Compare Vacation Rentals with Pools in Key West, FL

Directly on Garrison Bight Marina, this waterfront apartment offers a private boat slip and is located just 1 mile from Duval Street and downtown Key West attractions.
This spacious 2-bedroom, 2-bath condo sleeps 8 guests and features a heated swimming pool with a tiki area, BBQ grills, and direct balcony access to the pool and docks, all pet-friendly for dogs up to 25 lbs.

Enjoy an apartment with a pool just steps from downtown Key West, a 9-minute walk from South Beach and a 15-minute walk from the Key West Aquarium.
This apartment offers complimentary WiFi, on-site parking, and a garden, perfect for a relaxing stay with easy access to attractions like Duval Street and the Ernest Hemingway Home and Museum.

Enjoying prime Key West location, this apartment is in the Midtown Neighborhood, across from the Atlantic Ocean and just 500 feet from Smathers Beach, with downtown Key West and Duval Street a 10-minute drive or bike ride away.
This family-friendly apartment with 2 bedrooms and 2 bathrooms accommodates up to 6 guests and features a swimming pool, a hot tub, and a newly renovated kitchen, perfect for a getaway.

Located in Key West city center, this studio is an 8-minute walk from South Beach and the Key West Butterfly and Nature Conservatory, offering convenient access to major attractions like the Ernest Hemingway Home and Museum.
Enjoy amenities such as free WiFi, air conditioning, and barbecue facilities at this studio with a pool, perfect for exploring the surrounding area's water sports and landmarks like Southernmost Point and Duval Street.

Just 500 feet from Duval Street, this house in Key West offers prime access to the island's renowned dining, shopping, and nightlife.
This 2-bedroom, 1-bathroom house accommodates up to 6 guests and features exclusive access to two swimming pools, a private porch, and an outdoor bar and grill area perfect for entertaining.

Enjoy a prime waterfront apartment in Key West's Meadows neighborhood, offering marina views and a private balcony, located just 1 mile from Duval Street and 0.4 miles from Fausto’s Food Palace.
This 1,190 sq ft apartment, perfect for up to 6 guests with 2 bedrooms and 2 bathrooms, features a community heated swimming pool, a tiki area, BBQ grills, and a private boat slip, ideal for boating enthusiasts.

Enjoy ocean views from a private balcony just a 4-minute walk from Smathers Beach, placing you 1.6 miles from the Southernmost Point and 2.1 miles from Duval Street.
This 1360 square feet apartment, offering 2 bedrooms and 2 bathrooms, features a fully equipped kitchen, free WiFi, and a swimming pool, ideal for a Key West getaway.

Located within the esteemed Key West Golf Club neighborhood, this townhome offers an island lifestyle just a short drive from the historic Old Town and its attractions.
This newly renovated two-bedroom townhome accommodates up to six guests and features a private swimming pool, perfect for enjoying the Florida sun.

Centrally located in Key West, this apartment offers easy access to local attractions and is less than two miles from the beach.
This two-bedroom apartment with a swimming pool accommodates up to four guests and features a kitchen with a fridge and microwave, plus air conditioning and parking.

Prime waterfront living awaits in Key West's Garrison Bight Marina, just 0.5 miles from the Southernmost Point and Ernest Hemingway Home and Museum, offering direct water views and a private boat slip.
This 1220 sq ft apartment, accommodating up to 6 guests, features 2 bedrooms with en-suite bathrooms, in-unit laundry, parking for two vehicles, and access to a swimming pool for a perfect getaway.

Located in Old Town Key West, this Conch-style apartment is a 10-minute walk from the beach and a 15-minute stroll to Duval Street.
This pet-friendly, two-bedroom apartment boasts 1160 square feet, sleeps up to 9 guests, and offers a tropical backyard with a shared swimming pool, perfect for a pool getaway.

This studio cottage is located in a tranquil residential section of Old Town, Key West, a short walk to numerous attractions.
Enjoy a private and intimate accommodation experience with a swimming pool and air conditioning, perfect for a getaway.

Located in the gated Duval Square community on Duval Street in Old Town Key West, this house is steps from restaurants, bars, shopping, and entertainment, with beaches just a short walk or bike ride away.
This two-bedroom, one-bathroom house accommodates up to six guests and features air conditioning, a kitchen with a fridge, freezer, and dishwasher, private balconies on both levels, and access to a shared swimming pool, offering a perfect getaway with a pool.

Oceanfront penthouse living awaits in Key West, offering direct ocean views from a 60-foot wraparound balcony and convenient elevator access just steps from the beach.
This spacious 2,000 sq. ft. apartment accommodates up to 8 guests and features a king, queen, and two twin beds, along with access to an Olympic-size swimming pool, fitness center, and secure garage parking.

Located in the Meadows neighborhood of Key West, this apartment offers views of Garrison Bight and is just a short distance to Old Town, with the Ernest Hemingway Home and Museum and Southernmost Point nearby.
This spacious 2830 sq ft apartment accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private heated swimming pool, a boat slip, and a chef-inspired kitchen for a perfect getaway with a pool.

Beachside Resort & Residences offers direct access to a private beach with Gulf of Mexico views, located less than 1.2 miles from Key West Airport and providing a free shuttle to Key West city center.
This resort features a swimming pool and a water view fitness center, with accommodations including flat-screen TVs, Bluetooth speakers, and options for full kitchens and balconies, perfect for a Key West getaway with a pool.

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.

Located in the gated Coral Hammock community, this apartment is just minutes from Key West attractions like the Ernest Hemingway Home and Museum and Southernmost Point.
This spacious 1400 sq ft apartment with a pool offers a family-friendly 3-bedroom, 3-bathroom layout and features a full kitchen, air conditioning, and a deck with a grill, providing easy access to the swimming pool, clubhouse, and gym.

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.

Conveniently located just a short ride from Key West International Airport, this apartment offers easy access to downtown Key West's attractions, restaurants, bars, shops, and the Historic Seaport.
This family-friendly apartment, perfect for up to 6 guests, features 2 bedrooms and 2 bathrooms, a chef-ready kitchen, and a private balcony, all complemented by a shared swimming pool with a hot tub, BBQ grills, and tennis courts for your enjoyment.

Located in Key West, this apartment is just 500 feet from Southernmost Point and the Ernest Hemingway Home and Museum, offering convenient access to Smathers Beach and other Florida Keys beaches.
This pet-friendly apartment, featuring a swimming pool, jacuzzi, and terrace, offers 1190 square feet of living space to accommodate up to 6 guests, complete with a full kitchen, air conditioning, and a private parking spot.

Enjoy a waterfront resort experience in Key West, just a 3-minute walk from Duval Street's dining and nightlife.
This resort features a swimming pool and offers on-site spa services, water activities like scuba diving and snorkeling, and two distinct dining options.

Located in Key West's Meadows district, this waterfront apartment is just 1 mile from Duval Street and the Historic Seaport, offering convenient access to Charter Row for boat excursions and situated 0.4 miles from Fausto’s Food Palace.
This spacious 2,000 sq ft, 4-bedroom apartment accommodates up to 16 guests and features dual balconies with marina and sunset views, private dockage, and access to a heated swimming pool, perfect for your pool getaway in Key West.

Located on the east side of Key West within the Sunrise Suites community, this apartment is 1 mile from Smathers Beach and a 10-minute drive to Duval Street.
This 800 square foot apartment, perfect for up to 6 guests, features a modern coastal design, a fully equipped kitchen, and offers access to a shared heated pool and hot tub.

Located in Key West's historic district, this apartment is just one block from Duval Street and within walking distance of Mallory Square and the Historic Seaport.
This property offers a heated swimming pool and accommodates up to 19 guests across 7 units, making it ideal for large groups seeking a getaway with a pool.

Located in Key West, this suite is approximately 4 miles from Southernmost Point and Ernest Hemingway Home and Museum, and just 0.6 miles from Key West International Airport.
This 2-bedroom suite accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, and an outdoor swimming pool perfect for a pool getaway.

Enjoy a sunny Florida Keys experience at this apartment in Key West, located in the Sunrise Suites Resort just 0.6 miles from Southernmost Point and the Ernest Hemingway Home and Museum, and a short distance to Florida Keys Beaches and Smathers Beach.
This 800 square foot apartment, accommodating up to 6 guests, features 2 bedrooms and 2 bathrooms, a private balcony with Salt Ponds Preserve views perfect for birdwatching, and access to a shared swimming pool, hot tub, fitness room, and tennis court, making it an ideal getaway with a pool.

Located on Key West's southeast side, this apartment is 1 mile from Smathers Beach and a 10-minute drive from Duval Street.
Enjoy this 800 square foot apartment with a heated swimming pool, private balcony, and capacity for 6 guests, offering a convenient stay with a pool for your Key West getaway.