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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winter Garden villas

Outdoor dining

1. Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
The price is ￥34,042
￥48,844 total
includes taxes & fees
Aug 31 - Sep 1
Villa Near Disney World and SeaWorld
Outdoor dining

2. Luxury Villa Near Walt Disney World

Luxury Villa Near Walt Disney World
Kissimmee
The price is ￥60,800
￥80,836 total
includes taxes & fees
Aug 31 - Sep 1
Luxury Villa Near Walt Disney World
Outdoor dining

3. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is ￥23,934
￥36,213 total
includes taxes & fees
Aug 31 - Sep 1
1-Bedroom Villa Near Disney w/ Pool & Lazy River
A heated pool

4. 4,800 sf Estate | Pool, Lake, Weddings and Events

4,800 sf Estate | Pool, Lake, Weddings and Events
Orlando
9.8 out of 10, Exceptional, (31 reviews)
"This property is absolutely beautiful with a ton of space to hang out, relax and have fun! You won't find another place with this many options! "
United States
Hidden Gem C.
The price is ￥62,897
￥171,083 total
includes taxes & fees
Aug 10 - Aug 11
4,800 sf Estate | Pool, Lake, Weddings and Events
Villa (3 Bedrooms) | Interior

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

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥20,157
￥83,541 total
includes taxes & fees
Aug 4 - Aug 5
The Farm House - Great Location + Pet Friendly!
Exterior

6. Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees

Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Clermont
10.0 out of 10, Exceptional, (19 reviews)
"This was our second time staying here. It was clean and well stocked for the week. The pools at the place were great. We were able to enjoy pickleball and golf on the resort as well. "
United States
Carolyn B.
The price is ￥17,794
￥43,359 total
includes taxes & fees
Aug 4 - Aug 5
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Property grounds

7. Luxury Tiny by Tiny Hamptons - Chef’s Kitchen

Luxury Tiny by Tiny Hamptons - Chef’s Kitchen
Clermont
10.0 out of 10, Exceptional, (9 reviews)
"Nice accommodations, easy check in, great communications, clean and nice."
United States
John W.
The price is ￥31,323
￥60,108 total
includes taxes & fees
Aug 4 - Aug 5
Luxury Tiny by Tiny Hamptons - Chef’s Kitchen
Exterior

8. Tropical Views 4bdr Sleeps 8. Close to Parks!

Tropical Views 4bdr Sleeps 8. Close to Parks!
Eagle Pointe South
9.4 out of 10, Exceptional, (36 reviews)
"The house was as advertised. It was a nice cozy spot for us to stay and very close to the theme parks! Would def stay here again!"
United States
Angela P.
Tropical Views 4bdr Sleeps 8. Close to Parks!
Villa, 4 Bedrooms | Aerial view

9. Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home

Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home
3.0 star property
Kissimmee
The price is ￥24,813
￥99,770 total
includes taxes & fees
Aug 7 - Aug 8
Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home
Smart TV

10. Beauty 4 miles to Disney 3Br 2Ba Pool Home

Beauty 4 miles to Disney 3Br 2Ba Pool Home
Indian Wells
10.0 out of 10, Exceptional, (5 reviews)
"Spotlessly clean and very quiet. Excellent stay "
United States
Dina A.
The price is ￥37,383
￥71,895 total
includes taxes & fees
Aug 4 - Aug 5
Beauty 4 miles to Disney 3Br 2Ba Pool Home
Exterior

11. Amazing Villa with south facing pool and conservation view

Amazing Villa with south facing pool and conservation view
Watersong
9.8 out of 10, Exceptional, (221 reviews)
"Great communication. Nice pool and hot tub area."
United States
David V.
The price is ￥23,610
￥77,076 total
includes taxes & fees
Aug 5 - Aug 6
Amazing Villa with south facing pool and conservation view
Villa (3 Bedrooms) | Interior

12. Upstay Pristine 3BR Home With Private Pool & BBQ

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
The price is ￥17,558
￥45,523 total
includes taxes & fees
Aug 4 - Aug 5
Upstay Pristine 3BR Home With Private Pool & BBQ
Exterior

13. New Vista Cay Home | Universal & Convention

New Vista Cay Home | Universal & Convention
Orlando
The price is ￥26,361
￥33,145 total
includes taxes & fees
Sep 1 - Sep 2
New Vista Cay Home | Universal & Convention
A heated pool

14. Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!

Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Kissimmee
8.6 out of 10, Excellent, (89 reviews)
"It was a very nice house my family and I really enjoyed it and made beautiful memories the property manager was very quick to get back with me and helpful, it was very close and convenient to the parks. Would love to stay here again."
United States
Cheryl D.
The price is ￥28,049
￥146,461 total
includes taxes & fees
Aug 5 - Aug 6
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Villa (5 Bedrooms) | Interior

15. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥22,963
￥93,232 total
includes taxes & fees
Aug 4 - Aug 5
Rustic Hideaway - Great Location + Pet Friendly!
Exterior

16. Private Pool, Spa and Premium Resort Amenities Included!

Private Pool, Spa and Premium Resort Amenities Included!
Kissimmee
7.0 out of 10, Good, (7 reviews)
"We've stayed at a lot of vacation houses in Orlando and this is one of the best. Super new. Great resort with lots of clubhouses."
United States
Craig B.
The price is ￥52,040
￥86,060 total
includes taxes & fees
Aug 31 - Sep 1
Private Pool, Spa and Premium Resort Amenities Included!
Pool

17. 10BR Villa Near Disney, Pool and Resort Waterpark

10BR Villa Near Disney, Pool and Resort Waterpark
Kissimmee
10.0 out of 10, Exceptional, (24 reviews)
"Great place to stay"
United States
Jefferson C.
The price is ￥38,673
￥126,839 total
includes taxes & fees
Aug 5 - Aug 6
10BR Villa Near Disney, Pool and Resort Waterpark
Property grounds

18. Premium home, pool and spa, with Inclusive Resort Amenities

Premium home, pool and spa, with Inclusive Resort Amenities
Watersong
9.8 out of 10, Exceptional, (13 reviews)
"As Advertised. Had a great time at this beautiful home."
United States
Julio M.
The price is ￥52,513
￥84,124 total
includes taxes & fees
Aug 23 - Aug 24
Premium home, pool and spa, with Inclusive Resort Amenities
Villa, Multiple Bedrooms | Aerial view

19. 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 ￥39,100
￥179,541 total
includes taxes & fees
Aug 17 - Aug 18
Water Kingdom @ Storey Lake By Shine Villas! #525 9 Bedroom Home
Pool

20. Premium Architecture | 3 Masters | 15 Min Disney

Premium Architecture | 3 Masters | 15 Min Disney
Kissimmee
The price is ￥89,088
￥159,523 total
includes taxes & fees
Aug 4 - Aug 5
Premium Architecture | 3 Masters | 15 Min 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 Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Great stay! Will definitely come back. Alianna made our check-in smooth and fun. She has great customer service skills. Breakfast at the Valencia was 10/10. Room was clean, beautiful, and smelled very nice."
Chutney 3-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews
454
Accommodation
10710 Villas
Lowest Price
￥33,145
Highest Price
￥179,541

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between ￥33,145 and ￥179,541 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.