Top Vacation homes in Key West

Find the Top Vacation homes in Key West – 10+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-18 out of 18 vacation homes
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Holiday home
8 adults
3 bedrooms
4 beds
MapView on map1.1 mi from City Center200 yd from Duval Street
From   US$ 1 360 /nightSelect
  • Private entrance for added privacy
  • Outdoor swimming pool for relaxation
  • Activities like cycling and fishing
MapView on map3.1 mi from City Center1300 yd from Kayak Kings Key West
From   US$ 463 /nightSelect
  • Heated pool with private entrance
  • Fully equipped kitchen with dishwasher
  • On-site golf and tennis courts
1.4 mi from City Center400 yd from San Carlos Institute Casa Cuba
From   US$ 1 598 /nightSelect
1.9 mi from City Center1200 yd from Kayak Kings Key West
From   US$ 595 /nightSelect
Set 1.1 miles from Sheriff s Animal Farm, this apartment has a fully-fitted kitchen and 2 bathrooms.
8.8
Great13 reviews
  • Heated pool
  • Private balconies
  • Pet-friendly
1.3 mi from City Center400 yd from San Carlos Institute Casa Cuba
From   US$ 709 /nightSelect
  • Heated outdoor swimming pool
  • Fully equipped kitchens in each villa
  • Steps from Duval Street dining
Holiday home
1.4 mi from City Center500 yd from Mallory Square
From   US$ 828 /nightSelect
3.1 mi from City Center1300 yd from Kayak Kings Key West
From   US$ 615 /nightSelect
1500 yd from City Center300 yd from Dog Beach
From   US$ 872 /nightSelect
Holiday home
1.1 mi from City Center300 yd from San Carlos Institute Casa Cuba
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Offering a fully-fitted kitchen complete with oven and a dishwasher, this villa is located close to Nancy Forrester's Secret Garden.
  • Outdoor Pool
  • Cycling Activities
  • Dock Access
800 yd from City Center1100 yd from Key West Cemetery
From   US$ 547 /nightSelect
  • Private entrance for enhanced privacy
  • Outdoor swimming pool for relaxation
  • Sea views from spacious patio
1.1 mi from City Center200 yd from Duval Street
From   US$ 446 /nightSelect
The Casita De Catherine By Avantstay 1 Block To Duval St W Hot Tub Key West is nestled in the Duval district, San Carlos Institute is 0.6 km away.
  • 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$ 236 /nightSelect
  • Close to Southernmost Point
  • Air-conditioned holiday home
  • Pets allowed
Holiday home
1.2 mi from City Center100 yd from Fury Water Adventures Key West
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3.3 mi from City Center1.0 mi from Kayak Kings Key West
From   US$ 2 726 /nightSelect
You can relax by a private pool in the Crestwood House - Private Heated Pool & Parking Key West, located approximately 20 minutes by foot from Safe Harbor.
Holiday home
1.4 mi from City Center500 yd from Mallory Square
From   US$ 711 /nightSelect
Holiday home
1.0 mi from City Center200 yd from Duval Street
From   US$ 1 399 /nightSelect
1.1 mi from City Center200 yd from Fury Water Adventures Key West
From   US$ 1 909 /nightSelect
Located less than merely 150 metres from The Ernest Hemingway Home and Museum, the New Listing Palm Escape- Luxury Home W Pool Key West offers a private pool.