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Key West Holiday Rentals

81 Key West Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Key West, Florida Keys, Florida, United States.
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Listings 1 - 25 of 81
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a...
Rates
$340 - $703 night
$2205 - $4720 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dini...
Rates
$265 - $486 night
$1575 - $3118 week


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3 bedroom Vacation Rental Home in Key West - Lake View
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: SUNSET LAKE -- Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping, this 3-bedro...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: ATLANTIC BLUES - Stylish Conch cottage with hardwood floors, glass tiles, granite countertops and d├ęcor that is playful and soothing. Kitchen...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: BOGEY'S RETREAT: Ideal for a golfer, it is located at Key West Golf Club. 2 pools nearby. $50 security deposit for Association gym card us...
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: KEY WEST FOUND: 2 bedroom, 2.5 bath townhome in the historic brick Foundry building within the Truman Annex. Decorated in a whimsical Key West st...
Rates
$1650 - $3806 week


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with pr...
Rates
$625 - $1298 night
$4165 - $8374 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condo. Enjoy the ocean breezes while unwinding on your private balcony in this tast...
Rates
$300 - $494 night
$1800 - $3250 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: KEY WEST CROWN JEWEL: 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space. WIFI, flat-screen plasma television with Bo...
Rates
$345 - $531 night
$2145 - $3369 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of O...
Rates
$265 - $486 night
$1575 - $3118 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A PLACE IN PARADISE - Experience Key West living in this 2 bedroom 2.5 bath Conch-Style home in Truman Annex. This home features a fully equipp...
Rates
$1625 - $3989 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: 4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downt...
Rates
$220 - $400 night
$1325 - $2594 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: A SUITE PARADISE - A tropical hideaway tucked in a secluded Key West neighborhood minutes from Duval Street entertainment. 2 bedroom 2 bath priva...
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-bedroom 2.5 bath home has it all! Living room h...
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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks from Duval Street. Completely renovated, this l...
Rates
$160 - $355 night
$935 - $2284 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: SUNNY VIEW: Adorable, affordable, and a great location! Located in Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest and...
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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: BOATER'S BEACH HAVEN: Located midtown on Florida Bay. Take advantage of the private boat dock; bring your own boat or rent one in Key West. Ol...
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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: EASY LIVIN' : Private home with pool in Truman Annex, a gated community in historic Old Town, in walking distance of anything you'll want to do ...
Rates
$4000 - $9200 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: ARTIST GARDEN : 2 bedroom 2.5 bath located in the prestigious Admirals Lane neighborhood of Truman Annex. Open floor plan on the main level with...
Rates
$1890 - $4002 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: PAPAYA PLACE: 2 bedroom 2 bath condo at 1800 Atlantic Blvd. with garden view overlooking the nature preserve. Master bedroom with new king bed...
Rates
$220 - $400 night
$1325 - $2594 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: EGRET COTTAGE -- An idyllic 1 bedroom cottage that is tucked away in a tropical oasis, peaceful and serene yet located in one of the most ideal nei...
Rates
$195 - $384 night
$1100 - $2429 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: TRES GATOS: Spend a month (or two) in one of Key West's most revered neighborhoods and live like a local in this sweet 2-bedroom Conch cottage. A...
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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: LAVENDER JUNGLE: 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex. Renovated kitchen and upgraded bathroom. Large brick patio...
Rates
$1235 - $2828 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated...
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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand. 60" Smart TV and surround sound in living room; Dade County pine walls...
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