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Our top choices for Winter Park villas

Villa (3 Bedrooms) | Interior
Upstay Modern 3BR Townhome With Pool Near Disney

Villa in Kissimmee

Upstay Modern 3BR Townhome With Pool Near Disney
3.0 star property
The price is ₩165,791
₩431,978 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Upstay Modern 3BR Townhome With Pool Near Disney
Villa, Multiple Bedrooms | Aerial view
Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home

Villa in Kissimmee

Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is ₩636,118
₩2,149,566 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
Villa (4 Bedrooms) | Interior
Upstay: Family-friendly 4BR Townhouse w Pool & BBQ

Villa in Kissimmee

Upstay: Family-friendly 4BR Townhouse w Pool & BBQ
3.0 star property
The price is ₩282,565
₩629,969 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Upstay: Family-friendly 4BR Townhouse w Pool & BBQ
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

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Thre room was spacious and spotless. the tub was wonderful. multiple baths helps get the family ready to go early. Pool is freat for down days. Helpful store on site for quick needs.Location is beautiful and safe. Stayed 2 times and would stay again. "
Cynthia 4-night trip
Posted 7 hours ago
Lake Buena Vista Resort Village & Spa

Find out more about Winter Park

Winter Park Villas information

Number of reviews
Accommodation
484 Villas
Lowest Price
₩2,149,566
Highest Price
₩2,149,566

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.