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Featured Vacation Homes in Key West

Casa Cove New Beautiful Tropical Decorated 3 King Suites - Sleeps 8 - Pool
Casa Cove New Beautiful Tropical Decorated 3 King Suites - Sleeps 8 - Pool
Key West, FL
5.0/5 (1 reviews)
At this vacation home, guests have access to a fitness center and barbecue grills.
Starfish - Sunny Townhome in Quiet Truman Annex TWO Blocks From Duval ST
Starfish - Sunny Townhome in Quiet Truman Annex TWO Blocks From Duval ST
Key West, FL
5.0/5 (1 reviews)

I loved Starfish!!! Beautifully decorated and maintained. Perfect location with pool just out the back gate

Reviewed on Aug 13, 2020
Guests staying at this vacation home have access to a garden and barbecue grills.
TIRED OF BEING INSIDE! Ask about our November specials
TIRED OF BEING INSIDE! Ask about our November specials
Key West, FL
4.0/5 (1 reviews)

Bed too hard for my wife Place very tiny especially the bathroom

Reviewed on Oct 14, 2019
This resort is a smoke-free resort.
Real World MTV House---not Just a House Your Own Private Resort
Real World MTV House---not Just a House Your Own Private Resort
Key West, FL
$2,099
Guests of this resort have access to an outdoor pool, a fitness center, and a spa tub. Transportation is made easy with limo/town car service. Other amenities ...
Oversized Oldtown Home for the Whole Family With Private Pool and Dock!
Oversized Oldtown Home for the Whole Family With Private Pool and Dock!
Key West, FL
Guests staying at this vacation home enjoy a spa tub, an outdoor tennis court, and barbecue grills.
A Castle On An Island!! Your Key West Island Retreat!! Sleeps 24
A Castle On An Island!! Your Key West Island Retreat!! Sleeps 24
Key West, FL
$1,599
Guests of this vacation home enjoy features like a spa tub.
Lazy River Pool, Enchanting Garden, Old Town Key West, Free Wifi, Bikes & Parkin
Lazy River Pool, Enchanting Garden, Old Town Key West, Free Wifi, Bikes & Parkin
Key West, FL
Transportation is made easy with limo/town car service.
@@ Steps From Duval 1 Bedroom Townhouse in Great Complex Hidden Secret @@
@@ Steps From Duval 1 Bedroom Townhouse in Great Complex Hidden Secret @@
Key West, FL
At this vacation home, guests have access to an outdoor tennis court.
Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Key West, FL
This vacation home features a spa tub and barbecue grills.
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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.

Hotel Options in Key West

See all 1,803 Properties in Key West
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.