Resort holiday rentals in Key West

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Top-rated resort stays in Key West

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Superhost

Resort in Key West

4.89 out of 5 average rating, 9 reviews

Parrot's Perch

The Parrot’s Perch (formerly Zeke’s Retreat) is a sun filled suite with soaring ceilings features a living room with a queen sleeper sofa, a wraparound porch with a hammock, a kitchenette with a convection \microwave oven and a bedroom with a king size bed with private balcony overlooking the palm trees. Sleeps 4 people. Complimentary breakfast included. Enjoy 3 pools, wifi, and smart TVs. Very limited paid parking available onsite on a first come first serve basis.

Superhost

Resort in Key West

4.8 out of 5 average rating, 10 reviews

Katie's Kottage

Relax in this private cottage located in the heart of Old Town Key West. The cottage sports 2 private bedrooms with queen beds, 2 bathrooms, a queen pullout couch, full living room and kitchen, & deck area that surrounds one of our pools. Enjoy our daily complimentary breakfast, 3 pools, wifi, and TV. Perfect for a group of up to 6 or families! We have paid parking first come first serve, or you can find free street parking.

Resort in Key West

5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe - Key West - Amazing Resort!

Atlantic ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Deluxe amenities include full kitchen, dining area, living room with TV and stereo CD player, furnished balcony and wireless Internet

Resort in Key West

4.73 out of 5 average rating, 52 reviews

Charming 2 Bedroom Suite Beach Resort

Our private tropical paradise, reminiscent of days gone by, sits quietly and serenely on the Atlantic side of Key West. Here you will find a blend of old island architecture, lush vegetation and quiet walkways flowing onto bright white verandahs. Each of our layouts offers its own touch of uniqueness, be it a high-pitched ceiling, a private balcony or a spectacular panoramic view.

Resort in Key West

4.83 out of 5 average rating, 12 reviews

1BR Condo Banyan Tree, KeyWest Unit 505/701

With pools, a hot tub, Tiki Bar, BBQ grills, and a full kitchen in each unit you can enjoy the lush private surroundings and still be close to the heart of Key West, Hemingway Museum, Sloppy Joe's, 1 block off Duval. ONLY dates on calendar are available. This 1BR Listing covers unit 701 in Oct and 505 in July. Steps up to condo. Steps up to loft.

Resort in Key West

4.88 out of 5 average rating, 16 reviews

1BR #405 Banyan Resort Key West, FL

With pools, a hot tub, Tiki Bar, BBQ grills, and a kitchen in each unit you can enjoy the lush private surroundings and still be close to the heart of Key West, Hemingway Museum, Sloppy Joe's, 1 block off Duval. ONLY dates on calendar are available. This unit has a large deck with a commanding view of the property from 3 stories up.