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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winter Garden vacation rentals

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$455 nightly
The price is $511
Oct 2 - Oct 3
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

2. Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
8.0 out of 10, Very good, (1 review)
"The condo was perfect for our blended family. We enjoyed the space, including the balcony overseeing the pool. My kids enjoyed the game room. Host was friendly/responsive. Was able to work through an unexpected challenge and find reasonable solution. The condo has definitely been well used and could use some updating. I can send a list to host if requested. Overall we had a great stay, conveniently located to stores/restaurants. Had most of the basic supplies needed."
United States
Andrea Nicole
$228 nightly
The price is $257
Sep 29 - Sep 30
Total with taxes and fees
Upstay Condo w Pool Sauna Sleeps 8
A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

3. Upstay Modern Condo w Pool10 Minutes to Disney

Upstay Modern Condo w Pool10 Minutes to Disney
3.5 star property
Winter Garden
$210 nightly
The price is $237
Oct 1 - Oct 2
Total with taxes and fees
Upstay Modern Condo w Pool10 Minutes to Disney

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

Upstay - Condo Near Disney w Pool Hot tub Sauna
2.0 star property
Winter Garden
$230 nightly
The price is $230
Sep 29 - Sep 30
Total with taxes and fees
Upstay - Condo Near Disney w Pool Hot tub Sauna
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

5. Near Disney - Family Condo w Pool, Games, and More

Near Disney - Family Condo w Pool, Games, and More
3.0 star property
Winter Garden
6.0 out of 10, (1 review)
"You get what you pay for for sure! This was a place to stay that was clean inside, just very outdated and the hall smell was SO HORRIBLE. They have fragrance machines throughout the halls to where you can literally taste the fragrance. It was going into our room and we all felt nauseous because of how strong it was. I also would like to recommend the place gets carts so guests can easily transfer their belongings from the parking garage to their room because it was a FAR walk with all of our...
United States
Aubree
$218 nightly
The price is $245
Sep 29 - Sep 30
Total with taxes and fees
Near Disney - Family Condo w Pool, Games, and More

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

Upstay - Condo w Hot Tub and Pool - Near Disney
2.0 star property
Winter Garden
$232 nightly
The price is $232
Sep 29 - Sep 30
Total with taxes and fees
Upstay - Condo w Hot Tub and Pool - Near Disney
A swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

7. Upstay Large Family Condo w Pool, Sauna

Upstay Large Family Condo w Pool, Sauna
3.5 star property
Winter Garden
$211 nightly
The price is $237
Oct 1 - Oct 2
Total with taxes and fees
Upstay Large Family Condo w Pool, Sauna

8. 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
Oct 1 - Oct 2
Total with taxes and fees
Modern 3BR Condo Near Disney- Pool and Hot Tub

9. Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
3.0 star property
Winter Garden
$218 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
Upstay Condo Near Disney w Pool & Sauna

10. Upstay Tropical Style Family Condo w Pool

Upstay Tropical Style Family Condo w Pool
2.0 star property
Winter Garden
$217 nightly
The price is $245
Sep 29 - Sep 30
Total with taxes and fees
Upstay Tropical Style Family Condo w Pool
A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

11. Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
$212 nightly
The price is $238
Oct 4 - Oct 5
Total with taxes and fees
Modern 3BR Resort Condo With 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.

12. Upstay - Condo Near Disney w Pool-spa-sauna-games

Upstay - Condo Near Disney w Pool-spa-sauna-games
2.0 star property
Winter Garden
$207 nightly
The price is $233
Sep 29 - Sep 30
Total with taxes and fees
Upstay - Condo Near Disney w Pool-spa-sauna-games

13. Upstay Stylish 3BR Condo w Patio Near Disney

Upstay Stylish 3BR Condo w Patio Near Disney
2.0 star property
Winter Garden
$232 nightly
The price is $261
Sep 30 - Oct 1
Total with taxes and fees
Upstay Stylish 3BR Condo w Patio Near Disney

14. Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney
2.0 star property
Winter Garden
$247 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
Upstay 3BR Condo w Pool Patio Near Disney

15. Upstay - Modern Family Apartment w Pool Hot Tub

Upstay - Modern Family Apartment w Pool Hot Tub
2.0 star property
Winter Garden
$228 nightly
The price is $228
Sep 30 - Oct 1
Total with taxes and fees
Upstay - Modern Family Apartment w Pool Hot Tub
A laundry area with a washing machine, dryer, and a wall-mounted decorative piece.

16. Upstay Large Family Condo w Pool Sauna

Upstay Large Family Condo w Pool Sauna
2.0 star property
Winter Garden
$230 nightly
The price is $259
Oct 1 - Oct 2
Total with taxes and fees
Upstay Large Family Condo w Pool Sauna
A dining area with a table set for four, a sofa in the background, and a kitchen area with a dishwasher.

17. Upstay: Condo Near Disney w Games, Pool

Upstay: Condo Near Disney w Games, Pool
3.5 star property
Winter Garden
$215 nightly
The price is $242
Oct 4 - Oct 5
Total with taxes and fees
Upstay: Condo Near Disney w Games, Pool

18. Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
4.0 star property
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"The unit was very clean and organized when we arrived. All the amenities and appliances that come with the unit worked amazing. The only exception was the WiFi. It was a bit slow, however this could be easily fixed and should not discourage from booking this property. Being at the pool was the highlight of staying at this property. It was clean and came with fun pool sized amenities like pool basketball and connect 4. Being in the lobby was also fun with the ping pong table and pool table. The...
United States
Nancy
$215 nightly
The price is $242
Sep 29 - Sep 30
Total with taxes and fees
Upstay: Condo Near Disney w Pool, Sauna

19. Upstay - Condo w Pool - Near Disney!

Upstay - Condo w Pool - Near Disney!
3.5 star property
Winter Garden
$215 nightly
The price is $241
Oct 1 - Oct 2
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.

20. Upstay Disney Pet Friendly Condo w Pool Spa Games

Upstay Disney Pet Friendly Condo w Pool Spa Games
4.0 star property
Winter Garden
$201 nightly
The price is $226
Oct 1 - Oct 2
Total with taxes and fees
Upstay Disney Pet Friendly Condo w Pool Spa Games
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Rooms were spacious and clean!! Love the lazy River! The breakfast was delicious! Would stay again!"
Kimberly 2-night trip
Posted 3 hours ago
Kompose Boutique Resort at Theme Parks

Price trends for vacation rentals in Winter Garden

Less expensive
More expensive
Next month
April
February
$223
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 $95 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.