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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.

Sky Loft In Key West - Key West, FL
9.5 237 reviews

Sky Loft In Key West

house, Key West
This Key West home is conveniently located in the heart of the city, just a short walk from Simonton Street Beach and close to other popular attractions like Duval Street and the Ernest Hemingway Home and Museum. Guests consistently rate this rental excellent for its location, cleanliness, and overall experience.
The one-bedroom house offers 680 square feet of space, comfortably accommodating up to four guests. Enjoy amenities like a private pool, a patio, a fully equipped kitchen, and free Wi-Fi.

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.

Casa Havana | Old Town Condo W/ Pool & Balcony - Key West, FL
9.5 11 reviews

Casa Havana | Old Town Condo W/ Pool & Balcony

house, Key West
This Old Town Key West condo is located on the 1000 block of Duval Street, offering a 10-minute walk to downtown attractions like the Hemingway Home and Museum, and immediate proximity to Duval Square restaurants such as New York Pasta Garden and Origami Sushi, with walkable access to beaches.
This 2-bedroom, 2-bathroom condo accommodates up to 4 guests and features a fully equipped kitchen, in-unit washer/dryer, central air conditioning, free WiFi, a private deck and balcony, private garage parking, and access to a rooftop pool.
Cathouse Old Town Oasis Huge Heated Pool & Parking - Key West, FL
9.9 76 reviews

Cathouse Old Town Oasis Huge Heated Pool & Parking

house, Key West
This three-bedroom, two-bathroom Key West townhouse is situated in the White Street Gallery District, less than a mile from Duval Street and within walking distance of shops and restaurants.
The 3-level property features a 40-foot by 16-foot private pool, covered parking, private decks, and accommodates up to 10 guests with a fully equipped kitchen and stainless steel appliances.
Dos Casitas By Last Key Realty - Key West, FL
No reviews

Dos Casitas By Last Key Realty

house, Key West
Dos Casitas, near Key West's Southernmost Point, is a 5-minute walk from the landmark and a 4-minute walk from South Beach, offering easy access to Duval Street and the Ernest Hemingway Home and Museum.
This 2,570-square-foot Key West home boasts five bedrooms and five bathrooms, accommodating up to 27 guests, and includes a private pool, Jacuzzi, spa, and tennis court.
3 4 Tim E - Key West, FL
No reviews

3 4 Tim E

house, Key West
This 4-bedroom, 4-bathroom house is located 1.2 miles from Key West International Airport and is situated 2.3 miles from the Ernest Hemingway Home and Museum, 2.4 miles from Duval Street, and 2.5 miles from the Southernmost Point.
This property offers a private swimming pool, hot tub, air conditioning, Wi-Fi, and parking for up to 15 guests, with a kitchen equipped with a fridge, microwave, and dishwasher.

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

Kwss310 Sunrise Suites Panama Suite #310 - Key West, FL
8.8 210 reviews

Kwss310 Sunrise Suites Panama Suite #310

house, Key West
The Sunrise Suites Panama Suite #310 is located in Key West, just a short distance from the airport and a quick drive to the Southernmost Point. The property has received very good user and location ratings and an excellent cleanliness rating.
This two-bedroom suite offers a living room and a fully equipped kitchen. Enjoy the private balcony, swimming pool, jacuzzi, and access to the fitness center, tennis court, and spa.
Bahama Gardens - Cigar House - Key West, FL
No reviews

Bahama Gardens - Cigar House

house, Key West
House rental. This accommodation is based in Key West.
Facilities and services include a swimming pool, an iron and a barbecue. Take advantage of the air conditioning in this house!
Kwss202 Sunrise Suites - Big Kahuna Suite 202 - Key West, FL
No reviews

Kwss202 Sunrise Suites - Big Kahuna Suite 202

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.
Paradise Found Cayo Hueso - Key West, FL
9.3 229 reviews

Paradise Found Cayo Hueso

house, Key West
Paradise Found Cayo Hueso is located in Key West, just a short drive from the airport and popular beaches like Smathers Beach. This apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The 1,360 square foot apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private balcony with ocean views, a swimming pool, a fitness center, and a tennis court, offering a range of activities and comforts for a relaxing stay.

Neighborhoods and points of interest in Key West, FL

Best Key West, FL houses with a kitchen

Casita Angelita By Last Key Realty - Key West, FL
10 1 review

Casita Angelita By Last Key Realty

house, Key West
Casita Angelita, a Key West house rental, is centrally located, a 12-minute walk from South Beach and an 11-minute walk from Fort Zachary Taylor Historic State Park.
This 1,300-square-foot vacation home features two bedrooms, two bathrooms, sleeps up to 11 guests, and includes a private pool, spa, and tennis court, plus free Wi-Fi and parking.
Tropical Dreaming By Avantstay | 4 Blks To Beach! Private Pool! - Key West, FL
No reviews

Tropical Dreaming By Avantstay | 4 Blks To Beach! Private Pool!

house, Key West
This Key West vacation home is located in Old Town, a short stroll to Duval Street and 0.25 miles from the Atlantic Ocean.
This family-friendly rental sleeps six guests and features two bedroom suites, a private pool with a covered porch, an outdoor shower, a wet bar, and a full kitchen.
Seagull Suite | Inviting Studio, Steps From Duval - Key West, FL
No reviews

Seagull Suite | Inviting Studio, Steps From Duval

studio, 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.
Hemingways Atlantic Retreat - Key West, FL
No reviews

Hemingways Atlantic Retreat

house, Key West
House rental listing. This accommodation is located in Key West.
Facilities and services include a fitness center, air conditioning and a fridge. Take advantage of the Free Parking with this accommodation in Key West!

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.

Hidden Oasis Colony - Key West, FL
No reviews

Hidden Oasis Colony

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.

113 M² House ∙ 2 Bedrooms ∙ 6 Guests - Key West, FL
9.1 21 reviews

113 M² House ∙ 2 Bedrooms ∙ 6 Guests

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

46 M² House ∙ 1 Bedroom ∙ 3 Guests

house, Key West
Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-friendly - Key West, FL
9.6 17 reviews

Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-friendly

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.

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

Southernmost Hospitality V By Last Key Realty

house, Key West
Duchess Of Catherine By Last Key Realty - Key West, FL
No reviews

Duchess Of Catherine By Last Key Realty

house, Key West
Kingfish Keep - Key West, FL
9.0 2 reviews

Kingfish Keep

house, Key West
Southern Palms - Key West, FL
9.0 585 reviews

Southern Palms

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.

Paradise Found Cayo Hueso - Key West, FL
9.3 229 reviews

Paradise Found Cayo Hueso

house, Key West

Best Key West, FL houses with air conditioning

Botanical Island Delight - Key West, FL
8.0 4 reviews

Botanical Island Delight

house, Key West
Charming Hideaway With Shared Pool - Inviting Location And Unique Amenities - Key West, FL
No reviews

Charming Hideaway With Shared Pool - Inviting Location And Unique Amenities

house, Key West
Free Boat Slip - Waterfront Condo - Key West Pool - Key West, FL
No reviews

Free Boat Slip - Waterfront Condo - Key West Pool

house, Key West
Rose Lane Villas - Key West, FL
9.2 567 reviews

Rose Lane Villas

house, Key West
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