Compare Vacation Rentals with Pools in Key West, FL

Enjoy a memorable Key West getaway at this private 2-bedroom, 2-bathroom apartment offering a resort-style experience with a swimming pool, hot tub, and fitness center.
This well-equipped condo sleeps up to 6 guests and features a full kitchen, king-sized beds, free WiFi, and free parking, perfect for families seeking a comfortable stay with excellent amenities.

Offering stunning sunset views, this apartment is located in the Sunrise Suites community on the east side of Key West, approximately one mile from the beach and a 10-minute drive to Duval Street.
This 800 square foot apartment, perfect for up to six guests, features a modern coastal interior with a fully equipped kitchen, a private balcony, and access to a shared heated swimming pool and hot tub.

Located in Prime Old Town Key West on Southard Street, this apartment is steps from Duval Street's dining and bars, and within walking distance to museums and Fort Zachary Taylor beach, which is 1.1 miles away.
This 1190 sq ft apartment with 3 bedrooms and 2 bathrooms accommodates up to 8 guests and features a private 40' heated swimming pool with a grill, a fenced yard, and concierge services.

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.

Just a 9-minute walk from Smathers Beach, this Key West house offers a prime location, situated approximately 2 miles from the iconic Southernmost Point and only 1.2 miles from Key West International Airport.
This 850 square foot house with 2 bedrooms accommodates up to 6 guests and features a refreshing swimming pool, a relaxing hot tub, and a patio with city views, perfect for a getaway with a pool.

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.

Enjoy a private, gated retreat on upper Duval Street in Key West, just steps from abundant dining, shops, and nightlife, and a short distance from the Ernest Hemingway Home and Museum and Southernmost Point.
This 1190 square foot apartment, accommodating up to 6 guests, features 2 bedrooms, 2 bathrooms, a private balcony with a hot tub, and access to a sparkling community swimming pool, offering the perfect getaway with a pool.

Enjoy a fantastic Key West getaway at this house, conveniently located just over a mile from Southernmost Point and the Key West Aquarium, and within 1.4 miles of Mallory Dock and Mallory Square.
This accommodation offers a refreshing swimming pool, a fully equipped kitchen with a dishwasher, and air-conditioned comfort, perfect for exploring attractions like Higgs Beach and Duval Street.

Experience luxury in this expansive 3-bedroom apartment located within the Beachside Resort & Residences, a seven-acre property offering stunning Gulf of Mexico views in Key West.
This resort condo with a pool features a private balcony, a fully-equipped kitchen with stainless steel appliances, and sleeps up to eight guests, providing access to a heated swimming pool, hot tub, fitness center, and on-site dining.

Located in Old Town Key West, this condo offers convenient access to the sea and is just 0.3 miles from the Ernest Hemingway Home and Museum and Southernmost Point.
This 1490 sq ft apartment features 3 bedrooms, 2 bathrooms, and accommodates up to 8 guests, boasting a shared swimming pool with views of Duval Street.

Located in Old Town Key West, this apartment is half a block from Duval Street and close to Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
Enjoy a private heated swimming pool with a waterfall, a gourmet kitchen, and three bedrooms with private baths in this spacious apartment.

Just 500 feet from Duval Street, this Key West cottage is located in The Colony, a secluded, gated enclave offering easy access to Ernest Hemingway Home and Museum and Southernmost Point.
Enjoy this 530 square foot cottage with vaulted ceilings and exposed beams, featuring a private deck and shared access to a large swimming pool, perfect for sunning and relaxing.

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.

Enjoy a Key West apartment getaway with a private balcony overlooking tranquil salt marshes, conveniently located near the Key West airport and offering easy access to local transportation like mokes and scooters.
This family-friendly apartment with a swimming pool accommodates up to 6 guests in 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, central air conditioning, and complimentary parking for one vehicle.

Just 50 feet from your door, a community swimming pool awaits in this Coral Hammock townhome, offering a prime Stock Island location with excellent dining within walking distance and Duval Street a short 10-minute Uber ride away.
This spacious 3-bedroom, 2.5-bath townhome accommodates up to 8 guests and includes a full kitchen, air conditioning, and a garden, making it a family-friendly option with a pool.

This Key West vacation home is located in the historic Old Town district, just 4 blocks from the Atlantic Ocean and 1 block from Duval Street.
Enjoy this 1370 square foot house with a private swimming pool, perfect for a tropical getaway with family or friends, accommodating up to 6 guests.

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.

Located in Key West's Northside Resort neighborhood, this apartment compound is within walking distance of shopping and Publix, and a short drive from the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park.
This 8-bedroom, 7-bathroom apartment offers 4000 square feet of space for up to 16 guests, featuring luxurious master suites, a chef's kitchen, and a private heated swimming pool with a BBQ grill.

Just 150 feet from Duval Street in Old Town Key West, this apartment is located in the front section of Conch Republic Cottages, offering a private, gated escape.
This one-bedroom apartment with a queen sofa bed comfortably sleeps up to four guests and features a spacious porch, updated kitchen with an ice-maker and blender, and access to a shared swimming pool located two blocks away, making it an excellent choice for travelers seeking a getaway with a pool.

This Key West apartment is located in the city center, three miles from Duval Street and one mile from Smathers Beach, offering proximity to the ocean and major landmarks like the Southernmost Point and Ernest Hemingway Home and Museum.
Enjoy 800 square feet of living space with three bedrooms and two bathrooms, accommodating up to six guests, featuring a private balcony, an outdoor spa, a gym, and a swimming pool with a Tennessee court for recreation.

This 3-bedroom townhome in Coral Hammock on Stock Island offers a resort-style community swimming pool, perfect for relaxation, and is just a short walk from waterfront dining and boating activities.
Accommodating up to 11 guests across two floors, this family-friendly apartment features three bathrooms, a full kitchen with a dishwasher, and air conditioning, ensuring a comfortable stay with access to a community gym.

Just 0.6 miles from Key West International Airport, this house is located in Key West, offering convenient access to attractions like the Ernest Hemingway Home and Museum and Duval Street, both within 4.3 miles.
This 780 square foot house with a pool accommodates up to 11 guests and features a private balcony, a well-equipped kitchen, and a relaxing hot tub.

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.

Located in the Casa Marina Neighborhood on the south end of Duval Street, this historic 1930s Conch cottage is just two blocks from Higgs Beach and a short walk to the KW Butterfly & Nature Museum and Southernmost Point.
This pet-friendly apartment offers a private escape with a shared swimming pool, poolside deck with a grill, and private decks for outdoor dining, accommodating up to 10 guests with 3 bedrooms and 2 bathrooms.

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.

Perfectly situated in Old Town Key West, this 3-bedroom, 3-bathroom cottage is just 500 feet from Duval Street, Mallory Square, and attractions like the Southernmost Point and Ernest Hemingway Home and Museum.
This pet-friendly cottage offers the unique option to rent three separate units or the entire property, featuring a shared seasonally heated swimming pool with lounge chairs and outdoor dining areas with grills.

Directly on the Atlantic Ocean, this apartment in Key West's tranquil Mid-Town area is a 5-minute ride to local markets and a short bike ride to Old Town and Duval Street, offering exclusive access to amenities with ocean views, including two swimming pools.
This 5-guest capacity apartment features a fully equipped kitchen, central air conditioning, WiFi, two full bathrooms with spa-like showers, and an in-unit washer/dryer, perfect for a getaway with a pool.

Located in the Key West Historic District, this historic inn is just steps from Duval Street, the Historic Seaport, and attractions like the Mel Fisher Maritime Museum and Mallory Square.
This pet-friendly apartment in Key West offers a heated swimming pool, a terrace/balcony, and on-site parking, perfect for guests seeking a getaway with a pool.

Located in the Key West Historic District, this historic apartment is just half a block from Duval Street and within walking distance of the Historic Seaport, offering a prime location for exploring the city's attractions.
This apartment features a heated swimming pool, a terrace/balcony, and is pet-friendly, providing a comfortable stay with a capacity for 2 guests.