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

Winter Garden Vacation Rentals

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Our top choices for Winter Garden vacation rentals

1. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay! "
United States
Lindsey W.
$174 nightly
The price is $187
Nov 18 - Nov 19
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd

2. 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.
$175 nightly
The price is $188
Nov 12 - Nov 13
Total with taxes and fees
FunTropicalTinyHomeGolfCartLake

3. 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.
$291 nightly
The price is $326
Nov 11 - Nov 12
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

4. 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
$359 nightly
The price is $402
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

5. 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 11 - Nov 12
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

6. 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
$201 nightly
The price is $226
Nov 30 - Dec 1
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney

7. 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
$316 nightly
The price is $353
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom with AC in awesome Winter Garden

8. Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
2.0 star property
Winter Garden
$235 nightly
The price is $264
Nov 11 - Nov 12
Total with taxes and fees
Upstay Stylish 3BR Condo w Patio Near Disney

9. 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.
$417 nightly
The price is $467
Nov 11 - Nov 12
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

10. 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, (30 reviews)
"This was our second time staying here. Just as great as the first time!"
United States
Thomas C.
House with large deck, walking distance to Historic Downtown Winter Garden

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

Upstay: Stylish 3BR Condo w Patio—near Disney
Winter Garden
$226 nightly
The price is $255
Nov 12 - Nov 13
Total with taxes and fees
Upstay: Stylish 3BR Condo w Patio—near Disney

12. 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

13. Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$226 nightly
The price is $255
Nov 12 - Nov 13
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
$206 nightly
The price is $232
Nov 11 - Nov 12
Total with taxes and fees
Family-Friendly 2BR Condo w Resort Pool & Sauna

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

Upstay: 3BR Family Condo w Pool & Sauna
Winter Garden
$226 nightly
The price is $255
Nov 11 - Nov 12
Total with taxes and fees
Upstay: 3BR Family Condo w Pool & Sauna

16. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
$231 nightly
The price is $260
Nov 15 - Nov 16
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna

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.
$214 nightly
The price is $242
Nov 11 - Nov 12
Total with taxes and fees
Family Fun Condo Pool and Sauna near Disney

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

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
$229 nightly
The price is $229
Nov 18 - Nov 19
Total with taxes and fees
Upstay - Condo Near Disney w Pool Hot tub Sauna

19. Upstay - Pet-Friendly Condo - Sauna, Pool

Upstay - Pet-Friendly Condo - Sauna, Pool
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"Very clean and spacious great location. Would definitely come back "
United States
KELLEE
$227 nightly
The price is $256
Nov 17 - Nov 18
Total with taxes and fees
Upstay - Pet-Friendly Condo - Sauna, Pool

20. Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
Winter Garden
$222 nightly
The price is $251
Nov 30 - Dec 1
Total with taxes and fees
Upstay Modern 2BR Condo 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

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 $91 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.