Top Vacation homes in Key West

Find the Top Vacation homes 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 22 vacation homes
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6 adults
3 bedrooms
3 beds
MapView on map1.3 mi from City Center400 yd from San Carlos Institute Casa Cuba
From   US$ 246 /nightSelect
  • Heated outdoor swimming pool
  • Fully equipped kitchens in each villa
  • Steps from Duval Street dining
Holiday home
6 adults
2 bedrooms
4 beds
MapView on map800 yd from City Center1000 yd from Smathers Beach
From   US$ 408 /nightSelect
  • Private entrance to all units
  • Outdoor swimming pool available
  • Staff assist with cycling activities
  • Heated Pool
  • Private Entrance
  • Fitness Centre
3.1 mi from City Center1300 yd from Kayak Kings Key West
From   US$ 886 /nightSelect
  • Heated pool with private entrance
  • Fully equipped kitchen with dishwasher
  • On-site golf and tennis courts
  • Private Entrance
  • Coffee Machine
  • Air Conditioning
1.2 mi from City Center200 yd from San Carlos Institute Casa Cuba
From   US$ 64 /nightSelect
  • Private entrance for guest convenience
  • Well-equipped kitchen utensils provided
  • Proximity to popular beaches and attractions
Holiday home
  • Outdoor pool
  • Private entrance
  • Full kitchen
1.1 mi from City Center200 yd from Duval Street
From   US$ 947 /nightSelect
  • Private entrance for added privacy
  • Outdoor swimming pool for relaxation
  • Activities like cycling and fishing
Holiday home
  • Private Pool
  • Full Kitchen
  • Outdoor Dining
500 yd from City Center1100 yd from Dog Beach
From   US$ 290 /nightSelect
  • Private pool and outdoor dining area
  • Spacious home with three bedrooms
  • Activities like cycling and fishing
1.1 mi from City Center200 yd from Duval Street
From   US$ 446 /nightSelect
Located right in the centre of Key West, the Casita De Catherine By Avantstay 1 Block To Duval St W Hot Tub offers fast access to USCGC Ingham Maritime Museum, a mere 10 minutes' stroll away.
Holiday home
800 yd from City Center900 yd from Dog Beach
From   US$ 258 /nightSelect
Set within walking distance of West Martello Tower, this villa includes 3 bedrooms and a kitchen for guests' convenience.
  • Outdoor Pool
  • Fitness Centre
  • Patio
1.9 mi from City Center1200 yd from Kayak Kings Key West
From   US$ 282 /nightSelect
  • Outdoor pool with private entrance
  • Well-equipped kitchen with dishwasher
  • Close to popular cycling trails
  • Outdoor pool
  • EV charger
  • Garden area
1.1 mi from City Center200 yd from Ernest Hemingway House
From   US$ 763 /nightSelect
  • Outdoor pool for relaxation
  • On-site parking with EV charger
  • Centrally located near attractions
Holiday home
  • Fully equipped kitchenette
  • Living room
  • Non-smoking accommodation
1.1 mi from City Center200 yd from Duval Street
From   US$ 380 /nightSelect
  • Close to Southernmost Point
  • Air-conditioned holiday home
  • Pets allowed
  • Outdoor Pool
  • Cycling Activities
  • Dock Access
700 yd from City Center1100 yd from Key West Cemetery
From   US$ 808 /nightSelect
  • Private entrance for enhanced privacy
  • Outdoor swimming pool for relaxation
  • Sea views from spacious patio
  • Outdoor pool
  • Hot tub
  • Bike rentals
1.1 mi from City Center100 yd from Fury Water Adventures Key West
From   US$ 561 /nightSelect
  • Heated outdoor swimming pool
  • Fully-equipped kitchen in apartments
  • Bicycle rentals for local exploration
  • Private Entrance
  • Fitness Centre
  • Outdoor Pool
3.6 mi from City Center
From   US$ 325 /nightSelect
  • Outdoor swimming pool with city views
  • Private entrance for enhanced privacy
  • Access to fitness centre and cycling
Holiday home
  • Hot tub
  • Patio
  • Cycling
1.1 mi from City Center300 yd from Duval Street
From   US$ 270 /nightSelect
  • Private hot tub for ultimate relaxation
  • Air-conditioned accommodation with patio
  • Access to cycling and fishing activities
Holiday home
  • Hot tub
  • Private entrance
  • Fully equipped kitchen
1.1 mi from City Center100 yd from Ernest Hemingway House
From   US$ 879 /nightSelect
  • Private entrance for added privacy
  • Hot tub access for relaxation
  • Pet-friendly accommodations available
Holiday home
  • Hot Tub
  • Kitchen
  • Patio
1.0 mi from City Center300 yd from Ernest Hemingway House
From   US$ 312 /nightSelect
  • Private entrance for added privacy
  • Hot tub available on-site
  • Pets allowed for furry companions
Holiday home
  • Hot tub
  • Air conditioning
  • Private entrance
1.1 mi from City Center200 yd from Ernest Hemingway House
From   US$ 850 /nightSelect
  • Private hot tub for relaxation
  • Air-conditioned rooms with private entrance
  • Fully equipped kitchen with utensils
Holiday home
  • Heated pool
  • Outdoor patio
  • Fully equipped kitchen
1.2 mi from City Center200 yd from Fury Water Adventures Key West
From   US$ 333 /nightSelect
  • Heated outdoor swimming pool
  • Steps from Ernest Hemingway Home
  • Private entrance for added privacy
  • Outdoor Pool
  • Private Parking
  • Air Conditioning
1700 yd from City Center400 yd from Duval Street
From   US$ 903 /nightSelect
  • Outdoor swimming pool for relaxation
  • Fully equipped kitchen for convenience
  • Patio for outdoor dining experience
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