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Key West vacation rentals

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Holiday homes

658 properties found in Key West

  • Keys Please

    Keys Please

    1408 Petronia St.
    Offering garden views, the 3-bedroom Keys Please Villa Key West is situated a mere 9 minutes' walk from the 19-acre Key West Cemetery.
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  • Reynolds Retreat

    Reynolds Retreat

    Downtown Key West
    Staying at Reynolds Retreat Villa Key West, guests can easily reach Key West First Legal Rum Distillery, located approximately a 10-minute drive away.
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  • Ashe Street Serenade

    Ashe Street Serenade

    Downtown Key West
    Situated in the Downtown Key West district, within a 900-metre distance of Historic Charter Boat Row, Ashe Street Serenade Key West villa comes with a private pool for guests to unwind.
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    US$ 390 price for 1 night
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  • Flagler Station

    Flagler Station

    1430 Flagler Ave.
    The 2-bedroom Flagler Station Villa Key West is located just 500 metres from Higgs Beach Dog Park and features a private swimming pool as well as a patio for guests' pleasure.
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    US$ 290 price for 1 night
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  • Sweet'S Spot

    Sweet'S Spot

    109 Front Street #309
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  • Petes Cottages

    Petes Cottages

    Downtown Key West
    Nestled a 17-minute walk from Ripley's Believe It or Not Museum, Petes Cottages Key West entices guests to explore various tourist destinations nearby.
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    US$ 1055 price for 1 night
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  • Royal Palm Studio At Travelers Palm Inn Key West

    Royal Palm Studio At Travelers Palm Inn Key West

    Downtown Key West
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  • Casa De Rosalie By Avantstay Great Location W Pool Bbq Outdoor Dining Month Long Stays Only

    Casa De Rosalie By Avantstay Great Location W Pool Bbq Outdoor Dining Month Long Stays Only

    1419 Truman Avenue
    Situated in a historic district, about a 25-minute walk from West Martello Tower, the welcoming Casa De Rosalie By Avantstay Great Location W Pool Bbq Outdoor Dining Month Long Stays Only Key West…
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  • The Joyrise House At Solaire Lunara Bay

    The Joyrise House At Solaire Lunara Bay

    12 Andrea Lane

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    US$ 3676 price for 1 night
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  • A Fish Bowl

    A Fish Bowl

    620 Thomas Street #189
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  • Seafarer'S Refuge

    Seafarer'S Refuge

    719 Eisenhower Drive #2, #2
    Situated within a 200-metre distance of Wreckers Sloop Mary, the 3-bedroom Seafarer'S Refuge Villa offers guests to take advantage of barbecue and a golf course. Featuring a heated pool, this…
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    US$ 1483 price for 1 night
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  • New The Altair House - Fire Pit Pool & Hot Tub

    New The Altair House - Fire Pit Pool & Hot Tub

    Mangrove Lane 13
    Situated around 4 km from Fort East Martello Museum, the 7-bedroom New The Altair House - Fire Pit Pool & Hot Tub Villa Key West invites guests to relax at a patio.
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    US$ 1549 price for 1 night
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  • Casa Oliviana By Last Key Realty

    Casa Oliviana By Last Key Realty

    Downtown Key West
    The 4-bedroom Casa Oliviana By Last Key Realty Key West offers quick access to such city attractions as Southernmost Point of the Continental US, located just 6 minutes' walk away.
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  • Blanco Luxury Villa

    Blanco Luxury Villa

    Downtown Key West
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  • It'S A Salt Life After All

    It'S A Salt Life After All

    159 Golf Club Drive
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  • Sand Crab Cabana Weekly Rental!

    Sand Crab Cabana Weekly Rental!

    620 Thomas Street, #269
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  • A Sunset Celebration

    A Sunset Celebration

    95 Golf Club Drive
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  • Booty Caye

    Booty Caye

    73 Golf Club Drive
    Located nearly a 15-minute ride from the secluded pocket Dog Beach, the 1-bedroom Booty Caye Villa Key West provides access to a swimming pool. Featuring a terrace, the Key West holiday home is…
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    US$ 179 price for 1 night
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  • Casa Blanca

    Casa Blanca

    Downtown Key West
    Located merely 8 minutes' walk from Higgs Beach, the 3-bedroom Casa Blanca Villa offers a heated swimming pool for guests to relax by. The villa features opportunities for windsurfing, snorkelling…
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  • Captiva At Azul Mansion Key West

    Captiva At Azul Mansion Key West

    Downtown Key West
    At Captiva At Azul Mansion Key West villa, guests can enjoy windsurfing, snorkelling, and fisheries as well as a location around a 5-minute walk from the historic Saint Mary Star of the Sea Church.
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