Top Holiday rentals in Key West

Find the Top Holiday rentals in Key West – 20+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 25 holiday rentals
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6 adults
3 bedrooms
3 beds
MapView on map2.1 km from City Centre400 m from San Carlos Institute Casa Cuba
From   US$ 246 /nightSelect
  • Heated outdoor swimming pool
  • Fully equipped kitchen in each villa
  • Adjacent to Duval Street shopping
Holiday home
6 adults
2 bedrooms
4 beds
MapView on map800 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
Holiday home
  • Hot tub
  • Cycling
  • Patio
1.7 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
  • 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
  • Heated Pool
  • Bicycle Rentals
  • Outdoor Jacuzzi
1.8 km from City Centre100 m from Fury Water Adventures Key West
From   US$ 561 /nightSelect
  • Heated outdoor pool open year-round
  • Fully-equipped kitchens in apartments
  • Bicycle rentals for local exploration
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
Apartment
  • Outdoor Pool
  • Fishing
  • Air Conditioning
1.9 km from City Centre200 m from Duval Street
From   US$ 399 /nightSelect
  • Heated outdoor swimming pool
  • Fishing activities nearby
  • Private balconies in select rooms
5.7 km from City Centre
From   US$ 325 /nightSelect
You can relax by a swimming pool in the intimate Grand Marina Suite By Brightwild-Waterfront Condo, located at a 4.4 km distance from Smathers Beach.
  • 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
Holiday home
1.8 km from City Centre100 m from Ernest Hemingway House
From   US$ 879 /nightSelect
This villa in the Duval district is composed of 3 bedrooms, a kitchen and 2 bathrooms.
Apartment
2.0 km from City Centre200 m from Fury Water Adventures Key West
From   US$ 470 /nightSelect
The Traveler'S Palm is situated in the museum Duval district, 10 minutes' drive from Key West International airport.
  • 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
  • Heated pool
  • Fitness centre
  • Hot tub
3.0 km from City Centre1.1 km from Kayak Kings Key West
From   US$ 122 /nightSelect
  • Private entrance with accommodation privacy
  • Heated outdoor swimming pool available
  • On-site fitness centre for workouts
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
1.7 km from City Centre200 m from Ernest Hemingway House
From   US$ 850 /nightSelect
Set within 13 minutes' walk of The Oldest House, the Conch Casa Villa lies in the Duval district of Key West.
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
Apartment
1.9 km from City Centre200 m from Ernest Hemingway House
From   US$ 365 /nightSelect
While staying at the Mermaid'S Retreat you are invited to discover Mel Fisher Maritime Heritage Museum, set approximately a 15-minute walk away, or Mallory Square, which is about a 15-minute walk away.
1.8 km from City Centre200 m from Ernest Hemingway House
From   US$ 1 091 /nightSelect
While staying at the Duval Street Suite With Pool you are invited to discover Mallory Square, set nearly a 15-minute stroll away, or US 1 Mile Marker 0, which is 750 metres away.
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.
  • Private entrance
  • Fitness centre
  • Massage services
800 m from City Centre1000 m from Smathers Beach
From   US$ 651 /nightSelect
  • Private sauna for ultimate relaxation
  • Air-conditioned apartment with sea views
  • On-site tennis and golf facilities
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