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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Featured Villas in Winter Garden and around

Interior
Regal Palms Swanky

Regal Palms Swanky

4.0 star property
Regal Palms
The price is €257
includes taxes & fees
15 Nov - 16 Nov
Regal Palms Swanky
Villa, 3 Bedrooms | Aerial view
Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa

Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa

3.0 star property
Kissimmee
The price is €440
includes taxes & fees
11 Nov - 12 Nov
Surfstyle At Margaritaville By Shine Villas 022 3 Bedroom Villa
Outdoor dining
Banana Leaf Villa- Book your gathering today!

Banana Leaf Villa- Book your gathering today!

2.0 star property
Orlovista
8.0 out of 10, Very good, (3)
"The property looks nice in pictures, but in reality this is (or recently was) an assisted living facility and I think they just rent out spare bedrooms. The property was probably nice once upon a time, but in its current state it is pretty run down and not very well maintained. I saw people working at the desk maybe 2 times during my stay. No welcome or response to phone calls. The walls were painted haphazardly. No control of temperature as the thermostats are in the halls with locks and set to...
United States
Joseph
The price is €94
includes taxes & fees
11 Nov - 12 Nov
Banana Leaf Villa- Book your gathering today!
Front of property
681-Sticks

681-Sticks

2.0 star property
Kissimmee
681-Sticks
Exterior
Top 1% College Park GuestHouse Villa/Oasis - Mins to DT ORL/Winter Park & Eola

Top 1% College Park GuestHouse Villa/Oasis - Mins to DT ORL/Winter Park & Eola

College Park
10.0 out of 10, Exceptional, (26)
"My wife bought me tickets to see the Daytona 500. This start was about 45 minutes from the track and for the value, the absolute best option for us. The hosts are top notch and went above and beyond to make our stay the best! They are some of the most generous host we have ever stayed at. I'm a bigger guy, so outside of the small shower, everything was perfect!!"
United States
Kirk N.
The price is €180
includes taxes & fees
11 Nov - 12 Nov
Top 1% College Park GuestHouse Villa/Oasis - Mins to DT ORL/Winter Park & Eola
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, (21)
"Good deal"
United States
Jorge C.
The price is €211
includes taxes & fees
12 Nov - 13 Nov
Completely Renovated 3/2 Close to Disney parks
Exterior
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911

Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911

Orlando
Last Minute Disney Getaway! Luxury Villa with Private patio. Book Now! #115911
Exterior
Stunning lake view, private pool,near Disney ,games room,free WiFi ,play golf

Stunning lake view, private pool,near Disney ,games room,free WiFi ,play golf

Kissimmee
9.2 out of 10, Wonderful, (248)
"This was a beautiful house with so much space. It was so clean, we felt like we were the first people to stay here. The pool and pool area was so relaxing. It was quiet. The beds and bedding were really comfortable. We will definitely stay here again!"
United States
Nicole S.
The price is €232
includes taxes & fees
13 Nov - 14 Nov
Stunning lake view, private pool,near Disney ,games room,free WiFi ,play golf
A heated pool
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, (9)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is €438
includes taxes & fees
11 Nov - 12 Nov
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior
Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Pet Friendly, Modern Tiny Home in Vibrant Clermont!

Clermont
10.0 out of 10, Exceptional, (12)
"Very cool place, extremely neat and clean and much more comfortable than an RV."
United States
brian d.
The price is €234
includes taxes & fees
30 Nov - 1 Dec
Pet Friendly, Modern Tiny Home in Vibrant Clermont!
Exterior
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Altamonte Springs
9.0 out of 10, Wonderful, (2)
"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.
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Villa, 5 Bedrooms | Exterior
5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa

5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa

3.0 star property
Solterra Resort
The price is €591
includes taxes & fees
23 Nov - 24 Nov
5 Bed Bliss At Solterra By Shine Villas 121 5 Bedroom Villa
Exterior
Resort style family friendly vacation villa

Resort style family friendly vacation villa

Orlando
8.8 out of 10, Excellent, (11)
"Quiet location. There were spots on the stair carpeting, lightbulbs were out, suppose to accommodate 8 but not enough silverware for eight people. Beds were very uncomfortable "
United States
Lynn
Resort style family friendly vacation villa
Exterior
Fully-Equipped Villa Next to Disney!

Fully-Equipped Villa Next to Disney!

Kissimmee
9.4 out of 10, Exceptional, (74)
"It was clean and centrally located to the disney parks "
United States
Angela S.
Fully-Equipped Villa Next to Disney!
Indoor pool
7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!

7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!

Edgewood
9.4 out of 10, Exceptional, (19)
"The host did not allow for a later check out, which was a bit of a hassle."
United States
Carlos Eduardo de O.
7BR Lakefront Duplex w/ Pool, Sauna & Hot Tub!
Pool
5BR Heated Pool & Grill w/ Pool Table & Darts!

5BR Heated Pool & Grill w/ Pool Table & Darts!

Sandy Ridge
10.0 out of 10, Exceptional, (3)
"Family of 4 golf trip to FLA and we wanted a central location near Orlando/DisneyWorld with a pool. This place totally fit the bill! Nice and clean, owner was great with communication and any of our questions, the property matched all the details of the listing. Would highly recommend for anyone looking for a nice place to stay and also chill out around a heated pool!"
Canada
Chris F.
5BR Heated Pool & Grill w/ Pool Table & Darts!
Outdoor pool, a heated pool
Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool

Sandy Ridge
9.2 out of 10, Wonderful, (9)
"The house was beautiful and clean. The beds were comfortable. I would stay there again if I’m ever in the area."
United States
Carla R.
Gorgeous VILLA near Disney, Private Heated South Pool
Pool
2816 Simile · Storey Lake•10BR•Fire Pit•Pool•Hot Tub•Game•EVChrg

2816 Simile · Storey Lake•10BR•Fire Pit•Pool•Hot Tub•Game•EVChrg

Kissimmee
10.0 out of 10, Exceptional, (23)
"We had a fantastic experience, everything was as described to the T. We take this trip every year and this location was one of our best. "
United States
Heidi E.
2816 Simile · Storey Lake•10BR•Fire Pit•Pool•Hot Tub•Game•EVChrg
Exterior
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
8.8 out of 10, Excellent, (83)
"Great location to parks. House was perfect in accommodating 14 family members with 7 bedrooms. Pool was fantastic and nicely heated. Would stay again."
United States
Janet E.
Beautiful 7 Bedroom Villa - 4 King Suites, 5.5 Bath, Sleeps 16!
Exterior
Close to Disney - shabby chic style villa with private pool!!

Close to Disney - shabby chic style villa with private pool!!

Lake Berkley
9.4 out of 10, Exceptional, (120)
"Very good villa; very comfortable beds and in a great location on the 192, close to shops, parks and restaurants."
United Kingdom
Ann Q.
The price is €369
includes taxes & fees
11 Nov - 12 Nov
Close to Disney - shabby chic style villa with private pool!!
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

CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

10/10 Excellent
"The resort and grounds were very nice. Lush landscaping, beautiful decor. Both pool areas are great! I really loved the deck of the water park and pool area, it’s a rubber type turf, it’s non slip but also nice on the feet. "
Ruth 2-night trip
Posted 11 hours ago
CoCo Key Hotel and Water Resort 

Find out more about Winter Garden

Winter Garden Villas information

Number of reviews
592
Accommodation
10415 Villas
Lowest Price
€94
Highest Price
€591

Frequently asked questions

How much do villas in Winter Garden cost?
Villas in Winter Garden cost between €94 and €591 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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