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

Atlantis House Suites - Key West, FL
No reviews

Atlantis House Suites

house, Key West
Atlantis House Suites offers a two-bedroom, two-bathroom property near Rest Beach in Key West, Florida, less than 2km from Key West International Airport and within a 3km radius of the Ernest Hemingway Home and Duval Street.
This 93 square metre self-catering house, sleeping up to seven guests, boasts free Wi-Fi, air conditioning, a fully equipped kitchen, and an outdoor dining area with sea views.
New Grenada Suite - Parking Pool & Pets 209 - Key West, FL
9.1 115 reviews

New Grenada Suite - Parking Pool & Pets 209

house, Key West
The NEW Grenada Suite is located in Key West, just a short drive from Duval Street and Mallory Square, offering a peaceful retreat while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
This two-bedroom property can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities including a private pool, a jacuzzi, a fully equipped kitchen, and a fitness centre, ensuring a comfortable and enjoyable stay.
New The Cottage At James House - Key West, FL
8.5 8 reviews

New The Cottage At James House

house, Key West
New The Cottage at James House, a centrally located Key West holiday home, is a short walk (approx. 0.8km) from the Key West Aquarium, Mallory Dock, and Simonton Street Beach.
This 56 square metre self-catering property boasts one bedroom, one bathroom, sleeps four guests, and features a private patio, swimming pool access, free Wi-Fi, and a fully equipped kitchen including a fridge and microwave.
New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool - Key West, FL
8.2 19 reviews

New Casa Caribe By Brightwild- Two-story Condo Rooftop Pool

house, Key West
This two-bedroom Key West condo, a short walk from South Beach and Duval Street, is centrally located less than 1.6km from the Southernmost Point buoy.
The 116 square metre property boasts a rooftop pool, fully equipped kitchen, three bathrooms, and accommodates up to six guests, offering free Wi-Fi and air conditioning.

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.

Atlantic Paradise Found - Key West, FL
9.6 237 reviews

Atlantic Paradise Found

house, Key West
This apartment in Key West is conveniently located just a short walk from Smathers Beach and Rest Beach, offering easy access to the beautiful beaches and the relaxed atmosphere of this popular destination. It boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is spacious, with 126 square metres of living space and comfortably accommodates up to 6 guests. It comes with a range of amenities including a fully equipped kitchen, a swimming pool, a jacuzzi, a tennis court and a fitness centre, providing everything you need for a relaxing and enjoyable holiday.
Kw41 Amelia House - Key West, FL
No reviews

Kw41 Amelia House

house, Key West
This Key West holiday cottage, KW41 Amelia House, offers exceptional proximity to Southernmost Point, a 5-minute walk, and South Beach, a 4-minute walk, placing it conveniently near Mallory Dock (1.5 kilometres) and the San Carlos Institute Casa Cuba (800 metres).
This air-conditioned property spans 78 square metres, accommodates up to 11 guests across 3 bedrooms and 2 bathrooms, and features a private hot tub for relaxation, with entertainment provided by cable TV.
Hemingways Atlantic Retreat - Key West, FL
9.2 129 reviews

Hemingways Atlantic Retreat

house, Key West
This apartment is located in Key West, a short walk from Smathers Beach and close to Rest Beach, offering easy access to the island's beautiful beaches and vibrant atmosphere. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment is spacious, with two bedrooms and two bathrooms, ideal for families or groups of up to six guests. It also boasts a range of amenities, including a swimming pool, a Jacuzzi, a fitness center, and a tennis court, ensuring a comfortable and enjoyable stay.
The Grande Vista - Key West, FL
9.1 203 reviews

The Grande Vista

house, Key West
The Grande Vista apartment is located in Key West, just a short walk from Smathers Beach and Rest Beach, with Higgs Beach also within easy reach. The apartment has received very good user ratings, and excellent location and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, and can accommodate up to six guests. It is well-equipped with amenities such as a kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a sauna, a fitness centre, a tennis court, parking, and internet access.

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

Sunset South - Key West, FL
No reviews

Sunset South

house, Key West
Sunset South, a Key West property, is conveniently located near Duval Street and the Ernest Hemingway Home and Museum, a short 2.25 km walk from Rest Beach.
This one-bathroom house sleeps seven guests and boasts a swimming pool, tennis court, fitness centre, and private parking, plus a well-equipped kitchen and balcony with city views; massage services are available on-site.
Osprey Colony - Key West, FL
No reviews

Osprey Colony

house, Key West
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.
**Casa Amarilla** Old Town Cottage &  Pool + Last Key White Glove Service... - Key West, FL
10 107 reviews

**Casa Amarilla** Old Town Cottage & Pool + Last Key White Glove Service...

apartment, Key West
This Key West Historic District property is located steps from the City Zoo Gallery and Duval Street, with South Beach and Florida Keys beaches within an 800-metre radius.
This 112-square-metre house boasts three bedrooms sleeping six, a private pool, tennis courts, and a fully equipped kitchen including a dishwasher, all within a beautifully maintained garden; free Wi-Fi is also provided.
Passover Cottage | Private Pool & Ideal Key West Location - Key West, FL
No reviews

Passover Cottage | Private Pool & Ideal Key West Location

house, Key West
Passover Cottage, a two-bedroom dwelling in Key West, is centrally located within 300 metres of the Ernest Hemingway Home and Museum and the Southernmost Point.
This family-friendly accommodation offers a private swimming pool, air conditioning, a fully equipped kitchen with a dishwasher, and on-site parking, with a maximum guest capacity of four.

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.

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.
Passover Cottage - Key West, FL
No reviews

Passover Cottage

house, Key West
Passover Cottage, a Key West holiday home, enjoys a central location, less than 2.25km from South Beach and within 1.6km of Duval Street, offering easy access to the Ernest Hemingway Home and Museum and the Southernmost Point.
This two-bedroom, two-bathroom property sleeps seven, boasting a private pool, fully equipped kitchen with dishwasher, air conditioning, and proximity to Mallory Dock and Key West International Airport.
Colony Calypso - Key West, FL
No reviews

Colony Calypso

cottage, Key West
Colony Calypso, a one-bedroom bungalow within The Colony collection, is located in Old Town, Key West, a mere 320 metres from Duval Street.
This family-friendly accommodation offers air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and access to a communal swimming pool, spa, and tennis court, accommodating up to four guests.
Abaco - Large Waterfront 2x2 End Unit With Boat Slip - Key West, FL
8.8 5 reviews

Abaco - Large Waterfront 2x2 End Unit With Boat Slip

house, Key West
This Key West waterfront property, a short walk from Rest Beach and 1.9km from South Beach, offers direct access to a private boat slip and is 2km from Key West International Airport.
The 121 square metre house boasts two bedrooms, two bathrooms, a fully equipped kitchen, a private patio with sea views, free Wi-Fi, on-site parking, and accommodates up to 11 guests, with free bicycle use available.

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.

Yellowfin Ledge - Key West, FL
10 4 reviews

Yellowfin Ledge

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.

Paradise Place By Avantstay - Key West, FL
9.2 120 reviews

Paradise Place By Avantstay

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.

46 M² House ∙ 1 Bedroom ∙ 3 Guests - Key West, FL
9.3 57 reviews

46 M² House ∙ 1 Bedroom ∙ 3 Guests

house, Key West
Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven - Key West, FL
No reviews

Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven

cottage, Key West
Beachfront 2bdr Condo, Pool & Hot Tub W/ Ocean Views | Papaya Place By Avantstay - Key West, FL
No reviews

Beachfront 2bdr Condo, Pool & Hot Tub W/ Ocean Views | Papaya Place By Avantstay

house, Key West
42 M² House ∙ 1 Bedroom ∙ 4 Guests - Key West, FL
9.4 26 reviews

42 M² House ∙ 1 Bedroom ∙ 4 Guests

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.

Coastal Comfort - Key West, FL
8.0 1 review

Coastal Comfort

house, Key West
~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street. - Key West, FL
9.9 470 reviews

~ Petite Maison ~ 2 King Ensuite Bedrooms On A Quiet Lane Near Duval Street.

apartment, Key West
Southernmost Hospitality V By Last Key Realty - Key West, FL
No reviews

Southernmost Hospitality V By Last Key Realty

house, Key West
Bayview Retreat - Key West, FL
No reviews

Bayview Retreat

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.

New Rose Retreat - Pool Parking - Key West, FL
No reviews

New Rose Retreat - Pool Parking

house, Key West
Cohiba At Azul Mansion Key West - Key West, FL
10 2 reviews

Cohiba At Azul Mansion Key West

house, Key West
Ocean Hideaway On The Atlantic - Key West, FL
No reviews

Ocean Hideaway On The Atlantic

house, Key West
Petes Cottages - Key West, FL
10 1 review

Petes Cottages

house, Key West
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