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Featured Villas in Windermere

Near Disney Dream Home With Pool
Near Disney Dream Home With Pool
4.0 out of 5.0 4622 Terrasonesta Drive, Davenport, FL
Near Disney Dream Home With Pool features an indoor pool, an outdoor pool, and a children's pool. Free parking is included with your stay. Additional amenities ...
Brand New/pool/clubhouse/communalsurf Rider/slides/gym/teen Hanghout/1st Class
Brand New/pool/clubhouse/communalsurf Rider/slides/gym/teen Hanghout/1st Class
Lake Buena Vista, FL
At this villa, guests have access to a fitness center and a garden.
Tropical Oaks Villa
Tropical Oaks Villa
4.0 out of 5.0 4129 Southern Oaks Ct, Kissimmee, FL
Guests of this villa enjoy 2 outdoor pools, an indoor pool, and a 24-hour fitness center. There's free parking if you drive. The front desk is staffed 24/7 to ...
Villa Near Walt Disney World Resort and Seaworld With 52 Holes of Golf
Villa Near Walt Disney World Resort and Seaworld With 52 Holes of Golf
Winter Garden, FL
At this villa, guests have access to a spa tub, an outdoor tennis court, and an arcade/game room.
Luxury Villa With Pool-game Room Near Disney World
Luxury Villa With Pool-game Room Near Disney World
Kissimmee, FL
At this villa, guests have access to features like an arcade/game room.
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/spa/wifi
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/spa/wifi
Kissimmee, FL
Guests of this villa enjoy features like a fitness center, a spa tub, and an arcade/game room.
Kissimmee Vacation Homes
Kissimmee Vacation Homes
3.5 out of 5.0 Funie Steed Rd, Kissimmee, FL
At Kissimmee Vacation Homes, guests have access to an outdoor pool and a garden. If you drive, put free parking to good use.
Luxury 4 BR Gated Villa 5 Miles From Disney Wifi
Luxury 4 BR Gated Villa 5 Miles From Disney Wifi
Kissimmee, FL
Guests staying at this resort enjoy a fitness center, a spa tub, and an outdoor tennis court. This resort also has a computer station.
Luxury 4 BR Gated Villa 5 Miles From Disney Wifi
Luxury 4 BR Gated Villa 5 Miles From Disney Wifi
Kissimmee, FL
Guests staying at this resort enjoy a fitness center, a spa tub, and an outdoor tennis court. This resort also has a computer station.
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Luxury Villas

Book luxury villas in Windermere
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Windermere. 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 Windermere, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Windermere
You won’t have a problem finding your own space in Windermere. 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 Windermere on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Windermere 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 Windermere

See all 38,560 Properties in Windermere
*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.