Holiday Homes in Key West

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Featured Holiday Homes in Key West

Enjoy cooking in this well-equipped kitchen with a central island and bar stools, offering a view of the adjacent dining area.

"Outstanding property! Cannot recommend highly enough!"

Relax in an outdoor space with a bed, barbecue grill, and lush greenery.

"Property was amazing, exactly what is shown in the listing, beds were extremely comfortable, will stay again"

Relax by the pool surrounded by lush foliage and enjoy a hot tub on the deck.

"This property is perfectly located near Duval street and within walking distance to the marina. A perfect location for those wanting to shop and enjoy the amenities the marina has to offer. We can’t wait to go back. "

Relax in a serene pool area surrounded by lush greenery and palm trees, complete with lounge chairs and umbrellas.

"Good spot for longer trips and never a problem parking. Easy trip to Old Town and the Lower Keys for other activities. We always stay at least a week and take our pup, so its great for us. Close to The Perry Hotel for both a great Happy Hour and fine diningDining"

includes taxes & fees

2 Aug - 3 Aug

"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"

Relax and socialize in this serene patio area, featuring a large table and comfortable seating.

"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "

includes taxes & fees

27 July - 28 July

Enjoy a spacious living area with a kitchen, dining, and seating space, featuring a sofa, wooden table, and staircase.

"We had 3 couples and the location was great. The house was very nice. "

Relax by the pool in a serene backyard oasis with a wooden deck and shaded gazebo.

"We loved the house. From the location, to ambiance and heated pool- it was all amazing! We didn’t cook at all and spent most of our time out and about, but we used the pool day and night. We had 2 couples and 2 additional friends and it was the perfect amount of space and privacy! Would highly recommend this spot and nearby is a cute little bike shop to easily rent a bike cruiser or golf cart for your time! "

Stunning hallway with ornate mirror, modern chandelier, and large window.

"The place was everything that was advertised! Great weather, location, cottage and friends - what could be better!!"

Relax in a spacious living area with a dining table, sofa, and comfortable seating.

"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."

Relax by the pool surrounded by lush tropical vegetation and a covered patio area.

"Great place to stay for our spring trip as a family of 3. "

includes taxes & fees

5 Aug - 6 Aug

Enjoy a well-appointed kitchen and living area with stainless steel appliances, a dining table, and a comfortable sofa.

"Wonderful stay!"

Relax by the serene pool surrounded by lush greenery and a deck with seating area.

"Great location "

"Property was clean and comfortable with everything we needed. Only complaint is the late check in time."

Relax by the serene pool surrounded by lush greenery and a comfortable seating area.

"We had a great time and loved the property "

Relax on a crescent-shaped beach with turquoise waters and lush green surroundings.

"Perfect place to stay. Great location. "

includes taxes & fees

11 Aug - 12 Aug

Relax in a serene outdoor space surrounded by lush greenery and a central fountain.

"We had a really great time in Key West and much of it was due to the accommodations, as it was clean, offered every amenity and then some but most importantly was the location! The Courtyard was serene and quiet, and you didn't feel like you were just steps away from the activity of Duval Street and could just about walk to everything! We were REALLY happy we stayed here!! "