Villas and Vaction Homes in Key West, FL

Conveniently located 0.6 miles from Key West International Airport, this Key West condo is approximately 2.8 miles from Safe Harbor, offering easy access to island living and attractions like the Southernmost Point and Ernest Hemingway Home and Museum, both about 4.3 miles away.
This remodeled 800 square foot villa accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a microwave and dishwasher, making it an ideal holiday home for exploring Key West.

Located in Old Town Key West, this historic estate is just 3.5 streets from Duval Street and within walking distance to Mallory Square Sunset Celebration and the Historic Seaport.
This expansive 7-bedroom, 5.5-bathroom villa offers 4530 sq ft of living space, accommodating up to 16 guests with a private pool, wraparound porches, and a separate studio cottage, making it an ideal holiday home.

Located in Key West, this holiday home is a 4-minute walk from Smathers Beach and 1.2 miles from Key West International Airport, offering a private entrance and ocean views from its balcony.
This 1310 square foot villa provides accommodation for up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen, a swimming pool, a sauna, and a garden for outdoor enjoyment.

Located in Upper Bayview North, this villa is a short 19-minute walk to Rest Beach and offers proximity to Duval Street and the Ernest Hemingway Home and Museum.
This expansive holiday home accommodates up to 15 guests with 4 bedrooms and 4 bathrooms, featuring sea views, a well-equipped kitchen with a dishwasher and microwave, air conditioning, a terrace, and on-site parking.

Located just a few blocks from Key West's city center, this welcoming villa is a 5-minute walk to the Key West Aquarium and Simonton Street Beach, and within 1.1 miles of the Ernest Hemingway Home and Museum and Southernmost Point.
This 3-bedroom holiday home offers a private outdoor pool, a balcony with pool views, an outdoor dining area, on-site parking, and complimentary Wi-Fi, making it ideal for extended stays.

Located just 1.2 miles from Key West International Airport and 2.3 miles from the Ernest Hemingway Home and Museum and Duval Street, this vacation home offers sea views for a classic Key West experience.
This exclusive 4-bedroom villa, accommodating up to 15 guests, features a private pool, hot tub, complimentary WiFi, and concierge service, making it an ideal holiday home for exploring Key West.

Located in a secluded compound within Old Town Key West, this one-bedroom apartment offers a peaceful retreat just steps from Duval Street, providing convenient access to shops and dining.
This welcoming villa features a private deck for sunning and al fresco dining, a large shared swimming pool, and a nautical-themed interior, accommodating up to 4 guests with a fully appointed kitchen and air conditioning.

Prime Old Town Key West location, this apartment is situated two blocks east of Duval Street and within walking distance to St. Mary's Star of the Sea Basilica, the Historic Seaport, and Higgs and Smathers Beaches.
This 900 sq ft, 2-bedroom apartment accommodates up to 4 guests and features a modern eat-in kitchen, private outdoor spaces with a grill, off-street parking, and a community swimming pool, offering a perfect holiday home experience.

Runaway Bills offers a prime Key West location, situated just 600 yards from the city center and a 12-minute walk to South Beach, placing you within easy reach of the Ernest Hemingway Home and Museum and Duval Street.
This spacious 850 square foot villa, featuring 3 bedrooms and accommodating up to 11 guests, boasts a private entrance, an outdoor swimming pool, and a fully equipped kitchen, making it an ideal holiday home for exploring Key West.

Offering a prime waterfront location in Key West, this holiday home is situated 1.3 miles from the Southernmost Point and 1.5 miles from the Key West Aquarium, providing convenient access to local attractions.
This welcoming 1190 square foot villa boasts 2 bedrooms and 2 bathrooms, accommodating up to 13 guests with a private dock, outdoor swimming pool, and complimentary WiFi.

Located in Key West's prime Old Town Historic District, this cottage is steps from Duval Street and less than 0.5 miles from Fort Zachary Taylor Historic State Park and its beach.
This 800 sq ft villa offers two separate studio suites, a private patio with a jacuzzi, off-street parking, and in-home guest services for up to 4 guests.

Steps from South Beach, this Key West villa is located half a mile from the city center, offering convenient access to Southernmost Point, Ernest Hemingway Home and Museum, and Duval Street, with Mallory Dock and Square 1.3 miles away.
This welcoming holiday home features air conditioning, a kitchen with a fridge and microwave, and accommodates up to 7 guests within its 400 square feet of floor area.

Located 1.2 miles from Key West International Airport, this welcoming villa is situated 2.4 miles from the Ernest Hemingway Home and Museum and Duval Street, and 2.6 miles from Southernmost Point.
This 4-bedroom, 3-bathroom holiday home comfortably accommodates 15 guests and features an exclusive private swimming pool, hot tub, full kitchen with a dishwasher, free WiFi, and private parking, offering sea views and a private entrance.

Located just 600 feet from Key West's city center and a 3-minute walk to South Beach, this holiday home offers exclusive access to attractions like the Southernmost Point and Ernest Hemingway Home and Museum.
This spacious 1570 sq ft villa features 4 bedrooms, 4 bathrooms, a private swimming pool, and a fully equipped kitchen, accommodating up to 23 guests with complimentary WiFi and parking.

Puerta Coralina is located in Key West, a short walk to the city center and South Beach, with the Key West Aquarium and Mallory Dock 1.2 miles away.
This 1360 square foot villa offers accommodation for 11 guests with a private pool, air conditioning, and a fully equipped kitchen, making it a perfect holiday home.

Located in Old Town Key West, this property is steps from the quieter upper Duval neighborhood and the Southernmost Point, with easy walking distance to lower Duval Street and Fort Zachary Taylor Historic State Park.
This 1450 sq ft villa, a welcoming holiday home split between a main house and a separate cottage, accommodates 8 guests with 4 bedrooms, 4 bathrooms, a private heated pool, and an expansive outdoor living space featuring a covered lounge and gas barbeque.

Located in Key West, this welcoming villa is a 9-minute walk from Smathers Beach and 2 miles from the iconic Southernmost Point.
This 1100 square foot holiday home offers 2 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher and oven, and access to a communal swimming pool and hot tub, all within a secure gated community.

Directly on Key West's Riviera canal, this waterfront holiday home offers a private dock and 50 ft seawall for immediate Gulf and Ocean access, ideal for boaters exploring the waters just miles away.
This expansive 2,300 sq ft villa features 3 bedrooms and 2 bathrooms, comfortably sleeping 12 guests with a dedicated game room including ping-pong and Foosball, alongside a private swimming pool and garden for an exclusive Key West experience.

Atlantic Parrot is a welcoming villa located in Key West, just a 2-minute walk from Smathers Beach and 1.7 miles from Southernmost Point, offering convenient access to Ernest Hemingway Home and Museum and Duval Street, 2.1 miles away.
This 1310 square foot holiday home accommodates up to 9 guests with 2 bedrooms, features a fully equipped kitchen with a dishwasher and oven, air conditioning, internet, and an outdoor swimming pool, all accessible via an elevator and located 1.2 miles from Key West International Airport.

Experience a prime Old Town Key West location, just a half-block from the quieter end of Duval Street and three blocks from the beach at Duval & South Streets, offering convenient walking access to numerous restaurants, art galleries, and shopping.
This welcoming 1020 sq ft villa is a Key West style cottage featuring a private small pool, a covered front porch, two bedrooms with king beds and adjoining baths, a fully equipped kitchen, and high-speed wireless internet, accommodating up to 4 guests with available parking.