Top Holiday rentals in Florida Keys
Find the Top Holiday rentals in Florida Keys – 50+ Quality Options from Leading Providers
1-20 out of 50 holiday rentals
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Lodge
4 adults
1 bedroom
1 bed
From
US$ 147
/night
- Marina with kayak rentals and charters
- Outdoor pool open all year round
- Evening entertainment available onsite
Lodge
4 adults
1 bedroom
2 beds
From
US$ 333
/night
- Private beach with stunning sunsets
- Heated pool surrounded by lush gardens
- Complimentary kayaks and paddleboards available
Holiday home
- Outdoor Pool
- Bar Area
- Lake Views
From
US$ 205
/night
- On-site bar and outdoor dining area
- Pet-friendly accommodations available
- Outdoor swimming pool with lake views
9.4
Perfect11 review10
- Saltwater Pool
- Grilling Stations
- Kayak Rentals
From
US$ 149
/night
- Largest fleet rentals in the Keys
- Newly remodeled cottages and cabins
- Beautiful saltwater pool access
Villa
- Heated Pool
- Private Villas
- Outdoor Dining
From
US$ 709
/night
- Heated outdoor swimming pool
- Fully equipped kitchen in each villa
- Adjacent to Duval Street shopping
Holiday home
- Hot tub
- Cycling
- Patio
From
US$ 270
/night
- Private entrance holiday home
- On-site hot tub for relaxation
- Pet-friendly accommodation
Holiday home
- Tiki Bar
- Peaceful Gardens
- Private Entrance
From
US$ 135
/night
- Private outdoor shower for adventurous guests
- Relaxing atmosphere with tranquil gardens
- Tiki bar serving drinks and cold beer
From
US$ 950
/night
Situated 4.5 km from Marathon Airport, this venue features a private pool.
Apartment
- Private Beach
- Tennis Courts
- Resort Marina
From
US$ 142
/night
- Junior Olympic-size swimming pool
- Private Marina for boating access
- Oceanfront suites with private balconies
Holiday home
From
US$ 564
/night
The Passover Cottage is a good starting point to Key West's sights including Mel Fisher Maritime Heritage Museum, which is less than a 10-minute stroll away.
Villa
- Heated Pool
- Bicycle Rentals
- Outdoor Jacuzzi
From
US$ 561
/night
- Heated outdoor pool open year-round
- Fully-equipped kitchens in apartments
- Bicycle rentals for local exploration
Apartment
From
US$ 470
/night
The Traveler'S Palm is situated in the museum Duval district, 10 minutes' drive from Key West International airport.
Apartment
- Outdoor Pool
- Sun Terrace
- Barbecue Facilities
From
US$ 177
/night
- Shared outdoor pool with waterfall
- Tropical decor in individual rooms
- Bicycle rentals available onsite
From
US$ 763
/night
Nestled in the Duval district, the Duval Street Suite Overlooking Duval With Parking And Pool is within an easy walking distance to Key West Lighthouse and Keeper's Quarters Museum.
Holiday home
From
US$ 325
/night
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.
Apartment
- Private Beach
- Heated Pool
- Tennis Court
From
US$ 223
/night
- Private beach access for guests
- Heated outdoor swimming pool available
- On-site tennis court for activities
Holiday home
- Private Beach
- Outdoor Pool
- Tennis Court
From
US$ 160
/night
- Private beach access
- Year-round outdoor pool
- On-site tennis court
Apartment
- Outdoor pool
- Private entrance
- Fully equipped kitchen
From
US$ 408
/night
- Private entrance to accommodations
- Outdoor swimming pool for relaxation
- Fully equipped kitchen in each unit
Apartment
- Heated pool
- Fitness centre
- Hot tub
From
US$ 122
/night
- Private entrance with accommodation privacy
- Heated outdoor swimming pool available
- On-site fitness centre for workouts
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