Holiday lettings & accommodation in Florida Keys - HolidayHomes base64Hash Holiday lettings & accommodation in Florida Keys - HolidayHomes

Holiday lettings & accommodation in Florida Keys

Find 14,466 available offers from 32 partners

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Top-Rated Lettings and Properties in Florida Keys

Book Holiday Letting Offers with the Highest User Rating

House Islamorada
The Reef House, Waterfront, Oceanside, 70' Dock, Heated Pool and Spa Home
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House Cudjoe Key
House with 4 rooms for 8 persons
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House Key West
House with terrace, garden & private pool | Close to Duval Street | City view
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House Big Pine Key
Fully equipped holiday home with BBQ | Pets allowed
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House Marathon
Children-friendly holiday home with heated pool, barbeque & terrace | Pets allowed
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House Key Largo
Holiday home with garden, terrace & heated pool | Nature view
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House Marathon
Waterfront Private Home-7 BR, 6 Full BA, Pool, 80' Dock, Parking, Screened Porch
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House Islamorada
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
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House Marathon
House with terrace, barbecue & pool | Nature view
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House Islamorada
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
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House Marathon
2 Incredible Waterfront Homes - One Low Price!
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House Marathon
House with barbeque, terrace & private pool
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House Islamorada
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
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House Islamorada
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
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House Cudjoe Key
PARADISE 3 MINUTES TO OPEN WATER-60FT DOCK-WIDE CANALRESERVE AREA-CUDJOE KEY
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Top 15 Recommended holiday lettings in Florida Keys

Find your perfect vacation rental in Florida Keys from just £89 per night!

House Key West
House ∙ 12 guests ∙ 6 bedrooms

House with garden, BBQ & private pool | Next to West Martello Tower

Key West, Monroe County, Florida, United States
This spacious house rental in Key West accommodates 12 guests and features a private pool for a relaxing stay.
from £228
per night
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House Islamorada
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, garden & barbeque | Nature view | Good for workation

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 8 guests and features a lovely garden for relaxation.
from £439
per night
(1)
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House Islamorada
House ∙ 10 guests ∙ 5 bedrooms

House with barbeque & terrace | Perfect for remote work

Islamorada, Monroe County, Florida, United States
This spacious house rental in Islamorada accommodates 10 guests and features a family-friendly atmosphere with waterside access.
from £302
per night
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House Big Pine Key
House ∙ 8 guests ∙ 3 bedrooms

House with 3 rooms for 8 persons

Big Pine Key, Monroe County, Florida, United States
This spacious house rental in Big Pine Key accommodates 8 guests and features beach access for a perfect seaside getaway.
from £219
per night
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House Key West
House ∙ 16 guests ∙ 6 bedrooms

Fully equipped holiday home with barbecue, garden & private pool | Near Duval Street | Perfect for remote work | Pet-friendly

Key West, Monroe County, Florida, United States
This spacious house rental in Key West accommodates 16 guests and features a private pool for relaxation and enjoyment.
from £779
per night
View deal
House Marathon
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped holiday home with barbecue, terrace & private pool | Pets are welcome

Marathon, Monroe County, Florida, United States
This house rental in Marathon accommodates six guests and features a private pool for a relaxing stay.
from £209
per night
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House Cudjoe Key
House ∙ 4 guests ∙ 2 bedrooms

House with pool

Cudjoe Key, Monroe County, Florida, United States
This charming house rental in Cudjoe Key accommodates four guests and features a refreshing pool for a relaxing stay.
from £185
per night
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House Little Torch Key
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with BBQ, garden & private pool | Good for workation

Little Torch Key, Monroe County, Florida, United States
This house rental in Little Torch Key accommodates 6 guests and features a private pool for a relaxing stay.
from £314
per night
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House Key West
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque, garden & private pool | Close to West Martello Tower | Good for workation

Key West, Monroe County, Florida, United States
This spacious house rental in Key West accommodates 8 guests and features a private pool for relaxation and enjoyment.
from £199
per night
(2)
View deal

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