Key West Vacation Homes

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Featured Vacation Homes in Key West

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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.

Hotel Options in Key West

    Blue Flamingo Resort Key West

    Blue Flamingo Resort Key West

    3820 North Roosevelt Boulevard Key West FL
    $195 nightly
    The price is $219 total per night from May 31 to Jun 1
    $219 total
    May 31 - Jun 1
    Total with taxes and fees
    8.4/10 Very Good! (2,160 reviews)
    Beachside Resort & Residences

    Beachside Resort & Residences

    3841 N Roosevelt Blvd Key West FL
    $251 nightly
    The price is $283 total per night from May 11 to May 12
    $283 total
    May 11 - May 12
    Total with taxes and fees
    8.6/10 Excellent! (2,191 reviews)
    Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    2001 South Roosevelt Boulevard Key West FL
    $268 nightly
    The price is $302 total per night from May 26 to May 27
    $302 total
    May 26 - May 27
    Total with taxes and fees
    8.8/10 Excellent! (1,797 reviews)

Key West Vacation Homes

Book vacation homes in Key West
Next time you take a group getaway top Key West, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Key West vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Key West vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Key West; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Key West rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Key West is sure to be a winner.

Key West Vacation Homes essential information

Accommodation
890 Vacation Homes
Lowest Price
$219
Highest Price
$2,477
Popular accommodation
Villa Déjà vu Key West - 4BR Private Villa in Old Town Key West with Heated Pool sleeps 10, BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL, CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!, EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!, A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!, PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!, MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!, Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location, Conch style home in Oldtown with private pool AND dock!

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