Compare Winter Park 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 Winter Park

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities.

Pool

Kitchen

Ultimate Lakeview Villa with Everything!

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities.

Pool

Kitchen

This villa offers a water park, a gym, and an arcade/game room. This family-friendly villa also has laundry facilities.

Pool

Kitchen

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities.

Pool

Kitchen

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities.

Pool

Kitchen

Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities.

Pool

Kitchen

At this villa, guests enjoy an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.

Pool

Hot Tub

At this villa, guests enjoy features like an outdoor pool, a gym, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and local meal delivery service.

Pool

Hot Tub

Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney

Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and barbecue grills.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Winter Park

View all properties

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 Winter Park

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

$123 nightly

$139 total

May 5 - May 6

Total with taxes and fees

9.2/10 Wonderful! (5,168 reviews)

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

$229 nightly

$258 total

Apr 26 - Apr 27

Total with taxes and fees

9.4/10 Exceptional! (4,112 reviews)

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

$133 nightly

$150 total

May 10 - May 11

Total with taxes and fees

9/10 Wonderful! (6,663 reviews)

Luxury Villas

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

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

A top-end villa experience in Winter Park 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!

Winter Park Villas essential information

Accommodation	1461 Villas
Lowest Price	$139
Highest Price	$258
Popular accommodation	Modern Luxury Villa with Everything, Ultimate Lakeview Villa with Everything!, Modern Luxury Villa with Everything, Lakeview Luxury Villa with Everything!, Lakeview Luxury Villa with Everything!, Lakeview Luxury Villa with Everything, 6 Miles to Disneys, Large Family home with a Private Pool and Spa,CHECK THIS OUT, Beautiful Home, 6-Bdrms, 5-Baths, Very Near Disney, Private Pool and Spa, Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney