Search Villas in Winter Park

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 1289 Villas in Winter Park with updated reviews, rates, and availability.

Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (348)
"This was our first time staying there and we’ve been to many other places and we loved this one by far!!! Everything was great. Just wish there were dressers to put our clothes in thanks"
Lakeview Luxury Villa with Everything
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (400)
"We enjoyed our stay here. The location was great and the house was perfect for our large family. Would definitely stay here again. "
Modern Luxury Villa with Everything
Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (83)
"Plenty of room and things to do. House was perfect for our large extended family. "
Lakeview Luxury Villa with Everything
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (347)
"Very clean and quiet location! Close to the parks and restaurants. The pool area on the property was very fun and convenient for our 3 year old! "
Ultimate Lakeview Villa with Everything!
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (219)
"Our stay was a family Christmas gift. There was something for everyone to do without having to leave the property. Wecwill definately stay here again. "
Modern Luxury Villa with Everything
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (107)
"Property was as described but best of all everything we needed was close by."
Ultimate Lakeview Villa with Everything!
Beautiful lake view villa
Outdoor pool, a heated pool

Beautiful lake view villa

9.2 out of 10, Wonderful, (75)
"Great property! Within 30 minutes of all major attractions in the area. Lots of space, clean, screened pool area, quiet neighborhood. This was our second stay at this house and we would definitely stay there again!"
Beautiful lake view villa
****** Close to Disney and Universal*******
Exterior

****** Close to Disney and Universal*******

9.8 out of 10, Exceptional, (95)
"Excellent location, the house is full equipted, we made turkey for Thanksgiving even!. Tons of amenites to use, parking space. The host was super responsive, always checking and answering our questions. We had a great time! Thanks!"
****** Close to Disney and Universal*******
Lakeview Luxury Villa with Everything!
Pool

Lakeview Luxury Villa with Everything!

9.6 out of 10, Exceptional, (86)
"The rental was perfect for our requirements."
Lakeview Luxury Villa with Everything!
Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba
Outdoor pool, a heated pool

Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba

9.2 out of 10, Wonderful, (23)
"close to everything shopping, parks, a safe and family place"
Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba
Walk to Lake: Stunning Central Florida Home!
Outdoor pool

Walk to Lake: Stunning Central Florida Home!

10.0 out of 10, Exceptional, (45)
"House is beautiful and staff fantastic"
Walk to Lake: Stunning Central Florida Home!
Villa in Kissimmee next to Disney!
Pool

Villa in Kissimmee next to Disney!

8.2 out of 10, Very Good, (20)
"Great location, great host , "
Villa in Kissimmee next to Disney!
Lakeview Luxury Villa in Storey Lake
Pool

Lakeview Luxury Villa in Storey Lake

9.8 out of 10, Exceptional, (23)
"Great hostClean homePrompt to answer questionsSimpe check-in and check out processWould definitely come back to stay on our next trip to the area"
Lakeview Luxury Villa in Storey Lake
Free Shuttle,Official Encore Water Park,XBOX,Movie,Games,Cage,Pool/Spa,Star Wars
Outdoor pool

Free Shuttle,Official Encore Water Park,XBOX,Movie,Games,Cage,Pool/Spa,Star Wars

9.8 out of 10, Exceptional, (76)
"Disney"
Free Shuttle,Official Encore Water Park,XBOX,Movie,Games,Cage,Pool/Spa,Star Wars
Unbeatable Location: Your Dream Villa Next to SeaWorld
Microwave, oven, stovetop, dishwasher

Unbeatable Location: Your Dream Villa Next to SeaWorld

9.4 out of 10, Exceptional, (56)
"Stayed here for one night after a concert. It's a great, safe location and the accommodations are plenty. Definitely recommend for a stay."
Unbeatable Location: Your Dream Villa Next to SeaWorld
Modern Luxury Villa in Storey Lake
Pool

Modern Luxury Villa in Storey Lake

9.4 out of 10, Exceptional, (40)
"I have been going to Disney world every year for the last 15 years and let me tell you this house has been the best ever, perfect location, very nice house all the way around. Definitely coming back to this property. My kids love the house amenities. "
Modern Luxury Villa in Storey Lake
Resort style family friendly vacation villa
TV

Resort style family friendly vacation villa

9.6 out of 10, Exceptional, (7)
"Great location and everything is functional. The property just needs some TLC to fix it up and replace some of the stains. "
The price is SAR 386
SAR 1,446 total
includes taxes & fees
24 Apr - 25 Apr
Resort style family friendly vacation villa
Vista Cay Modern
Outdoor pool

Vista Cay Modern

4.0 star property
10.0 out of 10, Exceptional, (2)
"Es una muy buena opción para una família de hasta 6 personas. Es una urbanización en una muy buena ubicación, segura y con buenas instalaciones (la piscina está en remodelación). Hay todo en la casa que se necesita para una família. "
Vista Cay Modern
6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More
Exterior

6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More

9.8 out of 10, Exceptional, (34)
"We held a birthday party here and this property was absolutely perfect. The pool was fantastic, and the courtyard area was great to setup games. Very happy with the space both indoor & outdoor and the communication from the hosts. 10/10 would recommend and would book again."
6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More
Perfect family two story Villa 8 near SeaWorld
Outdoor pool, a heated pool

Perfect family two story Villa 8 near SeaWorld

9.6 out of 10, Exceptional, (72)
"Clean affordable easy check in Nice area gate for safety "
Perfect family two story Villa 8 near SeaWorld
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.
Don't see what you're looking for?
See all available properties in Winter Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winter Park

Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8612)
"Great place , near places, lots to offer "
The price is SAR 638
SAR 829 total
includes taxes & fees
24 Apr - 25 Apr
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1879)
"Great place to stay "
The price is SAR 699
SAR 883 total
includes taxes & fees
27 Apr - 28 Apr
Florida Hotel & Conference Center in the Florida Mall
The View Studio Suites and Event Venue
Exterior

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (1031)
"Nice place to stay! "
The price is SAR 300
SAR 337 total
includes taxes & fees
27 Apr - 28 Apr
The View Studio Suites and Event Venue
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.

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.