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Winter Garden Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winter Garden holiday rentals

Interior

1. Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"The room was great, spacious, clean, just what we needed. All the amenities were as promised. We loved the stay."
United States
Ismael
The price is HK$549
HK$1,933 total
includes taxes & fees
1 Dec - 2 Dec
Upstay: Stylish 3BR Condo w Pationear Disney
A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

2. 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, (9 reviews)
"The house is absolutely beautiful! We stayed for two nights and had a wonderful experience. Communication with the host was excellent throughout our stay. We really enjoyed our time there and would definitely recommend this place!"
United States
isaac
The price is HK$1,430
HK$3,232 total
includes taxes & fees
1 Dec - 2 Dec
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Interior

3. FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.4 out of 10, Exceptional, (11 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
The price is HK$839
HK$1,486 total
includes taxes & fees
12 Nov - 13 Nov
FunTropicalTinyHomeGolfCartLake
Living area

4. 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$1,506 total
includes taxes & fees
6 Dec - 7 Dec
StylishAptWtrGrdnOppLake&Prk&Yrd
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

5. 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$917
HK$2,641 total
includes taxes & fees
11 Nov - 12 Nov
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

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

Cozy 1-bedroom with AC in awesome Winter Garden
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and had a great experience. Gina communicated with us right away, so we knew how to check in or had any questions answered. The property is very cute and looks new and was spotless. The location of the property is great as well. Downtown Winter Garden is adorable with great restaurants and is an easy drive down Plant St. It also was very convenient to where we were visiting in Ocoee and Orlando.We had everything we needed, highly recommend this property, and would stay there...
United States
Anonymous traveller
The price is HK$971
HK$2,709 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom with AC in awesome Winter Garden
Room

7. Modern 3BR Condo Near Disney- Pool and Hot Tub

Modern 3BR Condo Near Disney- Pool and Hot Tub
2.0 star property
Winter Garden
The price is HK$624
HK$1,851 total
includes taxes & fees
29 Nov - 30 Nov
Modern 3BR Condo Near Disney- Pool and Hot Tub
A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

8. 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
8 Nov - 9 Nov
Fire Pit & Yard: Updated Winter Garden Home!
Communal Outdoor Pool and Hot Tub

9. Upstay: Stylish 3BR Condo w Patio—near Disney

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
The price is HK$612
HK$2,162 total
includes taxes & fees
1 Dec - 2 Dec
Upstay: Stylish 3BR Condo w Patio—near Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

10. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
The price is HK$659
HK$2,057 total
includes taxes & fees
18 Nov - 19 Nov
Modern 3BR Resort Condo With Pool Near Disney
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

11. 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$3,756 total
includes taxes & fees
9 Nov - 10 Nov
Fire Pit & Yard: Updated Winter Garden Home!
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

12. 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)
"Super 2 bed 2 bath property walking distance to Winter Garden downtown area."
United States
Ron C.
House with large deck, walking distance to Historic Downtown Winter Garden
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

13. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is HK$643
HK$2,214 total
includes taxes & fees
9 Nov - 10 Nov
Winter Garden Family-friendly Condo w Resort Pool
A living room with a TV, a sofa, a coffee table, and a balcony with a view.

14. Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
The price is HK$596
HK$2,066 total
includes taxes & fees
18 Nov - 19 Nov
Upstay - Large Condo Near Disney w Pool and Gym
A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
The price is HK$675
HK$2,063 total
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 2BR Condo w Resort Pool & Sauna
A pool area with a waterfall feature, surrounded by tropical vegetation and a stone wall.

16. Studio Near Disney World Resort with Pools + more

Studio Near Disney World Resort with Pools + more
Kissimmee
The price is HK$1,241
HK$1,843 total
includes taxes & fees
6 Dec - 7 Dec
Studio Near Disney World Resort with Pools + more
Room

17. Upstay - Condo Near Disney w Pool Hot tub Sauna

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
The price is HK$687
HK$1,914 total
includes taxes & fees
30 Nov - 1 Dec
Upstay - Condo Near Disney w Pool Hot tub Sauna
Resort Amenities

18. Upstay 3BR Suite w Pool, Sauna & Games—Near Disney

Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Winter Garden
The price is HK$620
HK$2,093 total
includes taxes & fees
30 Nov - 1 Dec
Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

19. Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
The price is HK$643
HK$2,214 total
includes taxes & fees
9 Nov - 10 Nov
Upstay: 3BR Family Condo w Pool & Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

20. Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
The price is HK$596
HK$1,986 total
includes taxes & fees
18 Nov - 19 Nov
Condo With Sauna, Games, Poolnear 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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent
"Our room was really nice. Great bathroom and comfortable big bed. Walkable to stores and restaurants. Free really nice breakfast and close to Disney parks. We will stay here again."
Jean 1-night trip
Posted 2 hours ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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 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.