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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winter Park villas

A row of townhouses with green awnings, a curved pathway, and well-maintained landscaping.

1. Family Vacation Home Near Disney w Pool & Spa

Family Vacation Home Near Disney w Pool & Spa
3.0 star property
Orlando
The price is ₩140,096
₩516,354 total
includes taxes & fees
Nov 1 - Nov 2
Family Vacation Home Near Disney w Pool & Spa
BBQ/picnic area

2. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
8.0 out of 10, Very good, (1 review)
"Good house for a great price. Great location. Need to change the AC more often."
United States
Mercedes
Rustic Hideaway - Great Location + Pet Friendly!
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

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"The staff were super helpful and friendly!!! Everything about our stay was excellent!!!"
Richard 2-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Winter Park

Winter Park Villas information

Number of reviews
1
Accommodation
624 Villas
Lowest Price
Highest Price

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.