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Winter Garden Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winter Garden holiday rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (23 reviews)
"Great place to stay! "
United States
Lindsey W.
The price is HK$815
HK$1,599 total
includes taxes & fees
2 Sept - 3 Sept
StylishAptWtrGrdnOppLake&Prk&Yrd
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

2. 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$1,207
HK$3,933 total
includes taxes & fees
6 Sept - 7 Sept
Fire Pit & Yard: Updated Winter Garden Home!
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is HK$1,560
HK$3,912 total
includes taxes & fees
7 Sept - 8 Sept
Fire Pit & Yard: Updated Winter Garden Home!
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

4. 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, (23 reviews)
"The place was exceptional for our time in winter garden. "
United States
Steve S.
The price is HK$829
HK$2,643 total
includes taxes & fees
27 Sept - 28 Sept
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
A modern kitchen with a wooden island, white cabinetry, and a built-in microwave.

5. Relaxing retreat w/ pool & BBQ grill

Relaxing retreat w/ pool & BBQ grill
Winter Garden
2.0 out of 10, (2 reviews)
"If you like camping in a tent with campfires to cook and cold water to shower, then THIS is the place for you! Hot water was in short supply, Air Conditioning broke down, the oven did not work (this was the number one reason we chose this place), we saw cockroaches in the kitchen, no handle on the entry door, no hand towels, one washcloth, neighbors are 5 feet away and LOVE to blast their radios early in the morning and late at night, sheets are scratchy, and the refrigerator leaked and...
United States
Peter
Relaxing retreat w/ pool & BBQ grill

6. 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.
The price is HK$964
HK$1,782 total
includes taxes & fees
25 Sept - 26 Sept
FunTropicalTinyHomeGolfCartLake
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

7. 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, (27 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$1,192
HK$2,498 total
includes taxes & fees
6 Sept - 7 Sept
House with large deck, walking distance to Historic Downtown Winter Garden
A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

8. 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$1,270
HK$3,200 total
includes taxes & fees
11 Sept - 12 Sept
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
A swimming pool with a stone deck, a dog nearby, and a view of a residential area with houses and trees.

9. 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$1,411
HK$2,287 total
includes taxes & fees
30 Aug - 31 Aug
The Oak View Place..
A wooden deck with a hot tub, a wooden dock extending into a body of water, and a view of the water and sky.

10. 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.
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

11. 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$1,922 total
includes taxes & fees
2 Sept - 3 Sept
Upstay: Condo Near Disney w Pool, Sauna
A kitchen with a central island, bar stools, a refrigerator, and a microwave.

12. Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL

Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
Killarney
The price is HK$2,128
HK$5,186 total
includes taxes & fees
28 Aug - 29 Aug
Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL

13. Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney
2.0 star property
Winter Garden
The price is HK$901
HK$2,393 total
includes taxes & fees
9 Sept - 10 Sept
Upstay 3BR Condo w Pool Patio Near Disney

14. Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
10.0 out of 10, Exceptional, (1 review)
"We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with...
United States
Kristen R.
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
A balcony with a ceiling fan, a white cushioned chair, a small table, and a potted plant.

15. Upstay - Pet-Friendly Condo - Sauna, Pool

Upstay - Pet-Friendly Condo - Sauna, Pool
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"Very clean and spacious great location. Would definitely come back "
United States
KELLEE
Upstay - Pet-Friendly Condo - Sauna, Pool

16. Studio Near Disney World

Studio Near Disney World
Kissimmee
The price is HK$1,152
HK$1,814 total
includes taxes & fees
25 Sept - 26 Sept
Studio Near Disney World

17. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is HK$1,434
HK$2,162 total
includes taxes & fees
25 Sept - 26 Sept
1-Bedroom Villa Near Disney w/ Pool & Lazy River

18. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
Winter Garden Family-friendly Condo w Resort Pool

19. Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
4.0 star property
Winter Garden
The price is HK$635
HK$2,028 total
includes taxes & fees
30 Aug - 31 Aug
Spacious 3BR Family Getaway w Pool Near Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

20. 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.
The price is HK$619
HK$2,287 total
includes taxes & fees
31 Aug - 1 Sept
Upstay - Condo w Pool and More - Near 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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"I have been there more than 5 times, and still love this resort. The only i thing they should get a little better is the food, maybe more variety and incrase the quality of food, but everything else, its awesome !!!! My son love it !!!!"
Carlos 2-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

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 Winter Garden Art Association, 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 7 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.