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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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

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a refrigerator.

1. 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
Oct 22 - Oct 23
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.

2. 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 22 - Oct 23
Total with taxes and fees
Cozy 1-bedroom with AC in awesome Winter Garden
Interior

3. 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 25 - Oct 26
Total with taxes and fees
Upstay: Stylish 3BR Condo w Pationear Disney
A spacious lobby with a high ceiling, exposed brick walls, and modern lighting fixtures.

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, (8 reviews)
"Place was clean and excellent location and club amenities "
United States
Anonymous traveler
$371 nightly
The price is $412
Oct 22 - Oct 23
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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
Oct 25 - Oct 26
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Interior

6. 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
Pool

7. StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (24 reviews)
"Great place to stay! "
United States
Lindsey W.
$199 nightly
The price is $213
Nov 2 - Nov 3
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd
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!
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.

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, (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.
$288 nightly
The price is $320
Oct 28 - Oct 29
Total with taxes and fees
House with large deck, walking distance to Historic Downtown Winter Garden
A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

11. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
$216 nightly
The price is $243
Oct 25 - Oct 26
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna
Discover the winding lazy river, perfect for a refreshing float on a sunny day.

12. Studio Near Disney World Resort with Pools + more

Studio Near Disney World Resort with Pools + more
Kissimmee
$201 nightly
The price is $218
Oct 26 - Oct 27
Total with taxes and fees
Studio Near Disney World Resort with Pools + more
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.

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

Family-Friendly 2BR Condo w Resort Pool & Sauna
Winter Garden
Family-Friendly 2BR Condo w Resort Pool & Sauna
Discover the winding lazy river, perfect for a refreshing float on a sunny day.

14. 1-Bedroom Villa Near Disney w/ Pool & Lazy River

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
$227 nightly
The price is $248
Oct 26 - Oct 27
Total with taxes and fees
1-Bedroom Villa Near Disney w/ Pool & Lazy River
A wooden deck with a hot tub, a wooden dock extending into a body of water, and a view of the water and sky.

15. WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (34 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
$692 nightly
The price is $750
Oct 31 - Nov 1
Total with taxes and fees
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Aerial View Of The Resort-Style Complex Featuring A Large Pool And Serene Surroundings

16. 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
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 22 - Oct 23
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
$261 nightly
The price is $261
Oct 25 - Oct 26
Total with taxes and fees
Upstay - Condo w Hot Tub and Pool - Near Disney
Discover the winding lazy river, perfect for a refreshing float on a sunny day.

19. Studio Near Disney World

Studio Near Disney World
Kissimmee
$186 nightly
The price is $201
Oct 26 - Oct 27
Total with taxes and fees
Studio Near Disney World
Stunning Aerial View Of The Property Surrounded By Nature

20. Family-friendly Condo w/ Pool & Sauna—near Disney

Family-friendly Condo w/ Pool & Sauna—near Disney
Winter Garden
$235 nightly
The price is $263
Oct 22 - Oct 23
Total with taxes and fees
Family-friendly Condo 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
"100 % recommended 👍 👍"
Karen a. 1-night trip
Posted 3 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 $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.