Compare Vacation Rentals with Pools in Key West, FL

Just a block from Duval Street and the Atlantic Ocean, Santa Maria Suites Resort in Key West offers an excellent location, placing you an 11-minute walk from the Ernest Hemingway House.
This all-suite resort features two outdoor heated swimming pools set in lush gardens, providing a perfect escape with complimentary happy hour and in-suite laundry facilities.

This Old Town Key West house is located on the 1000 block of Duval Street, offering a 10-minute walk to Duval Square's dining and attractions, with the Southernmost Point just a short stroll away.
Enjoy a private deck, balcony, and access to a rooftop swimming pool, perfect for soaking up the Key West sunshine, with parking available in a private garage and an in-unit washer/dryer for your convenience.

Located on the east side of Key West within the Sunrise Suites community, this apartment is a mile from the beach and a 10-minute drive to Duval Street.
Enjoy stunning sunset views from a private balcony at this beautifully updated 2-bedroom condo with a shared heated swimming pool and hot tub, perfect for your Key West getaway.

Located in Key West's historic Bahama Village, this studio is just 500 feet from Duval Street, the Southernmost Point, and the Ernest Hemingway Home.
Enjoy a relaxing stay in this pet-friendly studio with a heated swimming pool, kitchenette, and complimentary WiFi, perfect for travelers seeking a getaway with a pool.

Directly on the Atlantic Ocean in Key West's Beachside neighborhood, this apartment is adjacent to Smathers Beach and less than a 5-minute drive from historic landmarks like the Southernmost Point and Ernest Hemingway Home and Museum.
This 2-bedroom, 2-bathroom apartment sleeps 4 and offers a premium stay with an Olympic-size heated swimming pool, a 20-person Jacuzzi, sauna, tennis courts, and secure parking, perfect for a getaway with a pool.

This house in Key West offers a prime location, situated just 400 yards from the city center and a 13-minute walk from Mallory Dock and 0.7 miles from Mallory Square.
Enjoy this 680 square feet house with a swimming pool, perfect for families of up to 4 guests, featuring air conditioning, a full kitchen, and complimentary Wi-Fi, with opportunities for cycling nearby.

Just 500 feet from local landmarks, this Key West manor house offers convenient access to the area's attractions in a prime district.
Enjoy a relaxing stay with complimentary WiFi, a garden, and on-site laundry, all complemented by a refreshing swimming pool perfect for your getaway.

Enjoy expansive water views from this waterfront apartment in the private Key Cove Landings community, located within walking distance to the island's largest shopping center and a Publix grocery store, and just 1.2 miles from Fort Zachary Taylor Historic State Park.
This exceptional Key West apartment offers a private heated pool, a chef's kitchen with gourmet appliances, and four bedrooms, perfect for a luxurious getaway with a pool.

Located in the Key West Historic District, this apartment is half a block from Duval Street and within walking distance of Mallory Square and the Historic Seaport.
This historic apartment offers a pet-friendly stay with air conditioning, internet, and a swimming pool, perfect for a getaway with its second-floor rooms and shared wrap-around porches.

Located in Old Town Key West, this apartment is just steps from the beaches and Duval Street, offering a prime location in a historic district.
This 1320 sq ft apartment features 2 bedrooms and 2 bathrooms, sleeping up to 6 guests, and boasts a private outdoor oasis with a heated swimming pool, gas grill, and wet bar, perfect for a 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.

Located in historic Bahama Village, this second-floor micro-efficiency apartment is just a few blocks from Duval Street, the Key West Lighthouse, and the Ernest Hemingway Museum.
This pet-friendly apartment offers access to a heated swimming pool, a grill, and a sundeck, perfect for a getaway with your furry friend.

Directly on Garrison Bight Marina, this waterfront apartment in Key West's Meadows neighborhood is just 1 mile from Duval Street and the Historic Seaport.
This spacious 1,190 sq ft apartment offers a private boat slip, direct stair access to a heated swimming pool with a tiki area and BBQ grills, and is pet-friendly with free on-site parking.

Just 1,500 feet from Southernmost Point and the Ernest Hemingway Home and Museum, this secluded Old Town Key West cottage offers a private gated entrance and a tropical oasis.
This 3-bedroom, 2-bathroom apartment for 6 guests features a private swimming pool with optional heating, a covered porch with a swing, a side yard with a grill, and a master suite with a private outdoor shower, perfect for a getaway with a pool.

Located in downtown Key West's desirable Pelican Landing community, this waterfront corner condo is approximately 1 mile from Duval Street and 10 minutes from the Key West Airport.
This spacious 1,350 sq ft apartment offers direct stair access to a heated community swimming pool and sleeps up to 8 guests, featuring a private balcony with marina and pool views, a private boat slip, and is pet-friendly for one dog up to 25 lbs.