A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Winter Garden Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Winter Garden vacation rentals

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
Fire Pit & Yard: Updated Winter Garden Home!

2. Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
8.0 out of 10, Very good, (1 review)
"The condo was perfect for our blended family. We enjoyed the space, including the balcony overseeing the pool. My kids enjoyed the game room. Host was friendly/responsive. Was able to work through an unexpected challenge and find reasonable solution. The condo has definitely been well used and could use some updating. I can send a list to host if requested. Overall we had a great stay, conveniently located to stores/restaurants. Had most of the basic supplies needed."
United States
Andrea Nicole
Upstay Condo w Pool Sauna Sleeps 8
A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

3. Upstay Modern Condo w Pool10 Minutes to Disney

Upstay Modern Condo w Pool10 Minutes to Disney
3.5 star property
Winter Garden
Upstay Modern Condo w Pool10 Minutes to Disney

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

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
Upstay - Condo Near Disney w Pool Hot tub Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

5. Near Disney - Family Condo w Pool, Games, and More

Near Disney - Family Condo w Pool, Games, and More
3.0 star property
Winter Garden
6.0 out of 10, (1 review)
"You get what you pay for for sure! This was a place to stay that was clean inside, just very outdated and the hall smell was SO HORRIBLE. They have fragrance machines throughout the halls to where you can literally taste the fragrance. It was going into our room and we all felt nauseous because of how strong it was. I also would like to recommend the place gets carts so guests can easily transfer their belongings from the parking garage to their room because it was a FAR walk with all of our...
United States
Aubree
Near Disney - Family Condo w Pool, Games, and More

6. Upstay - Condo w Hot Tub and Pool - Near Disney

Upstay - Condo w Hot Tub and Pool - Near Disney
2.0 star property
Winter Garden
Upstay - Condo w Hot Tub and Pool - Near Disney
A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

7. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
The price is P3,936
P14,900 total
includes taxes & fees
Oct 21 - Oct 22
Upstay Large Family Condo w Pool, Sauna

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

Modern 3BR Condo Near Disney- Pool and Hot Tub
2.0 star property
Winter Garden
Modern 3BR Condo Near Disney- Pool and Hot Tub

9. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
3.0 star property
Winter Garden
Upstay Condo Near Disney w Pool & Sauna

10. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
2.0 star property
Winter Garden
Upstay Tropical Style Family Condo w Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

11. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
Modern 3BR Resort Condo With Pool Near Disney
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.

12. Upstay - Condo Near Disney w Pool-spa-sauna-games

Upstay - Condo Near Disney w Pool-spa-sauna-games
2.0 star property
Winter Garden
The price is P4,775
P14,892 total
includes taxes & fees
Sep 30 - Oct 1
Upstay - Condo Near Disney w Pool-spa-sauna-games

13. Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
2.0 star property
Winter Garden
Upstay Stylish 3BR Condo w Patio Near Disney

14. 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 P8,220
P20,244 total
includes taxes & fees
Oct 10 - Oct 11
Upstay 3BR Condo w Pool Patio Near Disney

15. Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
2.0 star property
Winter Garden
The price is P9,044
P18,818 total
includes taxes & fees
Oct 10 - Oct 11
Upstay - Modern Family Apartment w Pool Hot Tub
A laundry area with a washing machine, dryer, and a wall-mounted decorative piece.

16. Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
2.0 star property
Winter Garden
Upstay Large Family Condo w Pool Sauna
A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

17. Upstay: Condo Near Disney w Games, Pool

Upstay: Condo Near Disney w Games, Pool
3.5 star property
Winter Garden
Upstay: Condo Near Disney w Games, Pool

18. 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 P4,436
P15,463 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Condo Near Disney w Pool, Sauna

19. Upstay - Condo w Pool - Near Disney!

Upstay - Condo w Pool - Near Disney!
3.5 star property
Winter Garden
Upstay - Condo w Pool - Near Disney!
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.

20. Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
4.0 star property
Winter Garden
The price is P4,873
P14,549 total
includes taxes & fees
Sep 28 - Sep 29
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Overall, The Grove is a really nice place to stay. I wish they had shuttles to all the parks unfortunately they do not.,"
Kayla 6-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

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 Surfari Water Park, 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: You might like this vacation home rental near Winter Garden. It 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 6 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.