Search Villas in Winter Garden

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winter Garden villas

A patio area with striped umbrellas, green chairs, a table, and a sign reading "CABANA 6".

1. Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
The price is ￥41,329
￥55,629 total
includes taxes & fees
Dec 3 - Dec 4
Villa Near Disney World and SeaWorld
A patio area with striped umbrellas, green chairs, a table, and a sign reading "CABANA 6".

2. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is ￥27,860
￥39,847 total
includes taxes & fees
Nov 16 - Nov 17
1-Bedroom Villa Near Disney w/ Pool & Lazy River
A patio area with striped umbrellas, green chairs, a table, and a sign reading "CABANA 6".

3. Luxury Villa Near Walt Disney World

Luxury Villa Near Walt Disney World
Kissimmee
The price is ￥103,135
￥127,996 total
includes taxes & fees
Nov 27 - Nov 28
Luxury Villa Near Walt Disney World
A modern bathroom with two sinks, wooden cabinets, and a glass shower enclosure.

4. Family Vacation Home Near Disney With Resort Pool

Family Vacation Home Near Disney With Resort Pool
3.0 star property
Orlando
The price is ￥14,717
￥58,900 total
includes taxes & fees
Nov 16 - Nov 17
Family Vacation Home Near Disney With Resort Pool
BBQ/picnic area

5. 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
The price is ￥25,198
￥95,786 total
includes taxes & fees
Nov 9 - Nov 10
Rustic Hideaway - Great Location + Pet Friendly!
A swimming pool with a football on the edge, surrounded by a covered area with a view of trees and a building in the background.

6. 129 Seneca Point Trl

129 Seneca Point Trl
4.0 star property
Indian Point
The price is ￥17,102
￥62,545 total
includes taxes & fees
Nov 18 - Nov 19
129 Seneca Point Trl
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing natural light.

7. Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes

Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes
Mount Dora
10.0 out of 10, Exceptional, (5 reviews)
"Great comfortable place! Clean, nicely appointed and great location for Mt Dora downtown, Rennigers, and Kings Landing."
United States
Debbie T.
The price is ￥12,757
￥39,248 total
includes taxes & fees
Dec 6 - Dec 7
Mount Dora Escape • Private Acre & Boat Parking - Vista Vibes
The exterior of Altamonte Mall with a large green sign, palm trees, and a curved entrance.

8. Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed my stay, was super quiet, and very conveniently located to everywhere I needed to go in Seminole County. The host was great with communication and provided everything I needed to have a great stay."
United States
Brian
The price is ￥12,757
￥26,698 total
includes taxes & fees
Nov 11 - Nov 12
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
A residential house with a blue exterior, a white garage door, and a driveway.

9. Heated Pool Game Room Home Near Disney

Heated Pool Game Room Home Near Disney
2.0 star property
Aylesbury
Heated Pool Game Room Home Near Disney
A covered patio with a sofa, chairs, and a small table.

10. Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College

Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
Winter Park
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay .. was clean and had all the amenities"
United States
Ayman
The price is ￥20,022
￥49,158 total
includes taxes & fees
Nov 18 - Nov 19
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

11. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is ￥12,799
￥49,719 total
includes taxes & fees
Nov 10 - Nov 11
Amazing Spider | Disney, Slides & River
A covered outdoor swimming pool with lounge chairs and a pergola structure.

12. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
8.8 out of 10, Excellent, (21 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is ￥15,749
￥66,303 total
includes taxes & fees
Nov 8 - Nov 9
Gorgeous VILLA near Disney, Private Heated South Pool
Exterior

13. Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom

Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is ￥23,151
￥67,799 total
includes taxes & fees
Nov 15 - Nov 16
Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
A two-story residential building with a stone facade, multiple windows, and a well-maintained garden.

14. Townhome With Resort Pool & Mini Golf by Disney

Townhome With Resort Pool & Mini Golf by Disney
3.0 star property
Orlando
The price is ￥16,205
￥60,574 total
includes taxes & fees
Nov 30 - Dec 1
Townhome With Resort Pool & Mini Golf by Disney
A two-story house with a paved driveway and a lawn.

15. The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is ￥25,336
￥89,733 total
includes taxes & fees
Nov 9 - Nov 10
The Farm House - Great Location + Pet Friendly!
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

16. Cozy 3BD Townhouse Near Disney, Encantada Resort

Cozy 3BD Townhouse Near Disney, Encantada Resort
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"I was looking for a place to escape for a few days while getting my bathroom redone and the property checked all of the boxes. My wife was able to get some work done, my dog had more than enough space, and the location is minutes from the amusement parks and tons of restaurants.The property is gated, clean, and has multiple bedrooms and bathrooms for the larger families that need it. The host was more than attentive. Even when I was having issues with the television, he responded to my message...
United States
LEONARD W.
The price is ￥9,607
￥51,822 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 3BD Townhouse Near Disney, Encantada Resort
A hot tub with a view of a lake and surrounding trees.

17. 4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando

4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Overall it was great stay. Initially there was an issue with the door when we checked in, but the host fixed it write away. The house was very clean and had everything we needed plus more. I would definitely book again."
United States
Silvia R.
The price is ￥45,672
￥98,667 total
includes taxes & fees
Dec 3 - Dec 4
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
A two-story house with a garage, stone accents, and a well-maintained lawn.

18. Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!

Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Davenport
9.0 out of 10, Wonderful, (78 reviews)
"This property was more than expected and we plan to come again because we loved the house and the resort."
United States
Kimberly J.
The price is ￥23,657
￥124,925 total
includes taxes & fees
Nov 18 - Nov 19
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
A two-story house with a red garage, surrounded by a well-maintained lawn and trees.

19. Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Trafalgar Village
8.8 out of 10, Excellent, (12 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is ￥15,119
￥71,357 total
includes taxes & fees
Nov 8 - Nov 9
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Terrace/patio

20. 🌿Welcome to the Jungle🌿

🌿Welcome to the Jungle🌿
Loughman
9.0 out of 10, Wonderful, (20 reviews)
"Hosts were great and very responsive! Our family loved our stay, house was nice and plenty of room for all of us! We would definitely stay here again! Thank you for being such great hosts!"
United States
Amanda P.
The price is ￥22,090
￥70,601 total
includes taxes & fees
Nov 9 - Nov 10
🌿Welcome to the Jungle🌿
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.
View all properties

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
A brick building with a clock tower and a sign that reads "Winter Garden."

Top reviews in Winter Garden

A modern multi-story residential building with a symmetrical facade, stone accents, and a central entrance.
Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms
Clermont

10/10 Excellent

Even better than what is shown
United States
Malyjah
Reviewed July 5, 2026
Contemporary 4BR Townhome With Pool & Themed Rooms

Frequently Asked Questions

How much do villas in Winter Garden cost?

Villas in Winter Garden cost between ￥9,607 and ￥103,135 per night. These stays offer the privacy to enjoy your own space at a price that's gentle to your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your villa in Winter Garden with Expedia?

With Expedia, it's easy to find your ideal villa in Winter Garden. Traveling with the kids? Use our helpful filters to search for stays with amenities like a pool and WiFi. If you have a budget, choose how much you're willing to spend and your preferred star rating. We'll help you find the right place in tune with your taste and style.

How can I find cheap villas in Winter Garden?

A great way to get cheap villas in Winter Garden is with Expedia's convenient filter tool. Refine your search results by star rating, budget and amenities to grab awesome bargains in only a click or two.

What is there to do near my villa in Winter Garden?

Whatever your tastes or interests, Winter Garden has lots of things to keep you busy. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on most travelers' sightseeing plans. You shouldn't miss Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you can discover more terrific attractions like these with the money you save.