Key West Vacation Rentals - HolidayHomes base64Hash Key West Vacation Rentals - HolidayHomes

Key West Vacation Rentals

Browse 5,615 available vacation homes and compared across 15 trusted partners

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Top-Rated Vacation rentals in Key West

Book the highest-rated Key West vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Key West
Fully equipped charming house with BBQ, jacuzzi & terrace | Nature view | Perfect for remote work | Pets allowed
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House Key West
Vacation home with hot tub, private pool & patio | Next to West Martello Tower | City view
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House Key West
Fully equipped charming vacation home with barbecue, patio & garden
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House Key West
Stone Throw Famous Duval Street Location-No Contact Check-In
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House Key West
LARGE PRIVATE HEATED POOL and PATIO1/3 Mile from Beach
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Condo Key West
Charming 2 Bdrm Oceanfront Oasis Key West Beach access Old Town Bike ride.
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House Key West
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
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House Key West
Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
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House Key West
Welcome To Poseidon's Paradise Midtown Home & Incredible Pool 28 Nights Min
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House Key West
House with patio, garden & private pool | Next to Southernmost Point | Nature view
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House Key West
Fully equipped spacious house with garden, private pool & BBQ | Nature view | Good for workation | Pets are welcome
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House Key West
Children-friendly pleasant vacation home with garden, grill & jacuzzi | Next to West Martello Tower | Next to the beach | Pet-friendly
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Villa Key West
Villa 3 Bdrms/3 baths/close to everything/off st prking/Old Town/15% off July
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Cabin Key West
Cottage with private pool & BBQ | Near West Martello Tower | Nature view
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House Key West
Child-friendly vacation home with yard, private pool & grill | City view | Pets allowed
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Top 15 most Recommended Vacation Rentals in Key West

Discover your ideal Key West vacation rental with real-time comparisons of 5,615 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Key West
House ∙ 16 guests ∙ 6 bedrooms

Fully equipped vacation home with barbecue, garden & private pool | Near Duval Street | Nature view | 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 ultimate relaxation.
from $909
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool, BBQ & garden

Key West, Monroe County, Florida, United States
Spacious house rental in Key Haven for 8 guests featuring a private pool and ample outdoor space for relaxation.
from $449
per night
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House Key West
House ∙ 12 guests ∙ 6 bedrooms

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

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 12 guests and features a private pool for a relaxing getaway.
from $330
per night
View deal
House Key West
House ∙ 8 guests ∙ 4 bedrooms

House with grill, garden & private pool | Close to West Martello Tower | Good for workation

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $246
per night
(2)
View deal
House Key West
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped vacation home with private pool, terrace & garden | Near Southernmost Point | Perfect for remote work | Pet-friendly

Key West, Monroe County, Florida, United States
This Key West house rental accommodates 8 guests and features a private pool for a relaxing getaway.
from $288
per night
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House Key West
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with private pool, garden & patio | Close to Mallory Square | City view

Key West, Monroe County, Florida, United States
Charming house rental in Key West for 6 guests featuring a private pool and a fully equipped kitchen for a perfect getaway.
from $247
per night
(18)
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House Key West
House ∙ 5 guests ∙ 3 bedrooms

Fully equipped vacation home with terrace, grill & private pool | City view | Pet-friendly

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 5 guests and features a private pool for a relaxing getaway.
from $483
per night
(7)
View deal
House Key West
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with pool, terrace & barbecue | Close to Duval Street

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 fun.
from $394
per night
(1)
View deal
House Key West
House ∙ 6 guests ∙ 3 bedrooms

House with BBQ

Key West, Monroe County, Florida, United States
Charming house rental in Key West accommodating 6 guests, featuring a spacious balcony for relaxation and stunning views.
from $268
per night
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