Compare Vacation Rentals with Pools in Key West, FL

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.

Centrally located in Old Town Key West within the gated Duval Square community on Duval Street, this house is walking distance to restaurants, bars, shopping, and entertainment, and a short bike ride to the beaches.
This two-bedroom, 1220 square foot house accommodates up to six guests and features a shared swimming pool, a private balcony off the master bedroom, and a well-stocked kitchen, perfect for a Key West getaway with a pool.

This Key West vacation home sits in the southernmost part of the island, a 4-minute walk from South Beach and 1.9 miles from Key West International Airport.
Enjoy a family-friendly oasis with a heated swimming pool, air conditioning, free WiFi, and a fully equipped kitchen, perfect for up to 7 guests across 900 square feet with 2 bedrooms and 2 bathrooms.

This three-bedroom condo is located in Beachside Key West, offering convenient access to Duval Street attractions via a daily shuttle service.
Enjoy a relaxing stay with this apartment featuring a swimming pool and a private balcony, perfect for families with a guest capacity of eight and offering on-site bike and watercraft rentals.

Directly on a private beach, this historic 1920s resort in Key West is a 7-minute drive from Duval Street and offers two oceanfront swimming pools with direct ocean views.
Enjoy a range of amenities including a spa, fitness center, on-site dining, and convenient access to water sports and nearby attractions like Fort Zachary Taylor Historic State Park.

Enjoy expansive waterfront views from this luxurious 4-bedroom apartment in Key West's tranquil Key Cove Landings neighborhood, offering a quiet retreat just a short walk to Publix and the island's largest shopping center, and a short drive from Southernmost Point and the Ernest Hemingway Home and Museum.
This spacious 2360 sq ft apartment accommodates up to 8 guests and features a private, heated swimming pool, a gourmet kitchen, and off-street parking, making it an ideal pool getaway.

Located in Old Town Key West, this apartment is just a block from Duval Street and the Ernest Hemingway Home and Museum, and 0.5 miles from the Southernmost Point.
This dog-friendly 750 square foot apartment offers a shared swimming pool and courtyard, air conditioning, free Wi-Fi, and parking, accommodating up to 4 guests.

Prime waterfront condo in Key West's Meadows district, just 1 mile from Duval Street and the Historic Seaport, offers direct access to Garrison Bight Marina.
This spacious 2-bedroom, 2-bathroom apartment with a private balcony sleeps up to 8 guests and features a heated swimming pool, private boat slip, and is pet-friendly for dogs up to 25 lbs.