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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$205 nightly
The price is $231
Oct 29 - Oct 30
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney
A living room with a sofa, two armchairs, a coffee table, and artwork on the wall.

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.
$310 nightly
The price is $344
Nov 10 - Nov 11
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

3. 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
$314 nightly
The price is $349
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom with AC in awesome Winter Garden
Living area

4. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Lindsey W.
$192 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd
A living room with a beige sofa, yellow armchair, and a white coffee table. There are large windows with blinds, a ceiling fan, and a flat-screen TV on the wall.

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
$371 nightly
The price is $412
Oct 25 - Oct 26
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Communal Outdoor Pool and Hot Tub

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

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
$234 nightly
The price is $263
Oct 25 - Oct 26
Total with taxes and fees
Upstay: Stylish 3BR Condo w Patio—near Disney
Interior

7. 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.
$211 nightly
The price is $227
Oct 26 - Oct 27
Total with taxes and fees
FunTropicalTinyHomeGolfCartLake
Room

8. Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
2.0 star property
Winter Garden
$240 nightly
The price is $269
Oct 25 - Oct 26
Total with taxes and fees
Upstay Stylish 3BR Condo w Patio Near Disney
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

9. 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 25 - Oct 26
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A poolside area with lounge chairs and a sofa, a pool, and a building with vertical wooden slats.

10. Luxury Retreat, Close to Disney

Luxury Retreat, Close to Disney
Winter Garden
$397 nightly
The price is $397
Oct 29 - Oct 30
Total with taxes and fees
Luxury Retreat, Close to Disney
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

11. Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
$228 nightly
The price is $257
Nov 18 - Nov 19
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.

12. 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.
$449 nightly
The price is $499
Oct 25 - Oct 26
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.

13. 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, (29 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.
$371 nightly
The price is $412
Nov 8 - Nov 9
Total with taxes and fees
House with large deck, walking distance to Historic Downtown Winter Garden
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

14. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$251 nightly
The price is $281
Oct 26 - Oct 27
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool
Resort Amenities

15. Upstay - Condo w Pool - Near Disney!

Upstay - Condo w Pool - Near Disney!
Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"It was a very nice condo. "
United States
Mellodie L.
$239 nightly
The price is $268
Oct 25 - Oct 26
Total with taxes and fees
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.

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
$251 nightly
The price is $281
Oct 29 - Oct 30
Total with taxes and fees
Family-Friendly 2BR Condo w Resort Pool & Sauna
Stunning Aerial View Of The Property Surrounded By Nature

17. Family Fun Condo Pool and Sauna near Disney

Family Fun Condo Pool and Sauna near Disney
Winter Garden
9.6 out of 10, Exceptional, (5 reviews)
"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "
United States
John and Dawn R.
$235 nightly
The price is $263
Oct 25 - Oct 26
Total with taxes and fees
Family Fun Condo Pool and Sauna near Disney
Room

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

Upstay - Condo w Hot Tub and Pool - Near Disney
2.0 star property
Winter Garden
$249 nightly
The price is $249
Oct 25 - Oct 26
Total with taxes and fees
Upstay - Condo w Hot Tub and Pool - 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.

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

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$245 nightly
The price is $274
Nov 18 - Nov 19
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym
Resort Amenities

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

Spacious Resort Suite w/ Pool & Sauna near Disney
Winter Garden
$223 nightly
The price is $249
Oct 26 - Oct 27
Total with taxes and fees
Spacious Resort Suite w/ Pool & Sauna 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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"We enjoyed every moment. Coming back next year."
Carolina 5-night trip
Posted 5 hours ago
Universal's Cabana Bay Beach Resort

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 $88 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.