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1179 Villa rentals in Key West, FL
Key West, FL
06/20 – 06/21
$403/nightfor 1 night
Chagall's Corner
1 2
house , Key West
This Key West vacation rental is centrally located in Chagall's Corner, a short walk from the Southernmost Point, Fort Zachary Taylor State Park Beach, and Duval Street. The one-bedroom, one-bathroom house sleeps three guests and features a kitchenette, air conditioning, free Wi-Fi, a swimming pool, a fitness center, and a tennis court, with easy access to nearby beaches and attractions like the Ernest Hemingway Home and Museum.
Key West, FL
06/20 – 06/21
$525/nightfor 1 night
Scarlet At Scarlet Mango Inn Key West
1 2
house , Key West
This vacation home is located in Key West, 400 yards from the city center, a 10-minute walk to Simonton Street Beach, and an 11-minute walk from Mallory Dock. This air-conditioned accommodation offers 1 bedroom, 1 bathroom, a balcony, and an outdoor swimming pool, accommodating up to 3 guests with WiFi and on-site tennis.
9.4 11 reviews
Key West, FL
06/27 – 06/28
$1061/nightfor 1 night
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock
2 7
house , Key West
This Key West waterfront condo is located approximately 1.1 miles from the Ernest Hemingway Home and Museum and Duval Street, and 1.2 miles from Key West International Airport, offering convenient access to major attractions. This 1300-square-foot property features two bedrooms, two bathrooms, a fully equipped kitchen, a private pool, and free Wi-Fi; it comfortably sleeps 11 guests and is near cycling opportunities.
9.7 3 reviews
Key West, FL
12/30 – 01/10
$863/nighttotal: $9493 (11 )
Duval Street Retreat
2 5
house , Key West
This Duval Street Retreat is centrally located in Key West, Florida, a short walk from the Ernest Hemingway Home and Museum, Duval Street, and South Beach. This 780-square-foot house features two bedrooms, one bathroom, and can comfortably accommodate up to 11 guests, offering free Wi-Fi, private parking, and a balcony; nearby attractions include Fort Zachary Taylor State Park Beach and Higgs Beach.
9.3 3 reviews
Key West, FL
06/20 – 06/21
$1611/nightfor 1 night
St John - Downtown Waterfront Penthouse Pool Parking Dock
4 2
house , Key West
This Key West penthouse, located 1.1 miles from the Ernest Hemingway Home and Museum and Duval Street, offers stunning waterfront views and a private dock. The 2,000-square-foot dwelling boasts four bedrooms, four bathrooms, and accommodates up to 24 guests, featuring a swimming pool, free parking, and free Wi-Fi.
Key West, FL
06/20 – 06/27
$520/nighttotal: $3640 (7 )
Kwss303 Sunrise Suites - Saint Barts Suite 303
2 2
house , Key West
This Key West house is located 0.6 miles from Key West International Airport and within 4 to 4.7 miles of Southernmost Point, the Ernest Hemingway Home and Museum, and Duval Street. This 780 sq ft vacation home offers 2 bedrooms, 2 bathrooms, a capacity for 11 guests, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a Jacuzzi, a terrace, a fitness center, and a tennis court.
10 1 review
Key West, FL
08/22 – 08/29
$326/nighttotal: $2282 (7 )
Cohiba At Azul Mansion Key West
1 2
house , Key West
COHIBA at Azul Mansion, a Key West vacation home, is conveniently located 0.4 miles from Duval Street and a 12-minute walk from South Beach, near attractions like the Key West Aquarium and Mallory Square. This one-bedroom, one-bathroom rental offers air conditioning, a private pool, free Wi-Fi, on-site parking, and accommodates two guests, providing easy access to the Ernest Hemingway Home and Museum and the Southernmost Point.
9.2 55 reviews
Key West, FL
12/30 – 01/10
$822/nighttotal: $9042 (11 )
La Brisa Unit 105 North Building
2 5
house , Key West
La Brisa Unit 105, a Key West vacation rental, offers prime access to beaches like Smathers Beach and attractions such as the Southernmost Point (2 miles away) and Hemingway Home (2.3 miles away), with Key West International Airport just 1.2 miles from the property. This 850-square-foot condo sleeps eight guests in two bedrooms and features a fully equipped kitchen, private patio, swimming pool, Jacuzzi, and on-site parking; in-unit laundry and free Wi-Fi are also included.
Key West, FL
10/26 – 10/28
$527/nighttotal: $1054 (2 )
Kwss202 Sunrise Suites - Big Kahuna Suite 202
2 4
house , Key West
The KWSS202 Sunrise Suites - Big Kahuna Suite 202 is located in Key West, 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point and Duval Street. This 780 square foot suite accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a private balcony, a full kitchen with a dishwasher and microwave, air conditioning, a swimming pool, and a hot tub.
Key West, FL
09/02 – 09/05
$275/nighttotal: $825 (3 )
The Whitehead Room At Inn On Fleming Key West!
1 2
house , Key West
THE WHITEHEAD ROOM at the Inn on Fleming Key West is centrally located, 0.6 miles from Key West's city center, a short walk from Simonton Street Beach, and a mile from Mallory Square, offering easy access to the Ernest Hemingway Home and Museum and Key West International Airport. This 160-square-foot, one-bedroom, one-bathroom Key West vacation rental sleeps two and includes free Wi-Fi, air conditioning, a swimming pool, and on-site parking.
Key West, FL
10/14 – 10/16
$441/nighttotal: $882 (2 )
Andy's Attic
1 2
house , Key West
Andy's Attic, a Key West rental house, is centrally located, a 7-minute walk from the Southernmost Point buoy and a 3-minute walk from Fort Zachary Taylor Historic State Park Beach. This one-bedroom, one-bathroom apartment sleeps three guests and features a private balcony, free Wi-Fi, air conditioning, a kitchenette with a microwave and refrigerator, and a swimming pool.
Key West, FL
12/21 – 01/18
$763/nighttotal: $21364 (28 )
Newly-built, Dog-friendly Home With Shared Pool - Walk To Beach & Dining
3 1
house , Key West
This newly-built house offers a prime Key West location, just a 6-minute walk to South Beach and within 500 feet of the city center, placing you one mile from the Key West Aquarium and a 19-minute walk from Mallory Dock. This dog-friendly vacation rental features 1400 square feet with 3 bedrooms and 3 bathrooms to accommodate up to 11 guests, complete with a full kitchen, air conditioning, a balcony, and access to a shared pool.
Search Vacation Homes with a Pool in Key West, FL
These Key West, FL vacation homes include a swimming pool, so a refreshing dip is always an option during your stay.
9.5 2 reviews
Key West, FL
12/30 – 01/10
$1250/nighttotal: $13750 (11 )
Sundial On The Atlantic Ocean View
2 5
house , Key West
Sundial on the Atlantic Ocean View, a Key West vacation home near Smathers Beach, offers stunning Atlantic Ocean views and is 1.6 miles from the Southernmost Point and 2 miles from the Ernest Hemingway Home and Museum. This 1,350-square-foot property boasts two bedrooms, two bathrooms, a private pool, jacuzzi, and sleeps up to 11 guests, featuring a fully equipped kitchen, fitness center, tennis court, and sauna.
Key West, FL
07/24 – 07/28
$2192/nighttotal: $8768 (4 )
Endless Summer By Last Key Realty
5 7
house , Key West
Endless Summer, a five-bedroom, five-bathroom Key West house rental, is centrally located, a short walk from the Ernest Hemingway Home and Museum and South Beach, and less than a mile from the Southernmost Point. This 1,570-square-foot property boasts a private pool, spa, and tennis court, comfortably accommodating up to 23 guests with amenities including free Wi-Fi, free parking, and a fully equipped kitchen; nearby attractions include Fort Zachary Taylor State Park Beach and Simonton Street Beach.
Key West, FL
08/22 – 08/29
$287/nighttotal: $2009 (7 )
Claro At Azul Mansion Key West
1 2
house , Key West
CLARO at Azul Mansion, a one-bedroom Key West vacation home, is centrally located less than half a mile from the city center and a 12-minute walk from South Beach, placing you within 1.2 miles of the Ernest Hemingway Home and Museum, Duval Street, and Mallory Square. This air-conditioned rental offers a swimming pool, free Wi-Fi, on-site parking, and accommodates two guests, providing easy access to Key West International Airport (1.9 miles away) and nearby attractions.
Key West, FL
10/26 – 10/28
$576/nighttotal: $1152 (2 )
Kwss110 Sunrise Suites - Dominican Suite 110
2 4
house , Key West
This Dominican Suite 110 in Key West is located 0.6 miles from Key West International Airport and approximately 4 miles from Southernmost Point, Ernest Hemingway Home and Museum, and Duval Street. This 800-square-foot condo accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, private balcony, and elevator access.
Best Key West, FL houses with a kitchen
10 4 reviews
Key West, FL
07/02 – 07/03
$882/nightfor 1 night
Sea Esta Suite | Located On Iconic Duval W/ Pool
2 5
house , Key West
This two-bedroom, two-bathroom condo is located in the Duval Square complex, offering direct access to Duval Street and situated just 0.1 miles from the Southernmost Point in Key West. This unit accommodates up to six guests and features a private garage, a rooftop pool, a fully equipped kitchen, and in-unit laundry, with world-class dining and shopping within walking distance.
Key West, FL
09/02 – 09/05
$293/nighttotal: $879 (3 )
Seagull Suite - Southernmost Sanctuary
1 2
house , Key West
The Seagull Suite, a Key West rental house in the South Beach area, is located a short walk from South Beach, 0.6 miles from Duval Street, and a 10-minute walk from the Ernest Hemingway Home. This one-bedroom, one-bathroom apartment sleeps seven guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and a private balcony; nearby attractions include Higgs Beach and Rest Beach, and Key West International Airport is 1.9 miles away.
8.9 12 reviews
Key West, FL
07/02 – 07/03
$2262/nightfor 1 night
St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock
4 5
house , Key West
This Key West waterfront penthouse, a mile from the Ernest Hemingway Home and Museum and Duval Street, offers stunning sea views and private boat dock access. This 2000-square-foot residence boasts four bedrooms, four bathrooms, sleeps sixteen guests, includes a private pool, free Wi-Fi, and elevator access.
8.4 7 reviews
Key West, FL
12/21 – 01/18
$515/nighttotal: $14420 (28 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 1
cottage , Key West
This pet-friendly Key West cottage, located in Old Town, is a short walk from Saint Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to beaches and attractions like the Ernest Hemingway Home and Museum. The one-bathroom rental boasts a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a private porch, and access to a shared pool; it comfortably sleeps two guests and includes on-site barbecue facilities.
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 Buoy, the iconic landmark marking the southernmost point of the continental US. The Ernest Hemingway Home and Museum is a must-visit for literature lovers, and you can't leave Key West without seeing the sunset at Mallory Square.
What indoor activities for families are available in Key West, FL on rainy days?
The Key West Aquarium is a great option for families, with exhibits showcasing local marine life. The Butterfly Conservatory at the Key West Botanical Garden is a beautiful and interactive experience, and the Mel Fisher Maritime Museum offers a fascinating glimpse into the history of shipwrecks.
What are the best villa rentals with a pool in Key West, FL?
Key West is all about enjoying the water, so you can't go wrong with snorkeling, diving, or taking a sunset cruise. If you're looking for something more adventurous, try parasailing or jet skiing. And don't forget to relax on the beach and soak up the sun.
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 house or villa in Key West gives you more space and privacy than a hotel. You'll also have access to a kitchen, laundry facilities, and often a private pool, which can be a big plus, especially for families or groups.
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 is known for its vibrant food scene, and there are several festivals and events throughout the year. The Key West Food & Wine Festival is a highlight, featuring tastings, cooking demonstrations, and more. You can also check out the Key West Lobsterfest and the Key West Seafood Festival.
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, take a sunset sail on a historic schooner or enjoy a private dinner on the beach. You can also book a private fishing charter or go on a guided kayak tour through the mangroves.
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 popular for its historic charm and proximity to attractions. If you prefer a quieter location, consider renting a villa in the New Town area or on the waterfront.
Destinations nearby
Best Key West, FL houses with air conditioning
Key West, FL
07/24 – 07/25
$577/nightfor 1 night
Coconut Palm Suite At Travelers Palm Inn Key West
1 4
house , Key West
The Coconut Palm Suite is conveniently located in Key West, Florida, an 8-minute walk from South Beach and 1.2 miles from the Key West Aquarium and Mallory Square. This one-bedroom Key West rental boasts a fully equipped kitchen with a dishwasher and microwave, a private pool, and accommodates up to 7 guests, perfect for exploring nearby attractions like the Ernest Hemingway Home and Museum and Duval Street.
10 3 reviews
Key West, FL
08/22 – 08/29
$264/nighttotal: $1848 (7 )
Aria At Azul Mansion Key West
1 2
house , Key West
This Key West condo is situated 0.4 miles from the city center, offering a 11-minute walk to the Ernest Hemingway Home and Museum and a 0.6-mile walk to Duval Street. This non-smoking, 1-bedroom, 1-bathroom unit accommodates up to 3 guests and includes air conditioning, a living room, complimentary Wi-Fi, and on-site parking, with access to an outdoor swimming pool and massage services.
Key West, FL
10/14 – 10/16
$419/nighttotal: $838 (2 )
Kw33a Leeward Isle
2 2
house , Key West
This vacation rental is located 200 yards from the city center, a 4-minute walk to Duval Street and a 9-minute walk to South Beach. This 810 sq ft house offers 2 bedrooms, 1 bathroom, and accommodates up to 11 guests with air conditioning, a kitchen, and a hot tub, with pets welcomed.
9.0 1 review
Key West, FL
09/13 – 09/27
$185/nighttotal: $2590 (14 )
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 a mile from Mallory Square and a short walk from the Ernest Hemingway Home and Museum and Simonton Street Beach. This 160-square-foot Key West vacation rental boasts a one-bedroom, one-bathroom layout, accommodating two guests and offering amenities such as a swimming pool, free Wi-Fi, and on-site parking.
Neighborhoods and points of interest in Key West, FL
Best Key West, FL villas and beach houses with jacuzzi
10 7 reviews
Key West, FL
06/20 – 06/27
$1060/nighttotal: $7420 (7 )
3 Bedroom Duval Street Penthouse
3 7
house , Key West
This luxury penthouse offers direct access to Duval Street in Old Town Key West, placing you steps from numerous restaurants, shops, and theaters. This 2200 sq ft residence sleeps 8, featuring 3 bedrooms with private porches, a private backyard oasis with a pool and waterfall, and an exclusive rooftop sun deck with panoramic views.
9.6 198 reviews
Key West, FL
08/22 – 08/29
$390/nighttotal: $2730 (7 )
Poolside Breeze Retreat
2 2
house , Key West
This Key West apartment is just a short walk from Smathers Beach and other popular spots like Rest Beach, Higgs Beach, and the Southernmost Point, offering easy access to the island's best attractions. The apartment boasts consistently excellent ratings for user experience, location, and cleanliness. The apartment has 2 bedrooms, 2 bathrooms, and can comfortably accommodate up to 6 guests in its 1360 square feet of space. You'll enjoy a fully equipped kitchen, a private balcony with ocean views, a swimming pool, a hot tub, a fitness center, and more.
Key West, FL
10/14 – 10/16
$387/nighttotal: $774 (2 )
Kwss108 Sunrise Suites - Martinique Suite 108
2 2
house , Key West
This Key West rental house is located 0.6 miles from Key West International Airport, 4 miles from Southernmost Point, and 4.3 miles from Ernest Hemingway Home and Museum and Duval Street. This 780 square foot house accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, hot tub, balcony, and elevator access.
9.0 206 reviews
Key West, FL
09/13 – 09/27
$363/nighttotal: $5082 (14 )
High Tide In Key West
2 2
house , Key West
This Key West apartment is just a short walk from Smathers Beach, one of the island's most popular beaches, and within a mile of Rest Beach and Higgs Beach. The apartment has received excellent ratings for cleanliness, location, and overall user experience. This two-bedroom rental comfortably accommodates up to six guests. Enjoy modern amenities like air conditioning, free Wi-Fi, a private balcony with ocean views, and a fully equipped kitchen. You'll also have access to a swimming pool, jacuzzi, fitness center, tennis court, and more.
