Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Winter Garden villas

Outdoor dining

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is ￥29,462
￥44,342 total
includes taxes & fees
Jun 22 - Jun 23
1-Bedroom Villa Near Disney w/ Pool & Lazy River
Outdoor dining

Villa Near Disney World and SeaWorld

Villa Near Disney World and SeaWorld
Kissimmee
The price is ￥40,565
￥57,954 total
includes taxes & fees
Jun 17 - Jun 18
Villa Near Disney World and SeaWorld
Outdoor dining

Luxury Villa Near Walt Disney World

Luxury Villa Near Walt Disney World
Kissimmee
The price is ￥67,955
￥92,133 total
includes taxes & fees
Jul 15 - Jul 16
Luxury Villa Near Walt Disney World
Villa (3 Bedrooms) | Interior

The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥20,309
￥84,839 total
includes taxes & fees
Jun 22 - Jun 23
The Farm House - Great Location + Pet Friendly!
Outdoor dining

VedaHive Luxury Villa

VedaHive Luxury Villa
3.0 star property
Solterra Resort
7.6 out of 10, Good, (12 reviews)
"All inclusive good "
United States
Nelson
The price is ￥6,490
￥27,042 total
includes taxes & fees
Jun 26 - Jun 27
VedaHive Luxury Villa
Microwave, oven, stovetop, dishwasher

Vista Vibes • Upscale Escape · Lake Dora

Vista Vibes • Upscale Escape · Lake Dora
Mount Dora
10.0 out of 10, Exceptional, (3 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 ￥11,537
￥37,355 total
includes taxes & fees
Jun 17 - Jun 18
Vista Vibes • Upscale Escape · Lake Dora
Exterior

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 ￥16,593
￥42,292 total
includes taxes & fees
Jun 17 - Jun 18
Clermont Tiny Home: Main Floor Queen, Lofts & No Pet Fees
Villa, 4 Bedrooms | Aerial view

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 ￥20,902
￥103,280 total
includes taxes & fees
Jun 17 - Jun 18
Gilded Parasol By Shine Villas Remington Golf #410 4 Bedroom Home
Exterior

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, (217 reviews)
"Excellent Host. Great spot. Everything you need. "
Canada
Ken D.
The price is ￥25,491
￥80,122 total
includes taxes & fees
Jun 17 - Jun 18
Amazing Villa with south facing pool and conservation view
Exterior

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, (10 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is ￥15,383
￥75,648 total
includes taxes & fees
Jun 21 - Jun 22
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior

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, (69 reviews)
"We had an excellent stay at this property. Everything was very clean, well-maintained, and exactly as described. The resort itself is great, with a very comfortable and enjoyable atmosphere. A couple of small improvements could make the experience even better: providing more toilet paper, especially for larger groups, and including propane for the BBQ grill would be a nice added touch. Overall, we had a great experience and would definitely recommend this property to others."
United States
Jorge
The price is ￥32,449
￥143,160 total
includes taxes & fees
Jun 21 - Jun 22
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Exterior

SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
College Park
10.0 out of 10, Exceptional, (29 reviews)
"Great place and super nice host. Definitely recommend this place if you're ever in Orlando"
United States
Keri G.
The price is ￥18,924
￥28,822 total
includes taxes & fees
Jun 21 - Jun 22
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
Villa (4 Bedrooms) | Interior

Upstaymodern 4BR Family Townhome w Private Pool

Upstaymodern 4BR Family Townhome w Private Pool
3.0 star property
Clermont
The price is ￥22,113
￥58,162 total
includes taxes & fees
Jun 17 - Jun 18
Upstaymodern 4BR Family Townhome w Private Pool
Villa (5 Bedrooms) | Interior

Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
3.0 star property
Windermere
The price is ￥23,638
￥95,240 total
includes taxes & fees
Jun 22 - Jun 23
Rustic Hideaway - Great Location + Pet Friendly!
A heated pool

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Haines City
8.8 out of 10, Excellent, (87 reviews)
"We had a small issue in the very beginning, but they were very accommodating and the communication was excellent! The house was perfect for what we needed it and we will definitely be renting again!"
United States
Kristina S.
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Exterior

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)
"The stay was great. There was a slight smell of a chemical odor but not overwhelming. The bed was comfy with clean sheets and there were enough clean towels. Made friends with the local cat. Overall, its was a great stay!"
United States
Marty H.
The price is ￥12,979
￥29,407 total
includes taxes & fees
Jun 20 - Jun 21
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Outdoor pool, a heated pool

🌿Welcome to the Jungle🌿

🌿Welcome to the Jungle🌿
Loughman
9.0 out of 10, Wonderful, (18 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 ￥27,081
￥80,101 total
includes taxes & fees
Jun 21 - Jun 22
🌿Welcome to the Jungle🌿
Villa, 4 Bedrooms | Exterior

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
8.0 out of 10, Very Good, (1 review)
"Loved the pool. Furniture serviceable not super comfy. Plan to bring in your own toilet paper, dish soap etc, they provide a very minimal amount of everything. "
United States
Michele
The price is ￥15,033
￥93,765 total
includes taxes & fees
Jun 20 - Jun 21
Sun Living: Golf Community, Private Pool 809 4 Bedroom Villa
House | 3 bedrooms, Internet

Family Villa w Lazy River Near Disney

Family Villa w Lazy River Near Disney
2.0 star property
Regal Palms
The price is ￥21,871
￥61,645 total
includes taxes & fees
Jun 27 - Jun 28
Family Villa w Lazy River Near Disney
Exterior

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, (29 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
The price is ￥11,970
￥37,706 total
includes taxes & fees
Jun 17 - Jun 18
Completely Renovated 3/2 Close to Disney parks
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

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews
501
Accommodation
10968 Villas
Lowest Price
￥27,042
Highest Price
￥143,160

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between ￥27,042 and ￥143,160 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.