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Winter Garden Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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 ￥16,577
￥32,516 total
includes taxes & fees
Aug 16 - Aug 17
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)
"One of best VRBO’s we have stayed. Very well set up and very warm and comfortable. Felt like home. And the location is perfect. We will be back. "
United States
John T.
The price is ￥24,558
￥80,492 total
includes taxes & fees
Aug 23 - Aug 24
Fire Pit & Yard: Updated Winter Garden Home!
Coffee/tea maker, fridge, microwave, oven

3. 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 ￥17,820
￥55,133 total
includes taxes & fees
Sep 7 - Sep 8
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Coffee/tea maker, fridge, microwave, oven

4. 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 ￥12,917
￥39,091 total
includes taxes & fees
Aug 15 - Aug 16
Relaxing retreat w/ pool & BBQ grill
House (2 Bedrooms) | Interior

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥31,719
￥79,555 total
includes taxes & fees
Aug 24 - Aug 25
Fire Pit & Yard: Updated Winter Garden Home!
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 ￥19,127
￥35,704 total
includes taxes & fees
Aug 23 - Aug 24
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, (25 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 ￥32,850
￥60,847 total
includes taxes & fees
Sep 12 - Sep 13
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 ￥27,987
￥67,845 total
includes taxes & fees
Sep 13 - Sep 14
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
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 ￥42,876
￥80,752 total
includes taxes & fees
Sep 8 - Sep 9
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Outdoor pool

10. 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 ￥28,690
￥46,502 total
includes taxes & fees
Aug 16 - Aug 17
The Oak View Place..
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 ￥12,308
￥40,565 total
includes taxes & fees
Sep 2 - Sep 3
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 ￥43,125
￥104,181 total
includes taxes & fees
Sep 12 - Sep 13
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 ￥12,609
￥42,240 total
includes taxes & fees
Aug 17 - Aug 18
Upstay 3BR Condo w Pool Patio Near Disney
Coffee/tea maker, microwave, oven, stovetop

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

Grace Suite in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
The price is ￥42,238
￥86,948 total
includes taxes & fees
Aug 31 - Sep 1
Grace Suite in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Interior

15. 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.
The price is ￥87,709
￥177,073 total
includes taxes & fees
Aug 31 - Sep 1
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Lobby

16. 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 ￥14,496
￥44,905 total
includes taxes & fees
Aug 27 - Aug 28
Upstay Disney Pet Friendly Condo w Pool Spa Games
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 ￥24,520
￥36,993 total
includes taxes & fees
Sep 14 - Sep 15
1-Bedroom Villa Near Disney w/ Pool & Lazy River
A heated pool

18. Studio Near Disney World

Studio Near Disney World
Kissimmee
The price is ￥17,210
￥28,770 total
includes taxes & fees
Sep 14 - Sep 15
Studio Near Disney World
Exterior

19. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is ￥11,157
￥44,720 total
includes taxes & fees
Aug 17 - Aug 18
Winter Garden Family-friendly Condo w Resort Pool
Apartment (3 Bedrooms) | Interior

20. 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 ￥12,911
￥41,243 total
includes taxes & fees
Aug 17 - Aug 18
Spacious 3BR Family Getaway w Pool 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
"Fun time"
Christopher 3-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

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 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.