Search and Rent Winter Garden Condos

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Our top choices for Winter Garden condo rentals

Family Fun Condo: Pool, Sauna—near Disney

Family Fun Condo: Pool, Sauna—near Disney
Winter Garden
$212 nightly
The price is $238
Dec 16 - Dec 17
Total with taxes and fees
Family Fun Condo: Pool, Sauna—near Disney

Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$261 nightly
The price is $293
Jan 12 - Jan 13, 2026
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym

Modern 3BR Resort Condo w/ Pool near Disney World

Modern 3BR Resort Condo w/ Pool near Disney World
2.5 star property
Winter Garden
$239 nightly
The price is $267
Dec 16 - Dec 17
Total with taxes and fees
Modern 3BR Resort Condo w/ Pool near Disney World

Upstay: 3BR Condo w Pool, Sauna—Near Disney

Upstay: 3BR Condo w Pool, Sauna—Near Disney
Winter Garden
$259 nightly
The price is $291
Jan 12 - Jan 13, 2026
Total with taxes and fees
Upstay: 3BR Condo w Pool, Sauna—Near Disney

Upstay Pet-friendly Condo with Pool near Disney

Upstay Pet-friendly Condo with Pool near Disney
Winter Garden
"Super convenient if your family is looking for an affordable way to visit your college student participating in the Disney College program. Helped that it was pet friendly."
United States
Jennifer A.
$236 nightly
The price is $264
Dec 17 - Dec 18
Total with taxes and fees
Upstay Pet-friendly Condo with Pool near Disney

Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
Winter Garden
$236 nightly
The price is $264
Dec 16 - Dec 17
Total with taxes and fees
Upstay - 3BR Condo w Pool and Sauna

Upstay: Modern & Sunny 2BR Condo Near Disney

Upstay: Modern & Sunny 2BR Condo Near Disney
Winter Garden
$213 nightly
The price is $239
Dec 17 - Dec 18
Total with taxes and fees
Upstay: Modern & Sunny 2BR Condo Near Disney

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
$217 nightly
The price is $244
Dec 18 - Dec 19
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna

Pet-friendly Condo Pool, Sauna—Near Disney

Pet-friendly Condo Pool, Sauna—Near Disney
Winter Garden
$257 nightly
The price is $289
Jan 12 - Jan 13, 2026
Total with taxes and fees
Pet-friendly Condo Pool, Sauna—Near Disney

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
Winter Garden
$236 nightly
The price is $264
Dec 16 - Dec 17
Total with taxes and fees
Upstay: Condo Near Disney w Pool, Sauna

Upstay Bright 3BR Condo w Pool & Patio—near Disney

Upstay Bright 3BR Condo w Pool & Patio—near Disney
Winter Garden
$236 nightly
The price is $264
Dec 16 - Dec 17
Total with taxes and fees
Upstay Bright 3BR Condo w Pool & Patio—near Disney

Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
Winter Garden
$236 nightly
The price is $264
Dec 16 - Dec 17
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna

Upstay - Condo Near Disney w Pool-Spa-Sauna-Games

Upstay - Condo Near Disney w Pool-Spa-Sauna-Games
Winter Garden
$211 nightly
The price is $237
Dec 17 - Dec 18
Total with taxes and fees
Upstay - Condo Near Disney w Pool-Spa-Sauna-Games

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

Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Winter Garden
$240 nightly
The price is $269
Dec 18 - Dec 19
Total with taxes and fees
Upstay 3BR Suite w Pool, Sauna & Games—Near Disney

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1)
"we had a wonderful stay at Palisades resort on 4th floor (top floor) . Condo was very spacious/clean and close to Disney amd rte 192. 2 very large bedrooms (with own bathrooms ) kitchen/living room/dining area in between, great for privacy. huge screened in patio, with views of nightly disney fireworks exterior of bldg could have been kept up better. trash/garbage visible as you pull into parking garage, and very messy/scattered around. other than that, property was great and would stay there...
United States
Kristi F.
$217 nightly
The price is $244
Dec 18 - Dec 19
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
2.5 star property
Winter Garden
$234 nightly
The price is $263
Jan 12 - Jan 13, 2026
Total with taxes and fees
Upstay: 3BR Family Condo w Pool & Sauna

Upstay Pet-Friendly Condo with Pool

Upstay Pet-Friendly Condo with Pool
Winter Garden
$262 nightly
The price is $294
Jan 12 - Jan 13, 2026
Total with taxes and fees
Upstay Pet-Friendly Condo with Pool

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
$212 nightly
The price is $238
Dec 16 - Dec 17
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna

Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Family Condo near Disney
Winter Garden
$275 nightly
The price is $308
Jan 8 - Jan 9, 2026
Total with taxes and fees
Upstay - Pet-Friendly Family Condo near Disney

Upstay - Pet-Friendly Condo - Sauna, Pool

Upstay - Pet-Friendly Condo - Sauna, Pool
Winter Garden
$217 nightly
The price is $244
Jan 7 - Jan 8, 2026
Total with taxes and fees
Upstay - Pet-Friendly Condo - Sauna, Pool
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

Price trends for Condo Rentals in Winter Garden

Less expensive
More expensive
Next month
October
December
$156
Month
Price
January
$156
February
$166
March
$165
April
$150
May
$151
June
$155
July
$162
August
$167
September
$137
October
$134
November
$142
December
$188
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed Condo Rentals in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Winter Garden

Winter Garden Condo Rentals information

Number of reviews
1
Accommodation
5870 Condo Rentals
Lowest Price
$237
Highest Price
$308

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.

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