Villas and Holiday homes in Key West, FL

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Key West, FL holiday homes
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1524 Villa rentals in Key West, FL

Best Key West, FL villas and holiday homes with air conditioning

112 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.6 9 reviews

112 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
This Key West townhouse, situated in the Truman Annex, is steps from Harry S. Truman's Little White House and within 0.32 kilometres of Duval Street.
The 112-square-metre property offers a two-bedroom, two-and-a-half-bathroom layout, sleeping up to six guests, and includes a kitchen with fridge, freezer, and dishwasher, air conditioning, a private porch, and access to a community swimming pool; nearby attractions include Mallory Square and Fort Zachary Taylor State Park.
Nassau Suite Just Steps To Duval Tropical Oasis  Quiet Location Downtown - Key West, FL
9.2 442 reviews

Nassau Suite Just Steps To Duval Tropical Oasis Quiet Location Downtown

apartment, Key West
This charming house is located in Old Town Key West, a short stroll from Duval Street and the Ernest Hemingway Home and Museum. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house offers one bedroom and one bathroom, accommodating up to four guests comfortably within its 79 square metres of space. Guests can enjoy a range of amenities, including a swimming pool, tennis court, and a fully equipped kitchen, making it ideal for a relaxing and enjoyable stay.
St John - Downtown Waterfront Penthouse Pool Parking Dock - Key West, FL
9.3 3 reviews

St John - Downtown Waterfront Penthouse Pool Parking Dock

house, Key West
This Key West penthouse, situated 1.8km from both the Ernest Hemingway Home and Museum and Duval Street, and 1.9km from Key West International Airport, offers stunning sea views from its direct waterfront location.
The 186 square metre property boasts four bedrooms, four bathrooms, sleeps 24 guests, includes a private pool, free Wi-Fi, and a fully equipped kitchen; nearby activities include cycling.
Middle Sunset - Key West, FL
No reviews

Middle Sunset

house, Key West
This Key West property, Middle Sunset, is situated 1.5km from the Ernest Hemingway Home and Museum, 1.4km from Duval Street, and 2km from Key West International Airport.
The 93 square metre house sleeps 11 guests and boasts three bathrooms, a private pool, tennis court, fitness centre, and free Wi-Fi; massage services are also available on-site.

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.

Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 20 - Key West, FL
No reviews

Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 20

house, Key West
House rental. Your accommodation will be located in Key West.
Facilities and services: a washing machine, free parking and a barbecue. Take advantage of the air conditioning in this house in Key West.
Key West's Best - Key West, FL
9.4 6 reviews

Key West's Best

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.
Leaward Isle Island Retreat - Key West, FL
9.8 2674 reviews

Leaward Isle Island Retreat

house, Key West
This Key West property is a short walk from Smathers Beach, a popular stretch of sand known for its beautiful sunsets and water activities, and just a short distance from Rest Beach. The property boasts excellent user, location and cleanliness ratings.
This spacious house offers a fully equipped kitchen, air conditioning, free Wi-Fi and a private balcony with sea views. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, spa, fitness centre, tennis court, and a bar.
Conch In The Treetops By Last Key Realty - Key West, FL
9.3 3 reviews

Conch In The Treetops By Last Key Realty

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.

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 are the best holiday homes in Key West, FL?

  • 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?

  • What are the best activities 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?

    The best holiday homes with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Key West Villas and Two Duval Street Condos W Parking And Pool.

  • 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.

Popular destinations

Best Key West, FL villas and holiday homes with a kitchen

Sandpiper On The Ocean - Key West, FL
No reviews

Sandpiper On The Ocean

house, Key West
House. This accommodation is located in Key West.
Facilities and services: an iron, a swimming pool and a jacuzzi. Enjoy free parking with this accommodation in Key West!
Nautical Wheeler - Key West, FL
No reviews

Nautical Wheeler

house, Key West
Nautical Wheeler, a Key West holiday home near Key West International Airport, is situated approximately 3.9 kilometres from the Ernest Hemingway Home and Museum and Duval Street.
This three-bathroom property sleeps fifteen guests and boasts a private pool, spa, terrace, free Wi-Fi, and free private parking, plus massage services are available on-site.
3 Bedroom Duval Street Penthouse - Key West, FL
10 7 reviews

3 Bedroom Duval Street Penthouse

house, Key West
This luxury penthouse is situated directly on Duval Street in Old Town Key West, offering immediate access to restaurants, shops, and theatres within 100 metres.
This 204 square metre residence accommodates up to eight guests across three bedrooms, each with a private balcony, and features a private backyard with a swimming pool and a rooftop sun deck with views over Duval Street.
Seaside Retreat: Waterfront Home With Private Heated Pool & Lush Landscaping - Key West, FL
9.6 95 reviews

Seaside Retreat: Waterfront Home With Private Heated Pool & Lush Landscaping

apartment, Key West
This Key West Northside Resort property offers a spacious 218 square metre (2345 sq ft) house, ideally located within 4.8 kilometres of Duval Street, Mallory Square, and other Key West attractions.
The four-bedroom residence sleeps eight guests and boasts a private pool, Jacuzzi, fully equipped kitchen, and concierge services; barbecue facilities are also available on-site.

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.

Evershore House -Pool, Parking, Dock! - Key West, FL
9.9 117 reviews

Evershore House -Pool, Parking, Dock!

house, Key West
This Key Haven waterfront property, a short distance from Key West's attractions, offers a private pool and dock accommodating boats up to 15.24 metres.
The 267 square metre house boasts four bedrooms, four bathrooms, sleeping up to twelve guests, and features a fully equipped kitchen, a private gated yard, and complimentary access to the nearby FYT fitness centre.
Sailor's Son - Key West, FL
No reviews

Sailor's Son

house, Key West
Sailor's Son, a Key West property, is conveniently located 1.9km from Key West International Airport, and 3.9km from both the Ernest Hemingway Home and Museum and Duval Street.
This four-bathroom house sleeps 15 guests and boasts a swimming pool, jacuzzi, spa, fitness centre, and private parking, alongside a well-equipped kitchen and complimentary Wi-Fi.
Dockside Daydreams By Last Key Realty - Key West, FL
No reviews

Dockside Daydreams By Last Key Realty

house, Key West
Dockside Daydreams is a Key West property located just 1 kilometre from Key West International Airport and a short drive from attractions including the Southernmost Point, Ernest Hemingway Home and Museum, and Duval Street.
This 65 square metre holiday home offers two bedrooms, two bathrooms, sleeps up to 11 guests, and boasts a swimming pool, Jacuzzi, spa, tennis court, and free Wi-Fi.
227 M² House ∙ 4 Bedrooms ∙ 8 Guests - Key West, FL
No reviews

227 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Key West
This Key West property is centrally located, offering convenient access to shops, restaurants, nightlife, and the beach within a 1.6 kilometre radius.
This 227 square metre house sleeps eight guests and features a private pool, four bedrooms, four bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and on-site parking.

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.

The Gato Room At Inn On Fleming Key West! - Key West, FL
9.0 1 review

The Gato Room At Inn On Fleming Key West!

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.

Coconut Palm - Key West, FL
9.0 577 reviews

Coconut Palm

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.

Sparkling Pool And Ample Lounging Space - Stunning Tropical Retreat - Key West, FL
No reviews

Sparkling Pool And Ample Lounging Space - Stunning Tropical Retreat

house, Key West
Charming Deck And Inviting Living Space - Serene Coastal Retreat - Key West, FL
No reviews

Charming Deck And Inviting Living Space - Serene Coastal Retreat

cottage, Key West
127 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.5 30 reviews

127 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
Tropical Landscaping And Private Deck - Charming Coastal Escape - Key West, FL
No reviews

Tropical Landscaping And Private Deck - Charming Coastal Escape

cottage, 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.

Kwss310 Sunrise Suites Panama Suite #310 - Key West, FL
8.7 420 reviews

Kwss310 Sunrise Suites Panama Suite #310

house, Key West
Catherine House - Key West, FL
10 1 review

Catherine House

house, Key West
Crawl To Duval W/ Hot Tub - Key West, FL
8.6 7 reviews

Crawl To Duval W/ Hot Tub

house, Key West
Chagall's Corner - Key West, FL
No reviews

Chagall's Corner

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.

Upper Bayview North - Key West, FL
No reviews

Upper Bayview North

house, Key West
Casa Victoria By Last Key Realty - Key West, FL
No reviews

Casa Victoria By Last Key Realty

house, Key West
Poolside Cottage #411 - Key West, FL
9.8 224 reviews

Poolside Cottage #411

house, Key West
122 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.3 19 reviews

122 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
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