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Winter Garden Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winter Garden holiday rentals

2 bedrooms, WiFi, bed sheets

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
"Amazing House! Would stay again anytime!"
United States
Patrick O.
The price is HK$1,208
HK$3,913 total
includes taxes & fees
27 Sept - 28 Sept
Fire Pit & Yard: Updated Winter Garden Home!
Pool

2. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Lindsey W.
The price is HK$816
HK$1,585 total
includes taxes & fees
21 Oct - 22 Oct
StylishAptWtrGrdnOppLake&Prk&Yrd
Interior

3. House with large deck, walking distance to Historic Downtown Winter Garden

House with large deck, walking distance to Historic Downtown Winter Garden
Winter Garden
9.8 out of 10, Exceptional, (29 reviews)
"If you need a nice place to stay in downtown Winter Garden, please consider this place. It is the perfect size for a party of 4 and it is conveniently located to downtown restaurant’s. We stayed 8 nights and could not have been happier."
United States
Sam M.
The price is HK$1,617
HK$3,008 total
includes taxes & fees
29 Sept - 30 Sept
House with large deck, walking distance to Historic Downtown Winter Garden
Interior

4. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is HK$1,561
HK$3,916 total
includes taxes & fees
27 Sept - 28 Sept
Fire Pit & Yard: Updated Winter Garden Home!
Interior

5. FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.2 out of 10, Wonderful, (10 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
FunTropicalTinyHomeGolfCartLake
Coffee/tea maker, fridge, microwave, oven

6. Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Winter Garden
9.8 out of 10, Exceptional, (24 reviews)
"The property was perfect for our week with family"
United States
Steve S.
The price is HK$838
HK$2,638 total
includes taxes & fees
21 Oct - 22 Oct
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Interior

7. Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Winter Garden
10.0 out of 10, Exceptional, (8 reviews)
"Place was clean and excellent location and club amenities "
United States
Anonymous traveller
The price is HK$1,271
HK$3,163 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Interior

8. Cozy 1-bedroom with AC in awesome Winter Garden

Cozy 1-bedroom with AC in awesome Winter Garden
Winter Garden
Cozy 1-bedroom with AC in awesome Winter Garden
Pool

9. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (34 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
The price is HK$2,463
HK$4,301 total
includes taxes & fees
4 Oct - 5 Oct
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
TV, table football, computer monitors

10. Luxury Retreat, Close to Disney

Luxury Retreat, Close to Disney
Winter Garden
The price is HK$1,807
HK$3,125 total
includes taxes & fees
24 Sept - 25 Sept
Luxury Retreat, Close to Disney
Outdoor pool

11. The Oak View Place..

The Oak View Place..
Oakland
9.2 out of 10, Wonderful, (10 reviews)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
The price is HK$1,412
HK$2,265 total
includes taxes & fees
21 Sept - 22 Sept
The Oak View Place..
Interior

12. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"The unit was very clean and organized when we arrived. All the amenities and appliances that come with the unit worked amazing. The only exception was the WiFi. It was a bit slow, however this could be easily fixed and should not discourage from booking this property. Being at the pool was the highlight of staying at this property. It was clean and came with fun pool sized amenities like pool basketball and connect 4. Being in the lobby was also fun with the ping pong table and pool table. The...
United States
Nancy
The price is HK$541
HK$1,924 total
includes taxes & fees
21 Sept - 22 Sept
Upstay: Condo Near Disney w Pool, Sauna
3 bedrooms, Internet

13. Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
2.0 star property
Winter Garden
The price is HK$592
HK$2,047 total
includes taxes & fees
4 Oct - 5 Oct
Upstay Stylish 3BR Condo w Patio Near Disney
Exterior

14. Family Fun Condo Pool and Sauna near Disney

Family Fun Condo Pool and Sauna near Disney
Winter Garden
9.6 out of 10, Exceptional, (5 reviews)
"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "
United States
John and Dawn R.
Family Fun Condo Pool and Sauna near Disney
A heated pool

15. Studio Near Disney World Resort with Pools + more

Studio Near Disney World Resort with Pools + more
Kissimmee
The price is HK$1,059
HK$1,701 total
includes taxes & fees
23 Sept - 24 Sept
Studio Near Disney World Resort with Pools + more
A heated pool

16. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is HK$1,263
HK$1,939 total
includes taxes & fees
24 Sept - 25 Sept
1-Bedroom Villa Near Disney w/ Pool & Lazy River
Exterior

17. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is HK$494
HK$2,100 total
includes taxes & fees
21 Sept - 22 Sept
Winter Garden Family-friendly Condo w Resort Pool
Interior

18. Upstay - Condo w Pool and More - Near Disney

Upstay - Condo w Pool and More - Near Disney
Winter Garden
9.0 out of 10, Wonderful, (22 reviews)
"Great place! Convenient, cozy and clean!"
United States
SHARLA B.
Upstay - Condo w Pool and More - Near Disney
Lobby

19. Family-Friendly 2BR Condo w Resort Pool & Sauna

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
The price is HK$549
HK$1,976 total
includes taxes & fees
21 Sept - 22 Sept
Family-Friendly 2BR Condo w Resort Pool & Sauna
Lobby

20. Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
Winter Garden
10.0 out of 10, Exceptional, (1 review)
The price is HK$533
HK$1,958 total
includes taxes & fees
21 Sept - 22 Sept
Upstay Disney Pet Friendly Condo w Pool Spa Games
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Cleanliness and well taken care. Easy assess around the campus"
Larry 2-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Winter Garden

Search for holiday rentals in Winter Garden on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Garden using one of the methods below:

  • View our selection of featured holiday rentals in Winter Garden
  • Use the map to find apartments and other holiday homes in the Winter Garden neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Garden while they last

Look no further and take a look at our great range of rental properties in Winter Garden!

Frequently asked questions

Can I find a holiday rental in Winter Garden?

Yes, there are holiday rentals in Winter Garden close to Surfari Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Winter Garden speak highly of the fun-filled theme parks and array of shops. While you're here, grab a bite or have a drink at the top-notch restaurants.

What are some of the best holiday rentals that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes: This holiday home rental outside of Winter Garden is equipped with an outdoor pool, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Winter Garden?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Winter Garden stay.

What can I see and do in Winter Garden?

Family-friendly attractions include Surfari Water Park and Central Florida Railroad Museum, whereas Lake Louisa State Park and West Orange Trail are a couple of great spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are holiday rentals like in Winter Garden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Garden. Holiday rentals feature amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.