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

Key West Vacation Rentals

Browse 5,832 available vacation homes and compared across 13 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

Accommodation Key West
Rental with pool, yard & terrace | Next to Duval Street
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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
Fully equipped wonderful vacation home with barbeque, patio & yard | Next to West Martello Tower | Nature view | Beach nearby | Good for workation
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House Key West
2027 calendar is now available! Old Town historic home Lagoon Pool 3BR ️ ️ ️ ️ ️
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House Key West
Fully equipped charming vacation home with barbecue, patio & garden
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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
House with private pool, barbeque & patio | Nature view
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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
CASA OLIVIANA @ SOLARES HILL Grand Home & Pool LAST KEY SERVICES...
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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
Fully equipped house with yard, terrace & hot tub | Near Duval Street | City view
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House Key West
Fully equipped vacation home with terrace, hot tub & barbecue
Book now

Top 15 most Recommended Vacation Rentals in Key West

Discover your ideal Key West vacation rental with real-time comparisons of 5,832 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Key West
House ∙ 10 guests ∙ 3 bedrooms

Wonderful vacation home with BBQ & patio | Dogs allowed

Key West, Monroe County, Florida, United States
This spacious houseboat in Key West accommodates 10 guests and features a fully equipped kitchen for your convenience.
from $238
per night
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House Key West
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with grill, private pool & garden | Close to Southernmost Point | City view

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 4 guests and features a private pool for relaxation and enjoyment.
from $325
per night
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House Key West
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with barbeque, garden & private pool | Nature view

Key West, Monroe County, Florida, United States
This house rental in Key West accommodates 6 guests and features a private pool for a relaxing getaway.
from $233
per night
(12)
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House Key West
House ∙ 8 guests ∙ 4 bedrooms

House with patio, pool & garden | Good for workation

Key West, Monroe County, Florida, United States
This spacious house rental in Stock Island accommodates 8 guests and features a relaxing pool for your enjoyment.
from $379
per night
(163)
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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 $240
per night
(18)
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House Key West
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped lovely house with grill, pool & patio | Close to Key West Tropical Forest & Botanical Garden | Pool view

Key West, Monroe County, Florida, United States
This house rental in Stock Island accommodates 4 guests and features a refreshing pool for relaxation and enjoyment.
from $125
per night
(3)
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House Key West
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio & barbecue | Next to Southernmost Point

Key West, Monroe County, Florida, United States
Charming house rental in Bahama Village, accommodating 4 guests, featuring beach access for a perfect getaway.
from $189
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 $515
per night
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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 $719
per night
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