This Key West property, situated in Osprey Colony, offers convenient access to Duval Street, South Beach, and the city centre, lying within a short walk of these key areas and less than 3km from Key West International Airport. The 45 square metre house features one bedroom, one bathroom, sleeps seven guests and includes a private balcony, swimming pool, tennis court, free Wi-Fi, and a fully equipped kitchen; cycling opportunities abound in the surrounding area.
Key West, FL
29/12 – 27/01
1307 ﺩ.ﺇ/nighttotal: 37903 ﺩ.ﺇ (29 )
Blue Horizon Hideaway
3 2
house , Key West
This Key Cove townhouse provides waterfront accommodation on two sides, situated a mere 5 minutes' drive from Key West's shopping, dining, and Duval Street. This family-friendly property accommodates up to six guests with two bedrooms and two bathrooms, featuring a private outdoor patio, a shared community swimming pool, and a chef's kitchen with a wet bar.
9.5 2 reviews
Key West, FL
11/11 – 14/11
3773 ﺩ.ﺇ/nighttotal: 11319 ﺩ.ﺇ (3 )
Blue Haven Unit B416
2 4
house , Key West
Blue Haven Unit B416, a Key West holiday home, is conveniently located a short walk from Smathers Beach and within 3.2km of the Southernmost Point and Ernest Hemingway Home and Museum. This 139 square metre property boasts two bedrooms, two bathrooms (including a hot tub), a fully equipped kitchen, and can accommodate up to 11 guests, offering a swimming pool, Jacuzzi, tennis court, and fitness centre.
Key West, FL
29/12 – 27/01
2259 ﺩ.ﺇ/nighttotal: 65511 ﺩ.ﺇ (29 )
Shady Nook
2 2
house , Key West
This holiday cottage, SHADY NOOK, is situated in central Key West, 400 metres from Duval Street and a 14-minute walk to Fort Zachary Taylor State Park Beach. This air-conditioned property accommodates up to seven guests, offering two bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, complimentary WiFi, private parking, and an on-site swimming pool.
9.0 2 reviews
Key West, FL
08/07 – 09/07
2225 ﺩ.ﺇ/nightfor 1 night
Kingfish Keep
1 2
house , Key West
Kingfish Keep, a centrally located Key West property, is a short walk from South Beach, the Southernmost Point buoy, and Duval Street. This one-bedroom, one-bathroom house sleeps seven, boasts a fully equipped kitchen with fridge and microwave, free Wi-Fi, air conditioning, and is within easy reach of Fort Zachary Taylor State Park Beach.
9.6 108 reviews
Key West, FL
06/01 – 08/01
6362 ﺩ.ﺇ/nighttotal: 12724 ﺩ.ﺇ (2 )
Keys Please!
3 5
house , Key West
Keys Please! is centrally located in Key West, Florida, a 0.7km walk from the Ernest Hemingway Home and Museum, 0.8km from Duval Street, and a 0.5km walk from South Beach. This 114 square metre, three-bedroom house boasts a private pool, garden, and parking, plus a fully equipped kitchen including a dishwasher and microwave, and offers free Wi-Fi; ideal for families or groups.
9.9 27 reviews
Key West, FL
06/01 – 08/01
4025 ﺩ.ﺇ/nighttotal: 8050 ﺩ.ﺇ (2 )
Coral Oasis: 3br Retreat, Pool, Dogs Ok, Parking
3 5
house , Stock Island
This Stock Island townhouse, part of the Coral Oasis gated community, is situated just over the Cow Key Bridge from Key West, 0.5km from Fort Zachary Taylor State Park Beach and 4.2km from Smathers Beach. The three-bedroom, three-bathroom property sleeps six guests, offering a fully equipped kitchen, a shared heated swimming pool, and two off-street parking spaces; pets under 25 lbs are welcome (fees apply).
9.7 172 reviews
Key West, FL
06/01 – 08/01
8394 ﺩ.ﺇ/nighttotal: 16788 ﺩ.ﺇ (2 )
Waterlane House -Pool & Boat Dock
4 5
house , Key West
This four-bedroom apartment is situated in Sugarloaf Shores, a peaceful area 19 kilometres from Key West's city centre, offering a tranquil escape from the bustling tourist hub. This accommodation has received excellent ratings for its cleanliness, location, and overall experience. The apartment comes with a fully equipped kitchen, including a fridge, microwave, and dishwasher. Guests can enjoy amenities such as a swimming pool, a fitness centre, and a restaurant on-site, as well as a terrace or balcony, a garden, and parking.
9.7 6 reviews
Key West, FL
05/09 – 19/09
2053 ﺩ.ﺇ/nighttotal: 28742 ﺩ.ﺇ (14 )
Tropical 2br | Pool | Deck | W/d
2 4
house , Key West
This detached property is situated in a small, gated community within Old Town Key West, offering convenient access on foot to notable landmarks such as the Southernmost Point, the Lighthouse, and the Ernest Hemingway Home and Museum, with Duval Street's amenities also a short walk away. This accommodation for four guests boasts two bedrooms and two bathrooms, features air conditioning and internet, and provides a private deck with a gas grill and access to a heated communal swimming pool, alongside a well-equipped kitchen and a Smart TV.
9.0 1 review
Key West, FL
29/12 – 31/12
2358 ﺩ.ﺇ/nighttotal: 4716 ﺩ.ﺇ (2 )
The Gato Room At Inn On Fleming Key West!
1 2
house , Key West
THE GATO ROOM at the Inn on Fleming Key West is centrally located, less than 1.6km from Mallory Square and Duval Street, and a short walk from Simonton Street Beach and the Ernest Hemingway Home and Museum. This one-bedroom, one-bathroom apartment offers 15 square metres of accommodation for two guests, including a swimming pool, tennis court, free Wi-Fi, and on-site parking.
Key West, FL
29/12 – 27/01
1590 ﺩ.ﺇ/nighttotal: 46110 ﺩ.ﺇ (29 )
11 Cottage Close To Duval St
1 2
house , Key West
This Key West cottage is centrally located in the city's downtown district, a short walk (0.8km) from Duval Street and Fort Zachary Taylor State Park Beach. The 39 square metre property offers one bedroom, two living rooms, a fully equipped kitchen (including fridge, microwave, and dishwasher), and sleeps up to seven guests, with free Wi-Fi and private parking included.
Key West, FL
01/08 – 08/08
4675 ﺩ.ﺇ/nighttotal: 32725 ﺩ.ﺇ (7 )
Kw31 Three Flowers Guesthouse
4 11
house , Key West
This Key West holiday home is located a short walk from the aquarium and Mallory Dock, with Duval Street and the Ernest Hemingway Home and Museum nearby, placing you within 1.1 kilometres of Mallory Square and 1.4 kilometres of the Southernmost Point. This 190 square metre villa offers air conditioning, a balcony, and accommodates up to 27 guests across its four bedrooms and four bathrooms, with internet access provided.
Best Key West, FL villas and beach houses with a pool
Among the 1179 accommodations in Key West, FL, here are the 4 best villas and beach houses with a pool
Key West, FL
06/01 – 08/01
3673 ﺩ.ﺇ/nighttotal: 7346 ﺩ.ﺇ (2 )
Magical Ocean Penthouse
2 5
house , Key West
This Key West penthouse apartment is ideally located near Smathers Beach, 2.6 km from the Southernmost Point, and 3.2 km from the Ernest Hemingway Home and Museum. The 126 square metre property boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a well-equipped kitchen, jacuzzi, sauna, spa, fitness centre, tennis court, private parking, and complimentary Wi-Fi.
Key West, FL
27/06 – 04/07
1533 ﺩ.ﺇ/nighttotal: 10731 ﺩ.ﺇ (7 )
Colony Calypso
1 3
house , Key West
Colony Calypso, a holiday home, is located in Key West, 400 metres from the city centre and an 11-minute walk from South Beach, offering proximity to the Ernest Hemingway Home and Museum and Duval Street. This property boasts a 49 square metre floor area, accommodating up to 7 guests with 1 bedroom and 1 bathroom, and features a fully equipped kitchen, air conditioning, a swimming pool, spa, fitness centre, tennis court, and private patio with an outdoor dining area.
10 1 review
Key West, FL
04/09 – 07/09
1213 ﺩ.ﺇ/nighttotal: 3639 ﺩ.ﺇ (3 )
Cohiba At Azul Mansion Key West
1 2
house , Key West
COHIBA at Azul Mansion, a Key West apartment, is situated close to South Beach (a 12-minute walk) and within 1.9km of the Key West Aquarium and Mallory Dock. This one-bedroom, one-bathroom property sleeps two, offering free WiFi, on-site parking, a swimming pool, and a terrace; nearby attractions include the Ernest Hemingway Home and Museum and Duval Street.
Key West, FL
20/07 – 27/07
1361 ﺩ.ﺇ/nighttotal: 9527 ﺩ.ﺇ (7 )
Colony Poolside
1 1
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.
Best Key West, FL houses with a kitchen
9.0 2 reviews
Key West, FL
11/07 – 18/07
1742 ﺩ.ﺇ/nighttotal: 12194 ﺩ.ﺇ (7 )
The Mellow Macaw By Last Key Realty
2 4
house , Key West
The Mellow Macaw property is centrally located in Key West, Florida, less than 1.6km from Higgs Beach and a 6-minute walk to Fort Zachary Taylor State Park Beach, also within a short walk of South Beach and the Ernest Hemingway Home and Museum. This 68 square metre Key West holiday home boasts two bedrooms, one bathroom, and sleeps up to 11 guests, offering a private swimming pool, spa, tennis court, free parking, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
8.7 3 reviews
Key West, FL
11/07 – 18/07
1877 ﺩ.ﺇ/nighttotal: 13139 ﺩ.ﺇ (7 )
Oceanfront Oasis
2 4
house , Key West
This Key West oceanfront property, situated in the La Brisa neighbourhood, is a short 1.9 km from the Southernmost Point and 2.3 km from the Ernest Hemingway Home. This 111 square metre house boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a private balcony, swimming pool, sauna, fitness centre, and tennis court; nearby Smathers Beach is an eight-minute walk away.
8.0 1 review
Key West, FL
11/11 – 13/11
1807 ﺩ.ﺇ/nighttotal: 3614 ﺩ.ﺇ (2 )
Carey's Corner
1 2
house , Key West
This Key West house, situated in Carey's Corner, is a seven-minute walk from the Southernmost Point buoy, half a kilometre from Duval Street, and a three-minute walk from Fort Zachary Taylor State Park Beach. The one-bedroom, one-bathroom property sleeps three, boasts a kitchenette with fridge and microwave, a swimming pool, terrace, free Wi-Fi, and air conditioning; nearby attractions include South Beach and Higgs Beach, with Key West International Airport 4 kilometres away.
Key West, FL
17/07 – 21/07
1577 ﺩ.ﺇ/nighttotal: 6308 ﺩ.ﺇ (4 )
The Caroline Suite
1 4
house , Key West
The Caroline Suite, a Key West apartment, is conveniently located 1.8km from Higgs Beach, 1.9km from the Southernmost Point buoy, and 1.9km from Key West International Airport. This one-bedroom, one-bathroom property offers 33 square metres of living space, sleeping up to seven guests and including a fully equipped kitchen, in-unit laundry, air conditioning, a swimming pool, and free Wi-Fi.
Frequently Asked Questions about villa rentals in Key West, FL
What are the must-see attractions in Key West, FL?
Well, you can't miss the Southernmost Point Buoy, it's the southernmost point in the continental US. Then there's the Ernest Hemingway Home and Museum, where you can see his six-toed cats. And don't forget Mallory Square, where you can watch the sunset with street performers and the famous sunset celebration.
What indoor activities for families are available in Key West, FL on rainy days?
If the weather's not cooperating, take the kids to the Key West Aquarium, where they can see local marine life, or the Butterfly Conservatory, a beautiful indoor garden with hundreds of butterflies. The Mel Fisher Maritime Museum is also a great option, showcasing the history of shipwrecks and treasure.
What are the best villa rentals with a pool in Key West, FL?
Key West is all about the water! Go snorkeling or diving at the Key West National Wildlife Refuge, or take a sunset sail on the Gulf of Mexico. For a more relaxed experience, rent a kayak and explore the mangrove forests around the island.
What are the best villa rentals 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, and you can often find kitchens and laundry facilities. Many villas have private pools and gardens, perfect for relaxing and enjoying the Key West sunshine. You'll also have more flexibility to come and go as you please.
What are the best villa rentals for families and kids in Key West, FL?
What food festivals or culinary events take place in and around Key West, FL?
Key West hosts a number of food events throughout the year, including the Key West Food & Wine Festival in November. This festival features tastings from local restaurants, cooking demonstrations, and wine pairings. The annual Key West Lobsterfest in July is another popular event, celebrating the local lobster catch.
What are the best pet friendly villa rentals in Key West, FL?
What exclusive experiences are available when visiting Key West, FL?
For a truly unique experience, book a private sunset cruise or a private fishing charter. You can also arrange a private tour of the Hemingway Home and Museum, or even a private cooking class with a local chef. If you're feeling adventurous, take a helicopter tour over the Florida Keys for breathtaking views.
What are the best villa rentals with parking in Key West, FL?
Which part of Key West, FL would be ideal for a villa rental?
The Old Town area is a popular choice for villa rentals, as it's close to the main attractions and restaurants. The historic district of Old Town is a charming area with a mix of Victorian and Key West architecture. You'll find a good selection of villas in this area, offering a range of sizes and amenities.
Destinations nearby
Best Key West, FL houses with air conditioning
Key West, FL
14/10 – 16/10
1539 ﺩ.ﺇ/nighttotal: 3078 ﺩ.ﺇ (2 )
Kw33a Leeward Isle
2 2
house , Key West
This Key West holiday home is located a 9-minute walk from South Beach, with the Key West Aquarium and Mallory Square a 16 and 17-minute walk away respectively, and close to Duval Street and the Ernest Hemingway Home and Museum. This 75 square meter property accommodates up to 11 guests with 2 bedrooms and 1 bathroom, featuring air conditioning, a hot tub, and a kitchen equipped with a fridge and microwave.
9.0 3 reviews
Key West, FL
05/09 – 19/09
1293 ﺩ.ﺇ/nighttotal: 18102 ﺩ.ﺇ (14 )
The Geiger Suite At Inn On Fleming Key West!
2 4
house , Key West
THE GEIGER SUITE at the Inn on Fleming Key West offers a central location, a short walk from Simonton Street Beach and the Ernest Hemingway Home and Museum, and under 3.2km from Key West International Airport. This self-catering property boasts a 32 square metre floor area, comprising two bedrooms, one bathroom, and accommodating up to four guests, with amenities including a swimming pool, tennis court, free parking, and Wi-Fi.
9.8 81 reviews
Key West, FL
06/01 – 08/01
7797 ﺩ.ﺇ/nighttotal: 15594 ﺩ.ﺇ (2 )
Luxury Waterfront Home With Private Pool
4 5
apartment , Key West
This Key West holiday home, situated in the Northside Resort, is less than 5km from Duval Street, Mallory Square, and the Unitarian Universalist Fellowship of Key West, offering easy access to the island's main attractions. The four-bedroom property sleeps eight guests and boasts a private pool, Jacuzzi, fully equipped kitchen, free Wi-Fi, and concierge services; on-site housekeeping is available on request.
9.6 95 reviews
Key West, FL
06/01 – 08/01
7797 ﺩ.ﺇ/nighttotal: 15594 ﺩ.ﺇ (2 )
Spacious Waterfront 4 Bedroom Home
4 5
apartment , Key West
This four-bedroom house is located in Northside Resort, just three miles from Duval Street, Mallory Square, and The Unitarian Universalist Fellowship of Key West. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The 368 square metre house can accommodate up to eight guests, offering plenty of space for families or groups of friends. Amenities include a private pool, Jacuzzi, terrace, garden, and concierge services, along with a fully equipped kitchen, free Wi-Fi, and parking.
Best Key West, FL villas and beach houses with jacuzzi
Key West, FL
17/07 – 21/07
11866 ﺩ.ﺇ/nighttotal: 47464 ﺩ.ﺇ (4 )
The Duke And The Duchess By Last Key Realty
1 4
house , Key West
This Key West holiday home is centrally located, a 1.1 km walk from Fort Zachary Taylor State Park Beach and 0.6 km from South Beach, offering easy access to the city centre and other attractions. This eight-bedroom, eight-bathroom property boasts 343 square metres of living space, accommodating up to 43 guests and featuring a private pool, jacuzzi, spa, and tennis court, alongside a fully equipped kitchen and free Wi-Fi and parking.
9.3 239 reviews
Key West, FL
30/10 – 04/11
2451 ﺩ.ﺇ/nighttotal: 12255 ﺩ.ﺇ (5 )
Latitude Penthouse Key West
2 2
house , Key West
This apartment is located in Key West, just a short walk from Smathers Beach, Rest Beach, and Higgs Beach, offering easy access to the area's beautiful beaches. It has received excellent ratings for location, cleanliness, and user experience. The two-bedroom, two-bathroom apartment spans 143 square meters and comfortably accommodates up to six guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private balcony with sea views, a swimming pool, a jacuzzi, a fitness centre, and a tennis court.
9.0 349 reviews
Key West, FL
26/10 – 28/10
2478 ﺩ.ﺇ/nighttotal: 4956 ﺩ.ﺇ (2 )
Amelia House
3 4
house , Key West
Amelia House, in a prime Key West location, is within walking distance of Duval Street, South Beach, and the Ernest Hemingway Home and Museum. This three-bedroom Key West property, boasting 78 square metres of floor space, offers a private patio, swimming pool, jacuzzi, and spa, alongside free Wi-Fi and a fully equipped kitchenette; sleeping up to six guests.
Key West, FL
17/07 – 21/07
5837 ﺩ.ﺇ/nighttotal: 23348 ﺩ.ﺇ (4 )
Banana Breeze
4 4
house , Key West
This Key West holiday home is situated 3.9 kilometres from the Ernest Hemingway Home and Museum, placing it conveniently close to attractions such as Mallory Dock and the Key West Aquarium, both 4.5 kilometres away, and within 4 kilometres of Duval Street and the Southernmost Point. Accommodating up to 15 guests, this detached property offers a private swimming pool, hot tub, and a balcony with sea views, alongside a well-equipped kitchen featuring a dishwasher, oven, and microwave, with free WiFi and private parking also provided.
