A two-story house with a balcony, surrounded by lush greenery and trees.

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winter Park villas

Villa (5 Bedrooms) | Interior

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ₩232,024
₩901,177 total
includes taxes & fees
Jul 15 - Jul 16
Rustic Hideaway - Great Location + Pet Friendly!
Villa (3 Bedrooms) | Interior

Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.0 star property
Kissimmee
The price is ₩179,400
₩456,445 total
includes taxes & fees
Jul 21 - Jul 22
Upstay Modern 3BR Townhome With Pool Near Disney
Villa, Multiple Bedrooms | Aerial view

Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home

Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ₩317,593
₩1,751,040 total
includes taxes & fees
Aug 12 - Aug 13
Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
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.
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Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Excellent family friendly location"
Etienne 3-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Park

Winter Park Villas information

Number of reviews
Accommodation
590 Villas
Lowest Price
₩456,445
Highest Price
₩1,751,040

Frequently asked questions

Why book your villa in Winter Park with Expedia?
With Expedia, it's easy to find your ideal villa in Winter Park. Traveling with the kids? Use our handy filters to look for stays with amenities like WiFi and a pool. If you have a set budget, choose how much you'd like to spend and the star rating of the property. We'll help you find the perfect fit in tune with your style and taste.
How can I find cheap villas in Winter Park?
The best way to compare cheap villas in Winter Park is with Expedia's useful filter tool. Narrow your search by amenities, star rating and budget to access awesome deals in only a click or two.
What is there to do near my villa in Winter Park?
Whatever you love to do, Winter Park has loads of things to keep you going. Winter Park Country Club, Crealde School of Art and Winter Park Village are on most travelers' agendas. Don't leave without exploring Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens either. With Expedia's Winter Park hotel deals, you can see more neat attractions like these with the cash you save.