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Winter Garden Vacation Rentals

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Our top choices for Winter Garden vacation rentals

1. Upstay: Stylish 3BR Condo w Pationear Disney

Upstay: Stylish 3BR Condo w Pationear Disney
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"The room was great, spacious, clean, just what we needed. All the amenities were as promised. We loved the stay."
United States
Ismael
$208 nightly
The price is $234
Dec 1 - Dec 2
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney

2. 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, (9 reviews)
"The house is absolutely beautiful! We stayed for two nights and had a wonderful experience. Communication with the host was excellent throughout our stay. We really enjoyed our time there and would definitely recommend this place!"
United States
isaac
$369 nightly
The price is $412
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

3. FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.4 out of 10, Exceptional, (11 reviews)
"We had a great time! The host was spectacular. Our accommodations were very clean and comfortable! "
United States
Emily R.
$178 nightly
The price is $191
Dec 1 - Dec 2
Total with taxes and fees
FunTropicalTinyHomeGolfCartLake

4. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay! "
United States
Lindsey W.
$178 nightly
The price is $191
Dec 6 - Dec 7
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd

5. 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.
$288 nightly
The price is $323
Nov 10 - Nov 11
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

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
$310 nightly
The price is $345
Nov 16 - Nov 17
Total with taxes and fees
Cozy 1-bedroom with AC in awesome Winter Garden

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
$226 nightly
The price is $226
Nov 29 - Nov 30
Total with taxes and fees
Modern 3BR Condo Near Disney- Pool and Hot Tub

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
Nov 8 - Nov 9
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

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

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
$245 nightly
The price is $276
Dec 1 - Dec 2
Total with taxes and fees
Upstay: Stylish 3BR Condo w Patio—near Disney

10. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
$232 nightly
The price is $261
Nov 18 - Nov 19
Total with taxes and fees
Modern 3BR Resort Condo With Pool Near Disney

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.
$429 nightly
The price is $479
Nov 8 - Nov 9
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

12. 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)
"Super 2 bed 2 bath property walking distance to Winter Garden downtown area."
United States
Ron C.
House with large deck, walking distance to Historic Downtown Winter Garden

13. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$246 nightly
The price is $277
Dec 1 - Dec 2
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool

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

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$231 nightly
The price is $261
Nov 30 - Dec 1
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
$215 nightly
The price is $242
Nov 11 - Nov 12
Total with taxes and fees
Family-Friendly 2BR Condo w Resort Pool & Sauna

16. Studio Near Disney World Resort with Pools + more

Studio Near Disney World Resort with Pools + more
Kissimmee
$202 nightly
The price is $220
Nov 16 - Nov 17
Total with taxes and fees
Studio Near Disney World Resort with Pools + more

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 30 - Dec 1
Total with taxes and fees
Upstay - Condo Near Disney w Pool Hot tub Sauna

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

Upstay 3BR Suite w Pool, Sauna & Games—Near Disney
Winter Garden
$235 nightly
The price is $266
Nov 30 - Dec 1
Total with taxes and fees
Upstay 3BR Suite w Pool, Sauna & Games—Near Disney

19. Upstay: 3BR Family Condo w Pool & Sauna

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
$246 nightly
The price is $277
Dec 1 - Dec 2
Total with taxes and fees
Upstay: 3BR Family Condo w Pool & Sauna

20. Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
$224 nightly
The price is $252
Nov 30 - Dec 1
Total with taxes and fees
Condo With Sauna, Games, Poolnear 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

Price trends for vacation rentals in Winter Garden

Less expensive
More expensive
This month
Next month
April
February
$235
$284
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 $93 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.