Top Holiday rentals in Florida Keys

Find the Top Holiday rentals in Florida Keys – 50+ Quality Options from Leading Providers

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22 Guests, 1 Room
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21-40 out of 50 holiday rentals
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Holiday home
8 adults
3 bedrooms
3 beds
From   US$ 1 042 /nightSelect
This villa in the Duval district is composed of 3 bedrooms, a kitchen and 2 bathrooms.
6 adults
2 bedrooms
3 beds
From   US$ 491 /nightSelect
  • Outdoor swimming pool and hot tub
  • Two separate bedrooms and bathrooms
  • Private entrance for added privacy
Holiday home
  • Outdoor dining
  • Private entrance
  • Cable TV
From   US$ 210 /nightSelect
  • Cycling and fishing activities available
  • Private outdoor dining area for guests
  • Air-conditioned rooms with kitchen options
  • Private beach
  • Outdoor pools
  • Kids' pool
From   US$ 315 /nightSelect
  • Private beach access
  • Pool with ocean views
  • Children's play area
  • Private Entrance
  • Coffee Machine
  • Fishing Activities
From   US$ 64 /nightSelect
  • Private entrance for guest convenience
  • Close to popular attractions and beaches
  • Air-conditioned units with seating areas
Holiday home
From   US$ 3 054 /nightSelect
Offering a kitchen complete with a dishwasher, refrigerators and an oven, this villa is located close to American Outdoors.
Villa
  • Air conditioning
  • Fully equipped kitchen
  • Private entrance
From   US$ 188 /nightSelect
  • Scenic sea view balcony
  • Outdoor dining area
  • Children's playground area
  • Snack bar
  • Picnic area
  • Balanced kitchens
From   US$ 250 /nightSelect
  • Outdoor dining area with garden views
  • On-site barbecue facilities available
  • Picnic area for outdoor activities
  • City Views
  • Fully Equipped Kitchen
  • Private Entrance
From   US$ 627 /nightSelect
  • Private entrance with city views
  • Close to iconic attractions and beaches
  • Equipped kitchen with dishwasher
  • Sea views
  • Tennis court
  • Private parking
From   US$ 404 /nightSelect
  • Private entrance and sea views
  • On-site tennis court available
  • Equipped kitchen for self-catering
Holiday home
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
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
From   US$ 570 /nightSelect
Conch Key, Florida is approximately 25 minutes' walk from the Restful Retreat Villa Duck Key, while Keys Cable Park is 3.3 km away.
Holiday home
  • Heated pool
  • Private entrance
  • Outdoor patio
From   US$ 333 /nightSelect
  • Outdoor heated swimming pool
  • Close to Ernest Hemingway Home
  • Private entrance for added privacy
Apartment
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.
Holiday home
From   US$ 139 /nightSelect
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.
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
From   US$ 903 /nightSelect
  • Outdoor swimming pool for relaxation
  • Full kitchen with modern appliances
  • Pet-friendly private holiday home
  • Private entrance
  • Fitness centre
  • Massage services
From   US$ 696 /nightSelect
  • Private sauna for ultimate relaxation
  • Air-conditioned apartment with sea views
  • On-site tennis and golf facilities