Key West Private Vacation Homes
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Featured Holiday Homes in Key West

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
This holiday home's great location gets high marks from our customers. During your stay, you're just a quick walk from Duval Street. You'll find features such as an outdoor pool and 1 hot tub. Enjoy your stay with amenities like a kitchen and 2.5 bathrooms in the holiday home.
Pool
Hot tub

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
During your stay at this holiday home, you're just a quick walk from Duval Street. Enjoy features like concierge services. Free WiFi and a private pool are available in the holiday home.
Pool
Kitchen

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
During your stay at this holiday home, you're just a quick walk from Key West Firehouse Museum. The holiday home includes amenities such as free WiFi and a kitchen.
Kitchen
Free WiFi

Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio
Our customers tell us they can't get enough of this holiday home's great location. During your stay, you're just a quick walk from Key West Firehouse Museum. The holiday home includes amenities such as a kitchen and a patio.
Kitchen
Air conditioning

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
During your stay at this holiday home, you'll be within walking distance of Stock Island Yacht Club & Marina. Features include 1 hot tub and concierge services. Free WiFi and a kitchen are available in the holiday home.
Hot tub
Kitchen

Captain's Daughter: Oversized home for the whole family w/private pool & dock
This holiday home's great location gets high marks from our customers. During your stay, you're just a quick walk from The Unitarian Universalist Fellowship of Key West. You'll find features such as concierge services. The holiday home offers free WiFi and a private pool.
Pool
Kitchen

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
During your stay at this holiday home, you're just a quick walk from Duval Street. Enjoy features like concierge services. Free WiFi and a private pool are available in the holiday home.
Pool
Kitchen

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you're just a quick walk from Duval Street. You'll find features such as concierge services. Enjoy your stay with amenities like free WiFi and a private pool in the holiday home.
Pool
Kitchen

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
During your stay at this holiday home, you're just a quick walk from Duval Street. The holiday home includes amenities such as free WiFi and a kitchen.
Pool
Kitchen

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you're just a quick walk from Duval Street. Features include concierge services. The holiday home offers free WiFi and a private pool.
Pool
Kitchen

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you're just a quick walk from Duval Street. You'll find features such as concierge services. Free WiFi and a private pool are available in the holiday home.
Pool
Kitchen

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
During your stay at this holiday home, you're just a quick walk from Duval Street. Features include concierge services. Free WiFi and a kitchen are available in the holiday home.
Pool
Kitchen

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
During your stay at this holiday home, you'll be within walking distance of Key West Tropical Forest and Botanical Garden. Enjoy features like a gym and concierge services. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
Kitchen
Washer

Perfect Location, Private Heated Pool & Pristine Luxury Home!
This holiday home's great location gets high marks from our customers. During your stay, you're just a quick walk from Duval Street. Features include an outdoor pool and concierge services. The holiday home includes amenities such as free WiFi and a private pool.
Pool
Kitchen

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you're just a quick walk from Duval Street. Concierge services are available. The holiday home includes amenities such as free WiFi and a private pool.
Pool
Kitchen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Key West Holiday Homes essential information
Accommodation | 1072 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!, EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!, Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach, Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio , ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!, Captain's Daughter: Oversized home for the whole family w/private pool & dock, BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!, SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location, LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!, SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!, NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool, OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!, Perfect Location, Private Heated Pool & Pristine Luxury Home!, A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool! |
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