Beginning of main content

Compare Key West Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Key West

Price for 1 night 2 adults*

Old Town Garden Villas
Old Town Garden Villas
3.5 out of 5.0 921 Center St, Key West, FL
$178

Per night/room

Dec 1 - Dec 2

Old Town Garden Villas features free WiFi in public areas and a garden. Staff members can answer questions about accommodations, and also provide front-desk ...
Secret Villa I @ Old Town With Private Pool, Close to Duval!
Secret Villa I @ Old Town With Private Pool, Close to Duval!
Key West, FL
Guests staying at this villa enjoy features like a water park, an outdoor pool, and a garden. Helpful staff is there to provide concierge services, as well as ...
Grand Dame Key West- The Watson House
Grand Dame Key West- The Watson House
Key West, FL
Guests staying at this villa enjoy a water park, barbecue grills, and a garden.
Duval Penthouse
Duval Penthouse
4.0 out of 5.0 519 Duval Street, # 201, Key West, FL
This villa offers an outdoor pool, a rooftop terrace, and free WiFi in public areas. If you plan to drive, free parking is available. Additional amenities include ...
Villa Déjà vu Key West
Villa Déjà vu Key West
Key West, FL
This villa features a water park and a garden.
Shark Key Chateau Apartment 5
Shark Key Chateau Apartment 5
4.0 out of 5.0 79 Cannon Royal Drive, Key West, FL
Guests of this villa have access to free WiFi in public areas. Friendly staff can provide front-desk service during limited hours, and also offer advice about ...
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom Week Stay
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom Week Stay
Key West, FL
Guests staying at this villa enjoy a fitness center, a spa tub, and a garden. Staff members can answer questions about accommodations, and also provide concierge ...
Downtown Duval Street Penthouse- Private Pool-parking-roof Deck- Walk Everywhere
Downtown Duval Street Penthouse- Private Pool-parking-roof Deck- Walk Everywhere
Key West, FL
This villa features a spa tub and barbecue grills.
Tropical~tranquility
Tropical~tranquility
Key West, FL
Guests staying at this villa enjoy a water park, an outdoor tennis court, and a garden. This historic villa also has barbecue grills.
See all 1,804 Properties in Key West
Map

Luxury Villas

Book luxury villas in Key West
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Key West. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Key West, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Key West
You won’t have a problem finding your own space in Key West. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Key West on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Key West rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Hotel Options in Key West

See all 1,804 Properties in Key West

Price for 1 night 2 adults*

Oceans Edge Key West Resort, Hotel & Marina
4.0 out of 5.0
$127

Per night/room

Nov 29 - Nov 30

Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort
4.0 out of 5.0
$223

Per night/room

Dec 14 - Dec 15

Southernmost Beach Resort
The Gates Hotel Key West
4.0 out of 5.0
$107

Per night/room

Nov 29 - Nov 30

The Gates Hotel Key West
Havana Cabana at Key West
4.0 out of 5.0
$125

Per night/room

Nov 29 - Nov 30

Havana Cabana at Key West
See all 1,804 Properties in Key West

Popular Villas in 2020

Popular Winery Hotels in 2020

Popular Ski Resorts in 2020

More Places To Stay 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.