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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Garden villas

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

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is NZ$489
includes taxes & fees
4 Oct - 5 Oct
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".

2. Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
Villa Near Disney World and SeaWorld
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 NZ$1,024
includes taxes & fees
7 Oct - 8 Oct
Luxury Villa Near Walt Disney World

4. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is NZ$990
includes taxes & fees
28 Sept - 29 Sept
Rustic Hideaway - Great Location + Pet Friendly!

5. 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 NZ$448
includes taxes & fees
27 Sept - 28 Sept
Charming Villa near Disney, pool, 4 beds, sleeps 5
A modern multi-story residential building with a symmetrical facade, stone accents, and a central entrance.

6. Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms
3.5 star property
Clermont
10.0 out of 10, Exceptional, (1 review)
"Even better than what is shown"
United States
Malyjah
The price is NZ$578
includes taxes & fees
14 Oct - 15 Oct
Contemporary 4BR Townhome With Pool & Themed Rooms
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing natural light.

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 NZ$414
includes taxes & fees
20 Oct - 21 Oct
Vista Vibes • Boutique Escape Near Lake Dora • Acreage & Boat Parking
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 NZ$323
includes taxes & fees
26 Sept - 27 Sept
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
A poolside area with a covered seating area, a pool, and a view of a body of water.

9. 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 NZ$1,809
includes taxes & fees
28 Sept - 29 Sept
4,800 sf Estate | Pool, Lake, Weddings and Events
A two-story building with a white picket fence, a staircase, and a clear sky.

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, (36 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
Completely Renovated 3/2 Close to Disney parks
A covered swimming pool with a view of a grassy area and trees.

11. 7BR Lakefront | Pool & Hot Tub

7BR Lakefront | Pool & Hot Tub
Edgewood
9.8 out of 10, Exceptional, (21 reviews)
"Check in was very easy and the location was great, close to everything we wanted to do.The property had lots to offer and was in a nice quiet neighborhood."
United States
Omer H.
The price is NZ$1,068
includes taxes & fees
27 Sept - 28 Sept
7BR Lakefront | Pool & Hot Tub
A hotel entrance with a central fountain, palm trees, and a clear blue sky.

12. 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 NZ$832
includes taxes & fees
27 Sept - 28 Sept
Amazing Villa with south facing pool and conservation view
A covered patio with a sofa, chairs, and a small table.

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
The price is NZ$584
includes taxes & fees
14 Oct - 15 Oct
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
A residential complex with multiple houses, a parking area, and a swimming pool.

14. Storey Lake Resort~Heated Pool~Brand New~Designer

Storey Lake Resort~Heated Pool~Brand New~Designer
Kissimmee
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Host was very attentive and responded back quickly anytime we had a question before or during our stay. Resort amenities were wonderful and location was great! We would stay again! "
United States
Amber K.
The price is NZ$827
includes taxes & fees
12 Oct - 13 Oct
Storey Lake Resort~Heated Pool~Brand New~Designer
A clear, enclosed swimming pool with a 5 FT depth marker, surrounded by a metal frame and glass walls, with a grassy area and buildings in the background.

15. 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, (90 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 NZ$1,595
includes taxes & fees
30 Sept - 1 Oct
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
A modern building with a stone facade, multiple windows, and a parking lot.

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

Upstay Pristine 3BR Home With Private Pool & BBQ
3.5 star property
Clermont
The price is NZ$509
includes taxes & fees
28 Sept - 29 Sept
Upstay Pristine 3BR Home With Private Pool & BBQ
An aerial view of a resort with a swimming pool, sun loungers, and a red-roofed building.

17. Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island

Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island
Kissimmee
8.6 out of 10, Excellent, (14 reviews)
"Beautiful resort, great location"
United States
Sandra A.
The price is NZ$844
includes taxes & fees
7 Oct - 8 Oct
Paradise Found: Luxurious 5-Bedroom / 3 Bath Retreat with Pool in Emerald Island
A modern kitchen with a bar area, a dining space, and a living area with a fireplace.

18. 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, (31 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
The price is NZ$911
includes taxes & fees
29 Sept - 30 Sept
At Lakes Upscale Villa/Next to Downtown Orlando
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with two chairs.

19. Family Friendly Villa near Disney, pool, sleeps 5

Family Friendly Villa near Disney, pool, sleeps 5
Vacation Village
9.0 out of 10, Wonderful, (2 reviews)
"It was clean. "
United States
Amy E.
Family Friendly Villa near Disney, pool, sleeps 5
A modern living room with a brown leather sofa, a glass coffee table, and blue chairs. There is a dining area with a glass table and white plates. A chandelier hangs from the ceiling, and a clock is on the wall.

20. 3BR Townhouse Right in Front of Epic Universe!

3BR Townhouse Right in Front of Epic Universe!
Orlando
9.6 out of 10, Exceptional, (15 reviews)
"Easy access for all we did the week we stayed. Great rooms, it was wonderful to be so comfortable."
United States
Hal J.
The price is NZ$773
includes taxes & fees
28 Sept - 29 Sept
3BR Townhouse Right in Front of Epic Universe!
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"So much to do here and see. The property is fantastic and family friendly. We will be back."
DANIEL 2-night trip
Posted 7 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews
486
Accommodation
10024 Villas
Lowest Price
NZ$323
Highest Price
NZ$1,809

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between NZ$323 and NZ$1,809 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.
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.