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

Winter Garden Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winter Garden vacation rentals

Interior

1. Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
4.0 star property
Winter Garden
$243 nightly
The price is $273
Oct 16 - Oct 17
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

2. 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, (24 reviews)
"The property was perfect for our week with family"
United States
Steve S.
$308 nightly
The price is $342
Nov 1 - Nov 2
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
Pool

3. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Lindsey W.
$189 nightly
The price is $202
Oct 19 - Oct 20
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd
Interior

4. 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.
$209 nightly
The price is $224
Oct 16 - Oct 17
Total with taxes and fees
FunTropicalTinyHomeGolfCartLake
A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

5. 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
$374 nightly
The price is $415
Oct 20 - Oct 21
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

6. Cozy 1-bedroom with AC in awesome Winter Garden

Cozy 1-bedroom with AC in awesome Winter Garden
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and had a great experience. Gina communicated with us right away, so we knew how to check in or had any questions answered. The property is very cute and looks new and was spotless. The location of the property is great as well. Downtown Winter Garden is adorable with great restaurants and is an easy drive down Plant St. It also was very convenient to where we were visiting in Ocoee and Orlando.We had everything we needed, highly recommend this property, and would stay there...
United States
Anonymous traveler
$317 nightly
The price is $352
Oct 20 - Oct 21
Total with taxes and fees
Cozy 1-bedroom with AC in awesome Winter Garden
Room

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

Modern 3BR Condo Near Disney- Pool and Hot Tub
2.0 star property
Winter Garden
$222 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
Modern 3BR Condo Near Disney- Pool and Hot Tub
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$444 nightly
The price is $499
Oct 18 - Oct 19
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
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.

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
$245 nightly
The price is $274
Oct 20 - Oct 21
Total with taxes and fees
Family-Friendly 2BR Condo w Resort Pool & Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

10. Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
$220 nightly
The price is $248
Nov 2 - Nov 3
Total with taxes and fees
Condo With Sauna, Games, Poolnear Disney
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

11. 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.
$452 nightly
The price is $502
Oct 18 - Oct 19
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

12. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$239 nightly
The price is $268
Oct 18 - Oct 19
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

13. 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.
$252 nightly
The price is $282
Oct 18 - Oct 19
Total with taxes and fees
Upstay - Condo w Pool and More - Near Disney
Communal Outdoor Pool and Hot Tub

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

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
$275 nightly
The price is $309
Oct 16 - Oct 17
Total with taxes and fees
Upstay: Stylish 3BR Condo w Patio—near Disney
Resort Amenities

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

Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Winter Garden
$244 nightly
The price is $273
Oct 18 - Oct 19
Total with taxes and fees
Upstay 3BR Suite w Pool, Sauna & Games—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.

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

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$243 nightly
The price is $272
Oct 18 - Oct 19
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym
Room

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

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
$233 nightly
The price is $233
Nov 2 - Nov 3
Total with taxes and fees
Upstay - Condo Near Disney w Pool Hot tub Sauna
Resort Amenities

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

Spacious Resort Suite w/ Pool & Sauna near Disney
Winter Garden
$225 nightly
The price is $252
Nov 2 - Nov 3
Total with taxes and fees
Spacious Resort Suite w/ Pool & Sauna near Disney
A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

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

Upstay Modern Condo w Pool—10 minutes to Disney
Winter Garden
$236 nightly
The price is $264
Oct 18 - Oct 19
Total with taxes and fees
Upstay Modern Condo w Pool—10 minutes to Disney
A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

20. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
$201 nightly
The price is $226
Oct 19 - Oct 20
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"I has all the plates, silverware and glassware you need. Big fridge and plenty of space. Pools, restaurant's and property is beautiful."
Mark 1-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Price trends for vacation rentals in Winter Garden

Less expensive
More expensive
Next month
April
February
$235
Month
Price
January
$287
February
$293
March
$221
April
$202
May
$202
June
$220
July
$217
August
$213
September
$219
October
$223
November
$235
December
$284
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 vacation rentals in Winter Garden. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Winter Garden

Everything you need to know about Winter Garden vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Garden vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Garden vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Garden vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Garden. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Garden in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $92 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Garden rentals

At Expedia, we put the best Winter Garden vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Garden rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Garden vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Garden. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.