This Key West seaside property is situated within 3.2km of the Key West Tropical Forest and Botanical Garden, Fort East Martello Museum and Gallery, and the Key West Art and Historical Society. This 65 square metre house boasts one bedroom, one bathroom, sleeps six, and includes a fully equipped kitchen, swimming pool, Jacuzzi, and terrace; enjoy ocean views and on-site barbecue facilities.
Key West, FL
01/10 – 01/11
£379/nighttotal: £11749 (31 )
Sea Breeze Villa
1 2
house , Key West
Sea Breeze Villa is a detached house located in Key West, a 9-minute walk from Higgs Beach and 1 kilometre from the city centre, offering convenient access to the Key West Aquarium and Mallory Dock, which are 2.4 kilometres away. This air-conditioned holiday home spans 126 square metres, accommodates up to 11 guests with three bathrooms, and features a heated swimming pool, spa, tennis court, fully equipped kitchen with a dishwasher and oven, free Wi-Fi, and free private parking.
9.5 117 reviews
Key West, FL
11/07 – 18/07
£1003/nighttotal: £7021 (7 )
Havana Lane: An Updated Classic Conch Cottage With Still A Rustic Edge!
1 4
cottage , Key West
This charming cottage is located in Old Town Key West, just a short walk from the White Street Art District and a 1.1 km walk or cycle ride from Duval Street and the Historic Seaport. The cottage enjoys an excellent user rating, location rating, and cleanliness rating, indicating a high standard of accommodation and service. The cottage spans 95 square metres and comfortably sleeps up to four guests in its two bedrooms and two bathrooms. The property offers a range of amenities and features, including a private courtyard with a swimming pool, a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, a garden, a spa, parking, and a relaxing outdoor living area.
Key West, FL
29/12 – 27/01
£395/nighttotal: £11455 (29 )
The Cozy Starfish By Last Key Realty
1 2
house , Key West
The Cozy Starfish is a holiday home in Key West, located 0.8 kilometres from Southernmost Point and within 500 metres of the city centre, offering an 8-minute walk to Fort Zachary Taylor State Park Beach and a 7-minute walk to Duval Street. This accommodation provides 56 square metres of living space with 2 bedrooms, sleeping up to 7 guests, and features a fully equipped kitchen, private parking, free WiFi, air conditioning, a swimming pool, spa, and tennis court, ideal for exploring Ernest Hemingway Home and Museum and Key West Aquarium.
9.8 75 reviews
Key West, FL
06/01 – 08/01
£947/nighttotal: £1894 (2 )
Alligator Reef Light Suite
2 5
house , Key West
This luxury Key West suite, situated in Old Town, is a half-block from Duval Street and within walking distance (0.8km) of the Ernest Hemingway Home and Museum and 1.9km from Fort Zachary Taylor Historic State Park. The two-bedroom apartment sleeps six, offering a king and queen bed plus a queen sofa bed, a fully equipped kitchen with granite worktops, and access to shared heated plunge pools, a fire pit, outdoor kitchen, and BBQ facilities.
Key West, FL
01/08 – 08/08
£2838/nighttotal: £19866 (7 )
Rigby House - Brand New With Private Pool
6 11
house , Key West
Rigby House, a six-bedroom property in Key West's central district, is within 0.8 km of Mallory Dock, 0.6 km of Simonton Street Beach, and 0.4 km of the Key West Aquarium. This large Key West holiday home boasts 232 square metres of space, sleeps 20 guests, and includes a private swimming pool, fully equipped kitchen, and free Wi-Fi.
Key West, FL
01/10 – 01/11
£174/nighttotal: £5394 (31 )
99 M² House ∙ 2 Bedrooms ∙ 8 Guests
2 2
house , Key West
This classic Key West villa is located in a sought-after district, offering easy access to nearby attractions such as Duval Street, which is approximately 1.2 kilometres away, and the Ernest Hemingway Home and Museum, just 0.8 kilometres distant. This 99 square metre residence accommodates up to eight guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, and a terrace, with a king bed that can be configured as two twins and a trundle bed for flexible sleeping arrangements.
10 6 reviews
Key West, FL
01/10 – 01/11
£187/nighttotal: £5797 (31 )
House ∙ 3 Bedrooms ∙ 8 Guests
3 2
house , Key West
This detached house in Key West is located in a quiet neighbourhood, 5 minutes by bicycle from Higgs and Smathers beaches and 10 minutes by bicycle or Uber from Duval Street. This family-friendly property accommodates up to eight guests and features a private heated and chilled swimming pool with a waterfall, a fully equipped kitchen with quartz countertops and new stainless steel appliances, and off-street parking for up to three vehicles or a boat trailer.
9.6 101 reviews
Key West, FL
05/09 – 19/09
£302/nighttotal: £4228 (14 )
Tranquility By Avantstay Close To Duval St W Bbq Shared Pool
1 4
house , Key West
This charming cottage is ideally located in the heart of Key West's Historic District, just a short walk from Duval Street and the Key West Cemetery, making it perfect for exploring the island's rich history and vibrant culture. The property has received excellent reviews from previous guests, highlighting its convenience, comfort and value for money. The cottage offers a comfortable and spacious layout, with a fully equipped kitchen and modern amenities including air conditioning, a private pool and free Wi-Fi. Guests can enjoy relaxing on the terrace, making use of the barbecue facilities or simply soaking up the sun in the garden.
Key West, FL
27/06 – 04/07
£319/nighttotal: £2233 (7 )
Colony Poolside
1 2
house , Key West
This Key West holiday home is centrally located, just 0.9 km from South Beach and close to Ernest Hemingway's House, Duval Street, and the Southernmost Point. The 51-square-metre property offers one bedroom, one bathroom, sleeps three guests, and features a private garden, swimming pool, spa, tennis court, and a fully equipped kitchen including a fridge and microwave.
10 3 reviews
Key West, FL
01/08 – 08/08
£989/nighttotal: £6923 (7 )
446 M² Villa ∙ 6 Bedrooms ∙ 16 Guests
6 11
house , Key West
This substantial six-bedroom, seven-bathroom residence, a luxurious penthouse and separate three-bedroom guest house, is situated in the heart of Old Town Key West, mere steps from Duval Street's dining and entertainment venues. Spanning 446 square meters, this property offers two private heated swimming pools, a hot tub with a waterfall, expansive porches, and a large deck, accommodating up to 16 guests for an exceptional Key West escape.
9.4 7 reviews
Key West, FL
23/11 – 29/11
£514/nighttotal: £3084 (6 )
Key West's Best
2 6
house , Key West
This Key West holiday home is ideally located near Smathers, Rest, and Higgs Beaches, approximately 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home and Museum, with Key West International Airport just 1.9 km away. The two-bedroom, two-bathroom property sleeps up to 11 guests and boasts a private balcony with ocean views, a swimming pool, Jacuzzi, sauna, fitness centre, tennis court, and well-equipped kitchen; nearby activities include exploring the beaches and visiting local attractions.
Best Key West, FL villas and holiday homes with air conditioning
Key West, FL
11/07 – 18/07
£328/nighttotal: £2296 (7 )
Kwss108 Sunrise Suites - Martinique Suite 108
2 4
house , Key West
KWSS108 Sunrise Suites - Martinique Suite 108 offers a convenient location in Key West, situated 1 kilometre from Key West International Airport and approximately 6.4 kilometres from Southernmost Point and Duval Street. This 72 square metre holiday apartment accommodates up to 11 guests in 2 bedrooms and features 2 bathrooms, a well-equipped kitchen with a dishwasher, microwave oven, and fridge, air conditioning, a swimming pool, jacuzzi, and a private balcony.
10 2 reviews
Key West, FL
06/07 – 09/07
£309/nighttotal: £927 (3 )
Duval Hideaway
2 6
house , Key West
Duval Hideaway is centrally located in Key West, Florida, a short walk (0.6 km) from Duval Street, the Ernest Hemingway Home and Museum, and South Beach. This two-bedroom, one-bathroom property offers 73 square metres of living space, sleeps up to seven guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, air conditioning, and a balcony.
Key West, FL
21/12 – 18/01
£359/nighttotal: £10052 (28 )
Seaport Serenity Cottage - Quiet And Quaint
1 1
house , Key West
Seaport Serenity Cottage, a detached house, is located in Key West, 965 metres from the city centre, a 14-minute walk to Simonton Street Beach and approximately 1.6 kilometres from the Ernest Hemingway Home and Museum. This cottage offers accommodation for up to 11 guests with 2 bathrooms, a floor area of 111 square metres, a fully equipped kitchen including a dishwasher and oven, air conditioning, free WiFi, a terrace with outdoor dining, and private parking.
10 2 reviews
Key West, FL
02/07 – 05/07
£521/nighttotal: £1563 (3 )
Sombrero Reef Light Suite
1 4
house , Key West
Sombrero Reef Light Suite is a centrally located Key West property, a short 0.8km walk from South Beach and the Ernest Hemingway Home and Museum, and less than 1.6km from Duval Street and Mallory Square, placing it within Key West's historic district. This self-catering apartment offers 48 square metres of space, sleeping up to seven guests in one bedroom and one bathroom, and includes a fully equipped kitchen with dishwasher, air conditioning, a swimming pool, and free Wi-Fi.
Our Favourite Holiday Homes with a Hot Tub in Key West, FL
Every holiday home with a jacuzzi in Key West, FL provides a secluded sanctuary for a private hot tub soak each evening.
9.3 3 reviews
Key West, FL
13/09 – 27/09
£323/nighttotal: £4522 (14 )
Conch In The Treetops By Last Key Realty
1 2
house , Key West
Conch in the Treetops is a Key West property situated 1.9 km from Key West International Airport and within a short drive of landmarks such as the Southernmost Point, Ernest Hemingway Home and Museum, Duval Street, and Mallory Square. This 126 square metre house boasts two bedrooms, two bathrooms, sleeps eleven guests, and features a private pool, jacuzzi, spa, fitness centre, tennis court, and free parking, plus a fully equipped kitchen and free Wi-Fi.
9.2 151 reviews
Key West, FL
29/12 – 27/01
£569/nighttotal: £16501 (29 )
Ocean Hideaway On The Atlantic
2 2
house , Key West
Ocean Hideaway on the Atlantic, a Key West apartment, is situated near Smathers Beach, approximately 2.6 km from the Southernmost Point and 3.2 km from the Ernest Hemingway Home. This 126 square metre self-catering flat boasts two bedrooms, two bathrooms, a living room, and a fully equipped kitchen, plus amenities including a swimming pool, jacuzzi, and tennis court; free Wi-Fi and on-site parking are also provided.
Key West, FL
11/07 – 18/07
£758/nighttotal: £5306 (7 )
3 4 Tim E
4 4
house , Key West
This property is situated in Key West, 1.9 kilometres from the airport and within a few kilometres of attractions including the Ernest Hemingway Home and Museum (3.7 km), Key West Aquarium (4.3 km), Mallory Dock (4.3 km), Duval Street (3.9 km), and Southernmost Point. This spacious holiday home accommodates up to 15 guests, offering a private swimming pool and hot tub, free Wi-Fi, free private parking, and a well-equipped kitchen with a dishwasher, oven, and microwave, alongside a balcony with sea views and 4 bathrooms.
Key West, FL
29/12 – 27/01
£376/nighttotal: £10904 (29 )
Kw361flr Egret House
2 2
house , Key West
This Egret House is located just over 4 kilometres from Key West International Airport and approximately 8 kilometres from Duval Street, the Southernmost Point, Key West Aquarium, and Mallory Dock, with the Ernest Hemingway Home and Museum also being 7.7 kilometres away. This 73 square metre dwelling offers accommodation for up to 11 guests, featuring 2 bedrooms, 1 bathroom, air conditioning, a hot tub, a private balcony, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Frequently asked questions about villa rentals in Key West, FL
What are the must-see attractions in Key West, FL?
You can't miss the Southernmost Point of the Continental US, a popular photo op. The Ernest Hemingway Home and Museum is a must-see for literature lovers, and the Key West Aquarium is a great place for families. If you're looking for a bit of history, check out Fort Zachary Taylor Historic State Park.
What indoor activities for families are available in Key West, FL on rainy days?
The Key West Butterfly and Nature Conservatory is a great place to escape the rain and learn about butterflies. The Mel Fisher Maritime Museum is also a good option, with lots of exhibits on shipwrecks and treasure. Of course, there's always the Key West Aquarium, which is a great choice for a rainy day.
What are the best holiday homes with a pool in Key West, FL?
Key West is all about enjoying the outdoors! Take a sunset sail on the Gulf of Mexico, rent a kayak or paddleboard and explore the mangroves, or just relax on the beach. For a bit of history, wander through the Old Town and check out the many historic buildings. And don't forget to try some fresh conch fritters!
What are the best holiday homes with a jacuzzi in Key West, FL?
What are the advantages of renting a house or a villa in Key West, FL
Renting a villa gives you more space and privacy than a hotel, often with a private pool and outdoor living areas. You can also save money on dining by cooking some meals in the kitchen. Many villas are located in quiet neighbourhoods, offering a more peaceful experience than a hotel in the heart of the action.
What are the best holiday homes for families and kids in Key West, FL?
What food festivals or culinary events take place in and around Key West, FL?
The biggest culinary event in Key West is the annual Key West Food & Wine Festival, held in January. The festival features tastings from local restaurants, cooking demonstrations, and wine seminars. There are also several other smaller food events throughout the year, such as the Key West Lobsterfest and the Key West Seafood Festival.
What are the best pet friendly holiday homes in Key West, FL?
What exclusive experiences are available when visiting Key West, FL?
You can take a private fishing charter, go on a sunset cruise with a small group, or even book a private tour of the Hemingway Home and Museum. For a truly unique experience, consider renting a vintage car and exploring the island at your own pace.
What are the best holiday homes with parking in Key West, FL?
Which part of Key West, FL would be ideal for a villa rental?
The Old Town area is great for being close to the action, but if you prefer a quieter stay, consider renting a villa in the New Town area or out on the ocean side of the island. The historic Bahama Village neighbourhood is also a popular choice for villa rentals.
Destinations nearby
Best Key West, FL villas and holiday homes with a kitchen
8.8 93 reviews
Key West, FL
28/06 – 02/07
£322/nighttotal: £1288 (4 )
Dog-friendly Cottage With Private Hot Tub & Garden - Great Downtown Location
2 4
cabin , Key West
This cottage is located in Old Town Key West, just 50 metres from Duval Street, and within walking or cycling distance of the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This 75 square metre property accommodates up to six guests with two bedrooms and one bathroom, featuring a private garden with a hot tub, a kitchen, air conditioning, complimentary WiFi, and private parking.
9.3 3 reviews
Key West, FL
22/08 – 29/08
£328/nighttotal: £2296 (7 )
Petes East Cottage
2 2
house , Key West
Petes East Cottage enjoys a prime Key West location, a short walk (0.6km) from South Beach and close to the Ernest Hemingway Home and Museum and Duval Street. This 65 square metre self-catering property sleeps seven, boasting two bedrooms, one bathroom, a private patio, swimming pool, tennis court, free Wi-Fi, and access to a garden; nearby cycling explores the island's attractions including Fort Zachary Taylor State Park Beach and Higgs Beach.
9.3 19 reviews
Key West, FL
05/09 – 19/09
£337/nighttotal: £4718 (14 )
122 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 4
house , Key West
This Key West property is situated near Smather's Beach, a short walk from a couple of kilometres of Atlantic Oceanfront promenade, and adjacent to nature preserves. This two-bedroom, two-bathroom house offers 122 square metres of living space, including a modern living room, king-size beds in each bedroom, a queen sleeper sofa, Olympic-sized pool, tennis courts, and a covered garage; accommodating up to six guests and providing access to nearby nature trails.
10 1 review
Key West, FL
08/07 – 09/07
£755/nightfor 1 night
Pescado Penthouse
3 2
house , Key West
Pescado Penthouse, a Key West holiday home, is centrally located less than 1.6km from Mallory Dock, Duval Street, and Mallory Square, and a 0.5km stroll from South Beach. This three-bedroom, three-bathroom property sleeps seventeen guests, boasts two living rooms, a fully equipped kitchen, and is conveniently situated 4km from Key West International Airport.
Best Holiday Houses with a Swimming Pool in Key West, FL
On-site pool access at your holiday home in Key West, FL makes a refreshing dip the perfect way to complement a day by the water.
10 2 reviews
Key West, FL
06/01 – 08/01
£2329/nighttotal: £4658 (2 )
The Crestwood House - Private Heated Pool & Parking
6 5
house , Key West
This six-bedroom Key West holiday home is situated approximately 4 kilometres from Key West International Airport and 8 kilometres from downtown attractions including the Ernest Hemingway Home and Mallory Square. Offering 269 square metres of space, this property sleeps 22 guests and boasts a private heated pool, parking, a fully equipped kitchen, fitness centre access, and sea views.
8.5 2 reviews
Key West, FL
29/12 – 31/12
£891/nighttotal: £1782 (2 )
Number Eleven At Scarlet Mango Inn Key West
1 2
house , Key West
NUMBER ELEVEN at Scarlet Mango Inn is located in Key West, a 11-minute walk from Mallory Dock and 0.6 miles (approximately 965 metres) from Mallory Square, with Simonton Street Beach a 10-minute walk away. This air-conditioned one-bedroom cottage accommodates up to three guests and offers on-site parking, free Wi-Fi, and access to an outdoor swimming pool, ideal for exploring Key West's attractions.
8.8 188 reviews
Key West, FL
22/08 – 29/08
£320/nighttotal: £2240 (7 )
Sandpiper On The Ocean
2 2
house , Key West
Sandpiper on the Ocean, a Key West apartment, offers superb beachfront proximity, being a 4-minute walk from Smathers Beach and within 2.6km of the Southernmost Point and Ernest Hemingway Home. This two-bedroom, two-bathroom flat sleeps families or groups, boasting a fully equipped kitchen, private balcony with ocean views, on-site parking, a swimming pool, Jacuzzi, and complimentary Wi-Fi; tour organisation services are also available.
Key West, FL
30/12 – 10/01
£856/nighttotal: £9416 (11 )
Tropical Cottage Tropical Village
4 5
house , Key West
This Key West cottage is centrally located, just 0.4km from South Beach and 0.6km from the Southernmost Point buoy, offering easy access to Duval Street and the Ernest Hemingway Home. The two-bedroom, two-bathroom property sleeps nine guests and boasts a swimming pool, spa, tennis court, and fully equipped kitchen including a dishwasher, plus free Wi-Fi; nearby cycling opportunities explore the island.
Discover Holiday Homes by the Sea in Key West, FL
Base your next maritime trip at comfortable coastal holiday homes located a short distance from beaches in Key West, FL.
9.8 15 reviews
Key West, FL
08/07 – 09/07
£663/nightfor 1 night
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-friendly
2 2
house , Key West
Choose the Right 5-Star Holiday Houses in Key West, FL
Sophistication and a prime location define these luxury holiday homes in Key West, FL, offering premium amenities for a superior stay.
Key West, FL
01/10 – 01/11
£384/nighttotal: £11904 (31 )
Casita Olivietta By Last Key Realty
1 2
house , Key West
Top Family-Friendly Holiday Homes in Key West, FL
Family-friendly holiday homes in Key West, FL provide ample space and easy access to local attractions, ensuring everyone stays comfortable and entertained.
9.5 30 reviews
Key West, FL
02/07 – 05/07
£890/nighttotal: £2670 (3 )
127 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 4
house , Key West
Key West, FL
01/10 – 01/11
£286/nighttotal: £8866 (31 )
157 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 2
house , Key West
9.1 21 reviews
Key West, FL
20/07 – 27/07
£410/nighttotal: £2870 (7 )
113 M² House ∙ 2 Bedrooms ∙ 6 Guests
2 1
house , Key West
8.6 9 reviews
Key West, FL
11/07 – 18/07
£576/nighttotal: £4032 (7 )
Crawl To Duval W/ Hot Tub
2 4
house , Key West
Top-Rated Dog-Friendly Holiday Houses in Key West, FL
Your dog-friendly holiday home in Key West, FL ensures easy beach access and handy outdoor taps for cleaning.
Key West, FL
30/12 – 10/01
£639/nighttotal: £7029 (11 )
The Grand Cayman | Beautifully Remodeled Key West Condo!
2 5
house , Key West
10 1 review
Key West, FL
30/10 – 04/11
£1363/nighttotal: £6815 (5 )
Louisa House
4 2
house , Key West
9.8 81 reviews
Key West, FL
06/01 – 08/01
£1584/nighttotal: £3168 (2 )
Luxury Waterfront Home With Private Pool
4 5
apartment , Key West
Key West, FL
05/09 – 19/09
£928/nighttotal: £12992 (14 )
Queen Of Louisa By Last Key Realty
1 4
house , Key West
Check Out Holiday Homes with Parking in Key West, FL
Having a car park at your holiday home in Key West, FL ensures the coast is easy to reach every day with no extra faff.
9.8 150 reviews
Key West, FL
06/01 – 08/01
£1829/nighttotal: £3658 (2 )
3-story Spacious Conch Style Home W/ Private Pool & Dock!
