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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winter Garden villas

Outdoor dining

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
1-Bedroom Villa Near Disney w/ Pool & Lazy River
Outdoor dining

2. Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
Villa Near Disney World and SeaWorld
Outdoor dining

3. Luxury Villa Near Walt Disney World

Luxury Villa Near Walt Disney World
Kissimmee
The price is €425
includes taxes & fees
28 Aug - 29 Aug
Luxury Villa Near Walt Disney World
BBQ/picnic Area

4. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
Rustic Hideaway - Great Location + Pet Friendly!
Exterior

5. 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 €244
includes taxes & fees
25 Sept - 26 Sept
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Villa (3 Bedrooms) | Interior

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

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
The price is €271
includes taxes & fees
8 Sept - 9 Sept
Upstay Pristine 3BR Home With Private Pool & BBQ
Microwave, oven, stovetop, dishwasher

7. Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking

Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking
Mount Dora
10.0 out of 10, Exceptional, (4 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 €211
includes taxes & fees
7 Sept - 8 Sept
Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking
Exterior

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

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.2 out of 10, Wonderful, (7 reviews)
"It had everything we needed, and more. It was very pet-friendly. The host was very polite and discreet. Clean and neat. The location cannot be more centric for shops and so on. And, it is a bargain. We wanted to stay lomger, but it was already booked!"
United States
Maria M.
The price is €161
includes taxes & fees
3 Sept - 4 Sept
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Exterior

9. Charming Villa near Disney, pool, 4 beds, sleeps 5

Charming Villa near Disney, pool, 4 beds, sleeps 5
Vacation Village
8.6 out of 10, Excellent, (4 reviews)
"Excellent stay and host. A short stay but we really like the home! No complaints and the host was super friendly and helpful."
United States
Joe H.
The price is €223
includes taxes & fees
30 Aug - 31 Aug
Charming Villa near Disney, pool, 4 beds, sleeps 5
Exterior

10. Completely Renovated 3/2 Close to Disney parks

Completely Renovated 3/2 Close to Disney parks
Royal Palm Bay
10.0 out of 10, Exceptional, (35 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
The price is €204
includes taxes & fees
30 Aug - 31 Aug
Completely Renovated 3/2 Close to Disney parks
A heated pool

11. Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ

Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ
Clermont
9.8 out of 10, Exceptional, (21 reviews)
"The property was immaculate, very roomy and modern . Pool was warm and house was very family Friendly. Host was very responsive "
United Kingdom
Donna C.
The price is €979
includes taxes & fees
28 Aug - 29 Aug
Luxurious Brand New 8 Bed 6 Bath Disney Theme Villa With Free Heated Pool & BBQ
A heated pool

12. 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, (32 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 €932
includes taxes & fees
8 Sept - 9 Sept
4,800 sf Estate | Pool, Lake, Weddings and Events
Terrace/patio

13. 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
9.0 out of 10, Wonderful, (2 reviews)
"Enjoyed our stay .. was clean and had all the amenities"
United States
Ayman
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
Villa (4 Bedrooms) | Interior

14. Emerald Garden - Resort - 15 Min to Disney - Pets

Emerald Garden - Resort - 15 Min to Disney - Pets
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €353
includes taxes & fees
30 Aug - 31 Aug
Emerald Garden - Resort - 15 Min to Disney - Pets
Property grounds

15. 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 €336
includes taxes & fees
28 Aug - 29 Aug
Luxury Tiny by Tiny Hamptons - Chef’s Kitchen
Villa (4 Bedrooms) | Interior

16. Spacious Townhome Near Disney, Free Parking

Spacious Townhome Near Disney, Free Parking
3.5 star property
Regal Palms
8.0 out of 10, Very good, (1 review)
"The unit was clean. The host was responsive. The resort property was fun and welcoming. Definitely enjoyed the pool area. Location was pretty good for all the things we wanted to do. The check-in check-out process was pretty smooth. I would definitely stay here again when I visit this area."
United States
Marquita
The price is €265
includes taxes & fees
7 Sept - 8 Sept
Spacious Townhome Near Disney, Free Parking
Villa, 4 Bedrooms | Exterior

17. Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa

Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa
3.0 star property
Highlands Reserve
9.0 out of 10, Wonderful, (2 reviews)
"Spacious and homey. After a terrible start we ended it well at this place which feels like home and very scenic backyard sunrise in the pool whilst working out was amazing so was sunsets if you love nature but privacy not too much as I would like in the back yard"
United States
Belkis
Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa
A heated pool

18. 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 €803
includes taxes & fees
29 Aug - 30 Aug
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Interior

19. At Lakes Upscale Villa/Next to Downtown Orlando

At Lakes Upscale Villa/Next to Downtown Orlando
Lake Davis - Greenwood
10.0 out of 10, Exceptional, (28 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
The price is €428
includes taxes & fees
6 Sept - 7 Sept
At Lakes Upscale Villa/Next to Downtown Orlando
Exterior

20. 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 €392
includes taxes & fees
30 Aug - 31 Aug
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, 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 Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"I researched where to stay using AI and specifically asked for a resort that would be efficient, effortless and incredibly fun and engaging for my family of 8 that are all different ages and generations, and The Grove delivered in a great way! Ages ranged from 1 - 66 and we all were entertained had so much fun and we never left the resort honestly one of the best family vacations we’ve had. We are looking forward to making this an annual tradition."
Samantha 7-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
265
Accommodation
10022 Villas
Lowest Price
€161
Highest Price
€979

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between €161 and €979 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. Travelling 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 travellers' 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.

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