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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winter Garden condo rentals

Communal Outdoor Pool and Hot Tub

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

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
The price is ￥16,785
￥47,256 total
includes taxes & fees
Nov 10 - Nov 11
Upstay: Stylish 3BR Condo w Patio—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.

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
The price is ￥15,043
￥42,319 total
includes taxes & fees
Nov 17 - Nov 18
Family-Friendly 2BR Condo w Resort Pool & Sauna
Resort Amenities

3. Spacious Resort Suite w/ Pool & Sauna near Disney

Spacious Resort Suite w/ Pool & Sauna near Disney
Winter Garden
Spacious Resort Suite w/ Pool & Sauna near Disney
A poolside area with lounge chairs and a small table, surrounded by tropical plants and trees.

4. Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
Winter Garden
Upstay - 3BR Condo w Pool and Sauna
Resort Amenities

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

Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Winter Garden
The price is ￥11,718
￥41,347 total
includes taxes & fees
Nov 30 - Dec 1
Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.

6. Upstay Pet Friendly Condo 6 Minutes from Disney

Upstay Pet Friendly Condo 6 Minutes from Disney
Winter Garden
Upstay Pet Friendly Condo 6 Minutes from Disney
A balcony with a view of a natural landscape, a chair, and a table.

7. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
Winter Garden
Upstay Large Family Condo w Pool, Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

8. Upstay Pet-Friendly Condo with Pool

Upstay Pet-Friendly Condo with Pool
Winter Garden
The price is ￥13,460
￥43,483 total
includes taxes & fees
Nov 30 - Dec 1
Upstay Pet-Friendly Condo with Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

9. Upstay - LRG Condo w Outdoor Pool, Sauna

Upstay - LRG Condo w Outdoor Pool, Sauna
Winter Garden
The price is ￥16,310
￥47,510 total
includes taxes & fees
Nov 17 - Nov 18
Upstay - LRG Condo w Outdoor Pool, Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

10. Family Condo Near Disney w Pool & Gym—Pets Welcome

Family Condo Near Disney w Pool & Gym—Pets Welcome
Winter Garden
The price is ￥13,460
￥43,483 total
includes taxes & fees
Nov 30 - Dec 1
Family Condo Near Disney w Pool & Gym—Pets Welcome
A spacious living room with a sofa, a coffee table, and a TV. There are large windows with curtains, a balcony, and a ceiling fan.

11. Modern Pet-Friendly 2BR Condo—6 mins from Disney

Modern Pet-Friendly 2BR Condo—6 mins from Disney
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"I was very impressed pictures did no justice, it was extremely clean, host was friendly and easy to access."
United States
Tay T.
The price is ￥16,943
￥43,842 total
includes taxes & fees
Nov 18 - Nov 19
Modern Pet-Friendly 2BR Condo—6 mins from Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

12. 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 ￥15,360
￥46,115 total
includes taxes & fees
Dec 2 - Dec 3
Upstay - Condo w Pool and More - Near Disney
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.

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

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
The price is ￥12,035
￥41,707 total
includes taxes & fees
Nov 18 - Nov 19
Upstay - Large Condo Near Disney w Pool and Gym
A modern living room with a sofa, armchairs, a coffee table, and a TV. There is a balcony with a view of trees and a railing.

14. Modern Condo with Private Balcony Near Disney

Modern Condo with Private Balcony Near Disney
Winter Garden
The price is ￥11,718
￥41,347 total
includes taxes & fees
Nov 30 - Dec 1
Modern Condo with Private Balcony Near Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

15. Modern 3BR Resort Condo with Pool near Disney

Modern 3BR Resort Condo with Pool near Disney
Winter Garden
The price is ￥12,985
￥42,943 total
includes taxes & fees
Nov 18 - Nov 19
Modern 3BR Resort Condo with Pool near Disney
Stunning Aerial View Of The Property Surrounded By Nature

16. Family-friendly Condo w/ Pool & Sauna—near Disney

Family-friendly Condo w/ Pool & Sauna—near Disney
Winter Garden
Family-friendly Condo w/ Pool & Sauna—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.

17. 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)
Upstay Disney Pet Friendly Condo w Pool Spa Games
Resort Amenities

18. Upstay: Pet-Friendly Family Condo w Pool—Sleeps 8

Upstay: Pet-Friendly Family Condo w Pool—Sleeps 8
Winter Garden
The price is ￥13,935
￥44,655 total
includes taxes & fees
Nov 17 - Nov 18
Upstay: Pet-Friendly Family Condo w Pool—Sleeps 8
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 ￥12,985
￥44,685 total
includes taxes & fees
Nov 9 - Nov 10
Upstay: 3BR 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.

20. Upstay Modern Condo w Pool—10 minutes to Disney

Upstay Modern Condo w Pool—10 minutes to Disney
Winter Garden
Upstay Modern Condo w Pool—10 minutes to 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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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
A brick building with a clock tower and a sign that reads "Winter Garden."

Frequently Asked Questions

Why book your condo in Winter Garden with Expedia?

Reserving a condo in Winter Garden is as simple as clicking on your travel dates and choosing a place that suits your style. Seeking something upscale or budget friendly, or a property that also comes with a kitchen and laundry? Use Expedia's search filters to further narrow your search results and find the ideal fit.

How can I find cheap condos in Winter Garden?

The easiest way to compare cheap condos in Winter Garden is with Expedia's filter tool. Narrow down your search by amenities, star rating and budget to take advantage of awesome prices in just a few keystrokes.

What is there to do in Winter Garden near my condo?

There are tons of terrific things to see and do in Winter Garden. You won't want to miss leading attractions like Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail. Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve are other must-see's.