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Winter Garden Vacation Rentals

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Our top choices for Winter Garden vacation rentals

Upstay: Condo Near Disney w Pool, Sauna

Upstay: Condo Near Disney w Pool, Sauna
3.5 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
$216 nightly
The price is $243
Jun 24 - Jun 25
Total with taxes and fees
Upstay: Condo Near Disney w Pool, Sauna

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, (19 reviews)
$253 nightly
The price is $281
Jun 23 - Jun 24
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL

StylishAptWtrGrdnOppLake&Prk&Yrd

StylishAptWtrGrdnOppLake&Prk&Yrd
Winter Garden
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay! "
United States
Lindsey W.
$187 nightly
The price is $200
Jun 22 - Jun 23
Total with taxes and fees
StylishAptWtrGrdnOppLake&Prk&Yrd

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, (7 reviews)
"Place was clean and excellent location and club amenities "
United States
Anonymous traveler
$293 nightly
The price is $326
Jun 23 - Jun 24
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

Relaxing retreat w/ pool & BBQ grill

Relaxing retreat w/ pool & BBQ grill
Winter Garden
2.0 out of 10, (1 review)
"If you like camping in a tent with campfires to cook and cold water to shower, then THIS is the place for you! Hot water was in short supply, Air Conditioning broke down, the oven did not work (this was the number one reason we chose this place), we saw cockroaches in the kitchen, no handle on the entry door, no hand towels, one washcloth, neighbors are 5 feet away and LOVE to blast their radios early in the morning and late at night, sheets are scratchy, and the refrigerator leaked and...
United States
Peter
$214 nightly
The price is $222
Jun 24 - Jun 25
Total with taxes and fees
Relaxing retreat w/ pool & BBQ grill

FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.2 out of 10, Wonderful, (9 reviews)
"Host was very responsive and easy to work with and wanted to make sure we had a great stay. The location is perfect & easy to walk downtown and get to the bike trails. The property is a little smaller or feels smaller than the photos but it was clean and had great amenities."
United States
Cheri S.
$208 nightly
The price is $223
Jul 2 - Jul 3
Total with taxes and fees
FunTropicalTinyHomeGolfCartLake

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$486 nightly
The price is $544
Jun 30 - Jul 1
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

The Oak View Place..

The Oak View Place..
Oakland
9.2 out of 10, Wonderful, (10 reviews)
"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."
United States
Libba F.
$259 nightly
The price is $288
Jun 22 - Jun 23
Total with taxes and fees
The Oak View Place..

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
"One of best VRBO’s we have stayed. Very well set up and very warm and comfortable. Felt like home. And the location is perfect. We will be back. "
United States
John T.
$491 nightly
The price is $542
Jun 30 - Jul 1
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!

Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney
2.0 star property
Winter Garden
$237 nightly
The price is $266
Jun 22 - Jun 23
Total with taxes and fees
Upstay 3BR Condo w Pool Patio Near Disney

Modern 3BR Resort Condo With Pool Near Disney

Modern 3BR Resort Condo With Pool Near Disney
4.0 star property
Winter Garden
$227 nightly
The price is $255
Jun 25 - Jun 26
Total with taxes and fees
Modern 3BR Resort Condo With Pool Near Disney

Family Fun Condo Pool and Sauna near Disney

Family Fun Condo Pool and Sauna near Disney
Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"Clean, nicely appointed apartment close to Disney. Great pet friendly location. Will stay again. Highly recommend! "
United States
John and Dawn R.
$220 nightly
The price is $247
Jun 24 - Jun 25
Total with taxes and fees
Family Fun Condo Pool and Sauna near Disney

Upstay Family-Friendly Condo w Pool Near Disney

Upstay Family-Friendly Condo w Pool Near Disney
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"Perfect stay, clean and comfortable. Just minutes from theme parks. The owner was very helpful and quick to respond! Would stay again! "
United States
Dennis K.
$249 nightly
The price is $280
Jun 25 - Jun 26
Total with taxes and fees
Upstay Family-Friendly Condo w Pool Near Disney

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
Winter Garden
10.0 out of 10, Exceptional, (33 reviews)
"Great location and a comfortable stay. "
United States
Tim S.
$600 nightly
The price is $648
Jul 12 - Jul 13
Total with taxes and fees
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

Studio Near Disney World

Studio Near Disney World
Kissimmee
$185 nightly
The price is $200
Jul 13 - Jul 14
Total with taxes and fees
Studio Near Disney World

Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
10.0 out of 10, Exceptional, (1 review)
"We had a spectacular time at the Oakland Manor House. It's a gorgeous, historic home filled with both handsome antiques and comfortable sofas and beds. The kitchen is fully stocked and a joy to use to make meals if you're so inclined. The bathrooms were very clean and well appointed with bath products and hair dryers for use. They even had coffee beans and a grinder for use. Very nice gestures. It was spotless and located in a lovely, safe neighborhood. We had a celebration of our wedding with...
United States
Kristen R.
$1,082 nightly
The price is $1,160
Jun 22 - Jun 23
Total with taxes and fees
Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$249 nightly
The price is $279
Jun 22 - Jun 23
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
$243 nightly
The price is $266
Jul 13 - Jul 14
Total with taxes and fees
1-Bedroom Villa Near Disney w/ Pool & Lazy River

Upstay - 3BR Condo w Pool and Sauna

Upstay - 3BR Condo w Pool and Sauna
3.5 star property
Winter Garden
$224 nightly
The price is $252
Jun 22 - Jun 23
Total with taxes and fees
Upstay - 3BR Condo w Pool and Sauna

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

Upstay - Condo Near Disney w Pool-spa-sauna-games
2.0 star property
Winter Garden
$227 nightly
The price is $255
Jul 15 - Jul 16
Total with taxes and fees
Upstay - Condo Near Disney w Pool-spa-sauna-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

Price trends for vacation rentals in Winter Garden

Less expensive
More expensive
Next month
April
February
$217
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?

The Berkley, Orlando: This vacation home rental near Winter Garden offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Garden?

With 5 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 Butler and Lake Louisa State Park 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.