Top Holiday rentals in Key West

Find the Top Holiday rentals in Key West – 10+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-12 out of 12 holiday rentals
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Holiday home
8 adults
3 bedrooms
3 beds
MapView on map1.7 km from City Centre200 m from Duval Street
From   US$ 270 /nightSelect
  • Private entrance holiday home
  • On-site hot tub for relaxation
  • Pet-friendly accommodation
6 adults
2 bedrooms
3 beds
MapView on map1.8 km from City Centre100 m from Fury Water Adventures Key West
From   US$ 339 /nightSelect
  • Heated outdoor pool open year-round
  • Fully-equipped kitchens in apartments
  • Bicycle rentals for local exploration
  • Heated Pool
  • Private Villas
  • Outdoor Dining
2.1 km from City Centre400 m from San Carlos Institute Casa Cuba
From   US$ 709 /nightSelect
  • Heated outdoor swimming pool
  • Fully equipped kitchen in each villa
  • Adjacent to Duval Street shopping
Holiday home
  • Outdoor pool
  • Private entrance
  • Fully equipped kitchen
800 m from City Centre1000 m from Smathers Beach
From   US$ 408 /nightSelect
  • Private entrance to accommodations
  • Outdoor swimming pool for relaxation
  • Fully equipped kitchen in each unit
Apartment
  • Outdoor Pool
  • Sun Terrace
  • Barbecue Facilities
1000 m from City Centre600 m from Key West Cemetery
From   US$ 245 /nightSelect
  • Shared outdoor pool with waterfall
  • Tropical decor in individual rooms
  • Bicycle rentals available onsite
  • Private Entrance
  • Coffee Machine
  • Fishing Activities
1.9 km from City Centre200 m from San Carlos Institute Casa Cuba
From   US$ 64 /nightSelect
  • Private entrance for guest convenience
  • Close to popular attractions and beaches
  • Air-conditioned units with seating areas
  • Outdoor pool
  • Fitness centre
  • Hot tub
3.0 km from City Centre1.1 km from Kayak Kings Key West
From   US$ 414 /nightSelect
  • Outdoor swimming pool and hot tub
  • Two separate bedrooms and bathrooms
  • Private entrance for added privacy
  • City Views
  • Fully Equipped Kitchen
  • Private Entrance
2.0 km from City Centre100 m from San Carlos Institute Casa Cuba
From   US$ 627 /nightSelect
  • Private entrance with city views
  • Close to iconic attractions and beaches
  • Equipped kitchen with dishwasher
1.7 km from City Centre300 m from Ernest Hemingway House
From   US$ 390 /nightSelect
Situated 450 metres from South Beach, the Casa Havana @ Duval Square R22 also offers a swimming pool.
  • Outdoor Pool
  • Private Parking
  • Patio Dining
1.5 km from City Centre300 m from Duval Street
From   US$ 903 /nightSelect
  • Outdoor swimming pool for relaxation
  • Full kitchen with modern appliances
  • Pet-friendly private holiday home
Holiday home
1.7 km from City Centre300 m from Ernest Hemingway House
From   US$ 312 /nightSelect
Fort Zachary Taylor and Key West Butterfly and Nature Conservatory are respectively 1.7 km and 750 metres from the Windward Isle Villa.
Holiday home
  • Heated pool
  • Private entrance
  • Outdoor patio
1.9 km from City Centre200 m from Fury Water Adventures Key West
From   US$ 333 /nightSelect
  • Outdoor heated swimming pool
  • Close to Ernest Hemingway Home
  • Private entrance for added privacy