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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winter Park villas

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 ₩129,915
₩399,990 total
includes taxes & fees
May 21 - May 22
Upstay Modern 3BR Townhome With Pool Near Disney
Villa, 4 Bedrooms | Exterior

Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse

Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse
3.0 star property
Kissimmee
The price is ₩175,221
₩986,113 total
includes taxes & fees
May 20 - May 21
Blue Beach At Storey Lake By Shine Villas #400 4 Bedroom Townhouse
Villa (3 Bedrooms) | Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ₩183,852
₩784,257 total
includes taxes & fees
May 20 - May 21
The Farm House - Great Location + Pet Friendly!
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 ₩341,155
₩1,779,347 total
includes taxes & fees
Jun 3 - Jun 4
Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
Villa (5 Bedrooms) | Interior

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ₩227,680
₩895,555 total
includes taxes & fees
May 25 - May 26
Rustic Hideaway - Great Location + Pet Friendly!
Villa (4 Bedrooms) | Interior

Upstay: Resort Home w Private Pool Near Disney

Upstay: Resort Home w Private Pool Near Disney
3.0 star property
Kissimmee
The price is ₩274,764
₩632,188 total
includes taxes & fees
May 30 - May 31
Upstay: Resort Home w Private Pool Near Disney
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Love the resort and all the pools. Something for everyone! Feels like a home! "
Angela 3-night trip
Posted 2 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Park

Winter Park Villas information

Number of reviews
Accommodation
582 Villas
Lowest Price
₩399,990
Highest Price
₩1,779,347

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.