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Key West vacation rentals

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Holiday homes

1308 properties found in Key West

  • Trout Key

    Trout Key

    Marathon, United States
    The 1-bedroom Trout Key Villa is located at a 400-metre distance from Marathon Cinema and features a swimming pool and a patio for a relaxing stay. Located relatively near Pretty Joe Rock, this…
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    US$ 383 price for 1 night
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  • Casa Feliz- Private Beachfront Oasis, Heated Pool, Movie Room & More!

    Casa Feliz- Private Beachfront Oasis, Heated Pool, Movie Room & More!

    58652 Overseas Highway
    The 4-bedroom Casa Feliz- Private Beachfront Oasis, Heated Pool, Movie Room & More! Marathon offers proximity to such city sites as Grassy Key Island, located approximately a 10-minute walk away.
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  • Hellenga Haven

    Hellenga Haven

    1700 Hellenga Dr
    Offering a location around a 5-minute drive from No Name Key, the 3-bedroom Hellenga Haven Villa gives access to various tourist spots in the area.
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  • World'S End

    World'S End

    109 Front Street #113
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  • Southernmost View -Pool & Water Views

    Southernmost View -Pool & Water Views

    Downtown Key West
    The 4-bedroom Southernmost View -Pool & Water Views Villa features a patio with views of the sea as well as a swimming pool. Featuring a car park, this accommodation is located merely 1.6 km from…
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  • Southernmost Hospitality V By Last Key Realty

    Southernmost Hospitality V By Last Key Realty

    Downtown Key West
    Located merely 13 minutes' walk from Dog Beach, the 6-bedroom Southernmost Hospitality V By Last Key Realty Villa provides access to a swimming pool. Staying at the Key West villa, right next to…
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  • Reel Deal - Waterfront Pool Home, 76' Dock

    Reel Deal - Waterfront Pool Home, 76' Dock

    233 112Th Street Ocean
    Reel Deal - Waterfront Pool Home, 76' Dock Marathon is located a 19-minute walk from Oceanfront Park and provides a private swimming pool, ensuring a relaxing stay.
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    US$ 465 price for 1 night
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  • Spacious 52' Sailboat | 6 Cabins | Dockside Escape

    Spacious 52' Sailboat | 6 Cabins | Dockside Escape

    7005 Shrimp Road
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  • Margaret Street Retreat

    Margaret Street Retreat

    Downtown Key West
    Located merely 6 minutes' walk from 7 Artists & Friends Gallery, Margaret Street Retreat Villa Key West offers quick access to various city attractions in the vicinity.
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    US$ 615 price for 1 night
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  • Old Town Getaway

    Old Town Getaway

    Downtown Key West
    Located about 25 minutes' walk from Higgs Beach Dog Park, the 1-bedroom Old Town Getaway Villa Key West provides access to various tourist attractions in the vicinity.
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  • Tranquility In Paradise - Sugarloaf - 17 Miles To Key West

    Tranquility In Paradise - Sugarloaf - 17 Miles To Key West

    17084 Green Turtle Lane West
    The 3-bedroom Tranquility In Paradise - Sugarloaf - 17 Miles To Key West Villa is located at a distance of 3.6 km from Jumping Bridge and provides a Jacuzzi. This accommodation features opportunities…
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  • Beachside Retreat W/ Pool, Boat Ramp Dock For Rent

    Beachside Retreat W/ Pool, Boat Ramp Dock For Rent

    Lot 155, 101551 Overseas Highway
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  • A Windsong Delight

    A Windsong Delight

    Downtown Key West
    Situated in the Downtown Key West district, the 3-bedroom A Windsong Delight Villa offers guests to indulge in windsurfing, snorkelling, and canoeing, or unwind by a private pool. Featuring access to…
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  • Crystal Waters - 2Br 3Ba Private Villa

    Crystal Waters - 2Br 3Ba Private Villa

    5089 Sunset Village Drive
    Located merely a 5-minute walk from Hawks Cay Boulevard, Crystal Waters Villa Duck Key offers a sunbathing terrace with a view over the street. Providing guests with Wi-Fi and parking, the 3-bedroom…
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    US$ 569 price for 1 night
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  • Serenity By Avantstay Guest House In Old Town W Shared Pool Month Long Stays Only

    Serenity By Avantstay Guest House In Old Town W Shared Pool Month Long Stays Only

    Downtown Key West
    Featuring a swimming pool, the 1-bedroom Serenity By Avantstay Guest House In Old Town W Shared Pool Month Long Stays Only villa is nestled in the Downtown Key West district of Key West and offers…
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    US$ 204 price for 1 night
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  • Louisas Hideaway

    Louisas Hideaway

    Downtown Key West
    Situated in the Duval district, at a 200-metre distance from The Ernest Hemingway Home and Museum, the 3-bedroom Louisas Hideaway Villa comes with a heated pool for guests to unwind. Guests can enjoy…
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  • A Gulfview Paradise

    A Gulfview Paradise

    2635 Gulfview Drive
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  • Luxury Key Largo Home With Guest House And Pool!

    Luxury Key Largo Home With Guest House And Pool!

    45 Mutiny Pl
    Located within convenient reach of Island Dolphin Care, the 4-bedroom Luxury Key Largo Home With Guest House And Pool! provides an outdoor pool as well as canoeing to diversify guests' leisure.
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  • Palms 309

    Palms 309

    79901 Overseas Hwy.
    The 2-bedroom Palms 309 Villa Islamorada is located within a 4-km distance of Lobster Trap Art Gift Shop and Gallery and provides a hot tub. This Islamorada holiday home features opportunities for…
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  • Keys Wade New 1B 2Bath

    Keys Wade New 1B 2Bath

    10877 Overseas Highway
    Located 10 minutes on foot from Eaa Air Museum, the 2-bedroom Keys Wade New 1B 2Bath Villa gives access to various tourist sites in the vicinity.
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