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Key West, FL villas
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1524 Villa rentals in Key West, FL

Browse Waterfront Vacation Homes in Key West, FL

Experience relaxing beach-town vibes at these seaside vacation homes in Key West, FL, located short distances from the local shore.

Petes East Cottage - Key West, FL
9.3 3 reviews

Petes East Cottage

house, Key West
Petes East Cottage, a Key West house rental, is a 6-minute walk from the Ernest Hemingway Home and Museum, 0.4 miles from Duval Street, and a short stroll from South Beach, offering easy access to Key West's city center and nearby beaches like Fort Zachary Taylor State Park Beach and Higgs Beach.
This 700-square-foot Key West vacation home features two bedrooms, one bathroom, accommodates seven guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, a garden, a tennis court, free Wi-Fi, and parking.

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.

Kw230 Last-minute - Key West, FL
No reviews

Kw230 Last-minute

house, Key West
This Key West house is located in the city center, a 7-minute walk to Simonton Street Beach and 656 feet from the Key West Aquarium.
This 1600 square foot residence accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a private swimming pool, barbecue facilities, and a fully equipped kitchen with a dishwasher and microwave.
Absolutely Paradise Awaits You By Rent Key West - Key West, FL
9.8 106 reviews

Absolutely Paradise Awaits You By Rent Key West

house, Key West
This 3-bedroom, 2-bathroom townhome offers prime Old Town Key West lodging, located just one block from Duval Street and near the intersection of Truman & Simonton Streets.
This residence accommodates up to 8 guests with a private heated pool, a fully equipped modern kitchen, and Caribbean-inspired interiors, ideal for enjoying year-round island living.
Inviting Deck And Shared Pool - Charming Studio Retreat - Key West, FL
No reviews

Inviting Deck And Shared Pool - Charming Studio Retreat

cottage, Key West
This studio suite in the historic Colony on Olivia Street is located in Old Town Key West, just 0.1 miles from Duval Street and within easy walking distance of shops and restaurants.
This family-friendly cottage accommodates up to 4 guests and features a King bed, a couch, a kitchenette, air conditioning, internet, a shared swimming pool, and a garden, with a 10:00 AM check-out time.
95 M² House ∙ 2 Bedrooms ∙ 4 Guests - Key West, FL
No reviews

95 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Key West
Passover Cottage, a private house in Key West, is located in a prime residential area just a short walk to the Ernest Hemingway Home and Museum and Southernmost Point, with convenient access to Duval Street and beaches.
This 1010 square foot cottage accommodates up to 4 guests, featuring 2 bedrooms, 2 bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, Wi-Fi, a private swimming pool, and a patio with a gas grill.

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 are the best villa rentals in Key West, FL?

    Among the villa rentals in Key West, FL, Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas are the most popular ones.

  • 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?

    Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas are the best villa rentals with a pool in Key West, FL.

  • What are the best activities 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?

    The best villa rentals with a jacuzzi in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas.

  • 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?

    The best villa rentals for families and kids in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas.

  • 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?

    The best pet friendly villa rentals in Key West, FL are Leaward Isle Island Retreat, Secret Courtyard Cottage and Pescado Penthouse On Duval.

  • 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?

    Leaward Isle Island Retreat, Secret Courtyard Cottage and Key West Villas 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.

Popular destinations

Best Key West, FL villas and beach houses with jacuzzi

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 within a mile of Rest Beach and Higgs Beach. It boasts consistently high ratings for cleanliness, location, and overall user experience.
This two-bedroom, two-bathroom unit comfortably accommodates up to six guests. Enjoy a range of amenities including a pool, jacuzzi, fitness center, tennis court, and a fully equipped kitchen.
Paris Mango - Key West, FL
No reviews

Paris Mango

house, Key West
Paris Mango is a residence located 1.2 miles from Key West International Airport, offering convenient access to attractions such as the Ernest Hemingway Home and Museum (2.3 miles), Duval Street (2.4 miles), and the Southernmost Point (2.6 miles).
This pet-friendly accommodation accommodates up to 15 guests with four bathrooms, a full kitchen featuring a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, spa, and a terrace or balcony, with complimentary WiFi and private parking provided.
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 popular attractions like Duval Street and Mallory Square. This vacation rental has excellent ratings for location, cleanliness, and user experience.
The suite has two bedrooms and can accommodate up to six guests. Enjoy the amenities like a private patio, swimming pool, and fitness center, perfect for relaxing and staying active during your Key West getaway.
Botanical Island Delight - Key West, FL
8.0 4 reviews

Botanical Island Delight

house, Key West
Botanical Island Delight, a Key West vacation home, offers convenient access to Smathers Beach (a 4-minute walk), Southernmost Point (1.6 miles), the Ernest Hemingway Home and Museum (2 miles), and Key West International Airport (1.2 miles).
This two-bedroom, two-bathroom rental sleeps seven guests and boasts a private pool, Jacuzzi, tennis court, fitness center, and complimentary Wi-Fi, along with on-site parking and tour organization services.

Neighborhoods and points of interest in Key West, FL

Best Key West, FL houses with a kitchen

Suncoast House -Pool & Boat Dock - Key West, FL
9.7 57 reviews

Suncoast House -Pool & Boat Dock

house, Key West
This luxurious Key Haven home, a short drive from Key West's downtown and attractions, offers a private dock accommodating boats up to 50 feet.
The 3,550-square-foot property boasts five bedrooms and 5.5 bathrooms, accommodating up to 14 guests, and features a private pool, fenced yard, fully equipped kitchen, and access to a nearby fitness center.
The Crestwood House - Private Heated Pool & Parking - Key West, FL
10 2 reviews

The Crestwood House - Private Heated Pool & Parking

house, Key West
This 2900 square foot vacation home in Key West is located approximately 5.2 miles from the Ernest Hemingway Home and Museum and 5.3 miles from Duval Street.
This 6-bedroom, 7-bathroom house accommodates up to 22 guests and features a private heated outdoor swimming pool, a garden, a fitness center, and on-site parking with complimentary high-speed WiFi.
Crawl To Duval W/ Hot Tub - Key West, FL
8.6 6 reviews

Crawl To Duval W/ Hot Tub

house, Key West
This Key West house is located in Old Town, just a short walk from both South Beach and Fort Zachary Taylor State Park Beach, putting you close to the island's best beaches and the vibrant city center. The property consistently receives high ratings for location, cleanliness, and overall experience.
The 2-bedroom vacation rental comfortably sleeps up to 6 guests and offers a spacious 900 square feet of living space. This Key West home features a fully equipped kitchen, private hot tub, outdoor dining area, and free parking, providing everything you need for a relaxing and enjoyable stay.
115 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
No reviews

115 M² House ∙ 2 Bedrooms ∙ 6 Guests

house, Key West
Casa Havana, situated in Duval Square on the 1000 block of Duval Street, offers direct walking access to downtown Key West attractions, including the Southernmost Point, and is located above New York Pasta Garden and Origami Sushi, approximately a 0.5 mile walk from the heart of the city. This 1240 square foot house accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a private deck, a balcony, a private garage parking spot, a washer/dryer, central air conditioning, and access to a rooftop pool.

Guest-Favorite Luxury Vacation Homes in Key West, FL

These upscale vacation homes in Key West, FL provide the perfect blend of premium amenities and a highly desirable prime location.

The Sophisticated Sandpiper At Old Town - Key West, FL
10 4 reviews

The Sophisticated Sandpiper At Old Town

house, Key West

Choose the Right Family-Friendly Holiday Houses in Key West, FL

Choosing a family vacation home in Key West, FL provides plenty of room to spread out and the perfect space to plan your day with the kids.

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

Tropical Landscaping And Private Deck - Charming Coastal Escape

cottage, Key West
The Rigby House - Pool, One Block From Duval St - Key West, FL
No reviews

The Rigby House - Pool, One Block From Duval St

house, Key West
Southern Palms - Steps To Duval With Private Pool - Key West, FL
No reviews

Southern Palms - Steps To Duval With Private Pool

house, Key West
Passover Cottage | Private Pool & Ideal Key West Location - Key West, FL
No reviews

Passover Cottage | Private Pool & Ideal Key West Location

house, Key West

Find the Best Pet-Friendly Vacation Homes in Key West, FL

Traveling with your dog? These Key West, FL vacation homes are pet-ready, so you and your four-legged companion can relax from the moment you arrive.

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock - Key West, FL
9.4 11 reviews

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock

house, Key West
~Margarita Cottage~ Bask In Sunshine And Lounge By Your Pool In Paradise. - Key West, FL
9.6 15 reviews

~Margarita Cottage~ Bask In Sunshine And Lounge By Your Pool In Paradise.

cottage, Key West
Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo - Key West, FL
9.1 18 reviews

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo

house, Key West
Banana Breeze - Key West, FL
No reviews

Banana Breeze

house, Key West

Explore Holiday Houses with Wellness in Key West, FL

Discover spa access at these waterfront vacation homes in Key West, FL, ensuring wellness by the water is never an afterthought.

New The Cottage At James House - Key West, FL
8.5 8 reviews

New The Cottage At James House

house, Key West

Best Key West, FL houses with air conditioning

Kw31c Jasmine Suite - Key West, FL
No reviews

Kw31c Jasmine Suite

house, Key West
American Shoal Light Suite - Key West, FL
No reviews

American Shoal Light Suite

house, Key West
Rooftop Penthouse - Key West, FL
9.8 4 reviews

Rooftop Penthouse

house, Key West
Colony Calypso - Key West, FL
No reviews

Colony Calypso

cottage, Key West
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