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Winter Garden Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
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 vacation rentals

Pool

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 AED 382
AED 749 total
includes taxes & fees
2 Sep - 3 Sep
StylishAptWtrGrdnOppLake&Prk&Yrd
2 bedrooms, WiFi, bed sheets

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 AED 566
AED 1,843 total
includes taxes & fees
6 Sep - 7 Sep
Fire Pit & Yard: Updated Winter Garden Home!
House (2 Bedrooms) | Interior

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is AED 731
AED 1,833 total
includes taxes & fees
6 Sep - 7 Sep
Fire Pit & Yard: Updated Winter Garden Home!
Coffee/tea maker, fridge, microwave, oven

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.
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Coffee/tea maker, fridge, microwave, oven

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
The price is AED 298
AED 904 total
includes taxes & fees
28 Aug - 29 Aug
Relaxing retreat w/ pool & BBQ grill
Interior

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 AED 441
AED 815 total
includes taxes & fees
31 Aug - 1 Sep
FunTropicalTinyHomeGolfCartLake
Interior

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 AED 559
AED 1,170 total
includes taxes & fees
6 Sep - 7 Sep
House with large deck, walking distance to Historic Downtown Winter Garden
Interior

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 traveler
The price is AED 595
AED 1,500 total
includes taxes & fees
23 Sep - 24 Sep
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Outdoor pool

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 AED 661
AED 1,072 total
includes taxes & fees
30 Aug - 31 Aug
The Oak View Place..
Pool

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.
The price is AED 1,201
AED 2,134 total
includes taxes & fees
30 Aug - 31 Aug
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Apartment (3 Bedrooms) | Interior

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 AED 242
AED 888 total
includes taxes & fees
31 Aug - 1 Sep
Upstay: Condo Near Disney w Pool, Sauna
Private kitchen

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 AED 997
AED 2,430 total
includes taxes & fees
28 Aug - 29 Aug
Welcoming clean 3-bedroom house in cozy neighborhood in Oakland FL
House | 3 bedrooms, high-speed internet

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 AED 422
AED 1,121 total
includes taxes & fees
9 Sep - 10 Sep
Upstay 3BR Condo w Pool Patio Near Disney
Interior

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
Property grounds

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
The price is AED 275
AED 957 total
includes taxes & fees
30 Aug - 31 Aug
Upstay - Pet-Friendly Condo - Sauna, Pool
A heated pool

16. Studio Near Disney World

Studio Near Disney World
Kissimmee
Studio Near Disney World
A heated pool

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is AED 489
AED 789 total
includes taxes & fees
28 Aug - 29 Aug
1-Bedroom Villa Near Disney w/ Pool & Lazy River
Exterior

18. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is AED 257
AED 1,031 total
includes taxes & fees
30 Aug - 31 Aug
Winter Garden Family-friendly Condo w Resort Pool
Apartment (3 Bedrooms) | Interior

19. Spacious 3BR Family Getaway w Pool Near Disney

Spacious 3BR Family Getaway w Pool Near Disney
4.0 star property
Winter Garden
Spacious 3BR Family Getaway w Pool Near Disney
Interior

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.
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Bed was awesome and shower great, breakfast great!"
Greg 1-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Frequently asked questions

Can I find a vacation rental in Winter Garden?

Yes, we offer vacation rentals in Winter Garden close to Winter Garden Art Association, or you can go with a more remote option if you'd like a relaxing place to 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's the top vacation rental that Winter Garden has to offer?

Formosa Valley Resort by UNE Homes: This vacation home near 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 vacation rentals are there in Winter Garden?

With 7 Expedia vacation rentals, you're sure 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 vacation rentals like in Winter Garden?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Winter Garden. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.