and easy access to water sports for a complete getaway.

Enjoy a prime Key West location, just 0.6 miles from Simonton Street Beach and Duval Street, and within a short walk to the Ernest Hemingway Home and Museum and Key West Aquarium.
This apartment offers a private entrance, city-view balcony, fully equipped kitchen, and access to a swimming pool, perfect for a comfortable stay with a pool.

Located in Stock Island, this luxurious boat offers a premium marina experience with convenient access to local dining and attractions.
This boat accommodation features 4 bedrooms, 4 bathrooms, and sleeps 8 guests, boasting a private swimming pool alongside exceptional amenities including air conditioning, internet, and a full kitchen.

Located in Stock Island, this house is a short drive from Key West's main attractions, with the airport 3.1 miles away and Duval Street 5.6 miles distant.
This spacious four-bedroom, five-bathroom holiday home offers ample room for ten guests and features a private dock, an outdoor swimming pool, a fitness room, and free on-site private parking.

This 1BR condo is located in Historic Key West, just a short walk from Duval Street, dining, nightlife, and beaches.
Enjoy this Key West apartment with a pool, offering comfortable sleeping for up to 6 guests and a fully equipped kitchen for convenient meal preparation.

This spacious waterfront penthouse in downtown Key West is located approximately 1 mile from Duval Street and the Historic Seaport, and just 0.4 miles from Fausto's Food Palace.
Enjoy this 2,000 sq ft apartment with a private boat slip and a heated swimming pool, perfect for accommodating up to 16 guests with a pet-friendly policy for one dog under 25 lbs.

Just a 4-minute walk from Smathers Beach, this vacation home is located 1.6 miles south of the Southernmost Point and within 2.1 miles of Duval Street and the Ernest Hemingway Home and Museum.
This family-friendly house offers a relaxing stay with air conditioning, a fully equipped kitchen, and a swimming pool, alongside amenities like a sauna, jacuzzi, and private parking.

Enjoy a tropical oasis in Key West, just a short distance from Duval Street's attractions, offering effortless walkability and access to bike rentals and scooters for easy exploration. This spacious two-bedroom, two-bathroom apartment, perfect for families and pet owners, features two private balconies and a shared backyard with a swimming pool, dining area, and grill.

Located in Key West's Windsor Lane area, this townhome is just 500 feet from Mallory Square's Sunset Celebration and a short distance from the Historic District, Seaport, and Southernmost Point Buoy.
This family-friendly house with a pool offers 3 bedrooms, sleeps 8, and features a private heated swimming pool, a fully equipped kitchen, free high-speed WiFi, and a well-behaved pet welcome.

This waterfront penthouse apartment in downtown Key West offers stunning marina views and is located approximately 1 mile from Duval Street and the Historic Seaport.
Enjoy a spacious 2,200 sq ft layout perfect for up to 16 guests, featuring 4 bedrooms, 4 bathrooms, a loft, and access to a heated community swimming pool with a tiki area and BBQ grills, all pet-friendly for one dog up to 25 lbs.

Located in the southernmost district of Key West, this house is just a short walk from Duval Street and the iconic Southernmost Point buoy.
This family-friendly house offers 4 bedrooms, 3 bathrooms, and a guest capacity of 10, featuring a swimming pool for your enjoyment.

Just an 8-minute walk from the Key West Tropical Forest and 2.5 miles from Key West International Airport, this house offers convenient access to the Ernest Hemingway Home and Museum, Duval Street, and Southernmost Point, all within 5 miles.
This family-friendly 2-bedroom house, featuring 840 square feet and accommodations for 4 guests, includes air conditioning, free WiFi, a kitchen with a fridge and microwave, and a private garden with a swimming pool for your enjoyment.

Just 500 feet from Duval Street in Key West's Old Town, this house offers a prime location for exploring the island, just 4 blocks from the Atlantic Ocean.
This family-friendly Key West house features a private swimming pool with lounge chairs, a fully equipped kitchen, air conditioning, and accommodates up to 6 guests, making it an ideal getaway with a pool.

Enjoy unobstructed marina and pool views from this second-floor corner apartment in Key West's Pelican Landing community, located just 1 mile from Duval Street and the Historic Seaport.
This pet-friendly apartment offers 2 bedrooms, 2 bathrooms, sleeps 8, and features a private balcony with pool access, a fully equipped kitchen, and a heated community swimming pool perfect for your pool getaway.

Just 7 minutes on foot from Duval Street and a 6-minute walk to the Ernest Hemingway Home and Museum, this Key West house is perfectly situated for exploring the island.
This Key West house offers a private swimming pool, a spa, and fitness center, and accommodates up to 7 guests with 480 square feet of living space, a full kitchen, and air conditioning.

Located in Key West's downtown waterfront area, this house is 1.3 miles from Southernmost Point and 1.5 miles from Key West Aquarium, offering sea views and outdoor seating.
This 1190 square foot vacation home with 2 bedrooms and 2 bathrooms is perfect for up to 14 guests, featuring a private swimming pool, a fully equipped kitchen, and on-site dock access.

Located in Bahama Village, this apartment is just a few blocks from Duval Street, placing you within walking distance of the Ernest Hemingway Home and the Southernmost Point.
This 140 square feet apartment offers a queen bed, a kitchenette with a microwave and mini-fridge, and access to a heated swimming pool, sundeck with BBQ, and laundry facilities, perfect for up to 2 guests seeking a Key West getaway with a pool.

Just 1500 feet from South Beach and 1800 feet from Southernmost Point, this apartment in Key West offers an ideal location within walking distance of Duval Street and the Ernest Hemingway Home and Museum.
This apartment, perfect for up to 7 guests, features 2 bedrooms and includes a swimming pool for a complete getaway experience.

Directly located at the Stock Island Marina, The Perry Hotel & Marina Key West offers exceptional waterfront views and marina access, just one bridge away from Key West's attractions and 5 miles from Duval Street.
This resort boasts luxury accommodations with private balconies, two on-site sea-to-table restaurants, and two waterfront swimming pools, perfect for a relaxing getaway with a pool.

Prime waterfront condo in Key West's Meadows district, offering direct dock access at Garrison Bight Marina and a short 1 mile walk to Duval Street.
This 1300 sq ft, 2-bedroom, 2-bathroom apartment includes a private balcony with pool and marina views, full-size in-unit laundry, and community amenities including a heated swimming pool, tiki area with grills, and on-site parking, perfect for boaters and families with a capacity of 8 guests.

Waterfront penthouse in downtown Key West, this apartment offers spectacular marina and sunset views, located approximately 1 mile from Duval Street and the Historic Seaport.
This spacious, pet-friendly apartment with 4 bedrooms and 4 bathrooms accommodates up to 15 guests and features a fully equipped kitchen, elevator access, and a heated community swimming pool with a tiki area and BBQ grills.