Winter Garden Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Winter Garden vacation rentals

Interior

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, (5 reviews)
"Beautiful apartment, close to downtown. The host, Gina, was super helpful. The gym in the complex is very nice. We would definitely stay again. "
United States
Sarah R.
$319 nightly
The price is $354
Apr 14 - Apr 15
Total with taxes and fees
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
Microwave, oven, stovetop, dishwasher

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, (13 reviews)
"Very clean and comfortable place. The location is great and Gina did a good jon communicating all the details. "
United States
Scott S.
$305 nightly
The price is $339
Apr 20 - Apr 21
Total with taxes and fees
Modern LuXuRy Unit in beautiful Down Town Winter Garden with WIFI, Cable & POOL
House (2 Bedrooms) | Interior

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 $509
Apr 16 - Apr 17
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Lobby

Winter Garden Charm, Near Disney

Winter Garden Charm, Near Disney
Winter Garden
8.8 out of 10, Excellent, (3 reviews)
"Our host Sebastian was very responsive to our questions, and the apartment is just like it is shown in the pictures. Very modern, clean, and the beds were comfortable. And, the property is just a over a mile and a half from downtown Winter Garden.The only issue I would note is that the unit is located at the very front of the complex, right along the road. So, you can definitely hear the cars when they go by. "
United States
John E.
$358 nightly
The price is $358
Apr 13 - Apr 14
Total with taxes and fees
Winter Garden Charm, Near Disney
Apartment

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
2.0 star property
Winter Garden
$225 nightly
The price is $256
Apr 14 - Apr 15
Total with taxes and fees
Upstay Modern 2BR Condo Near Disney
Property grounds

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 $254
Apr 13 - Apr 14
Total with taxes and fees
Upstay - Pet-Friendly Condo - Sauna, Pool
Outdoor pool

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.
$254 nightly
The price is $283
Apr 13 - Apr 14
Total with taxes and fees
The Oak View Place..
TV

Upstay - Large Condo Near Disney w Pool and Gym

Upstay - Large Condo Near Disney w Pool and Gym
Winter Garden
$252 nightly
The price is $283
Apr 26 - Apr 27
Total with taxes and fees
Upstay - Large Condo Near Disney w Pool and Gym
Lobby

Emerald Grove - Close to Disney

Emerald Grove - Close to Disney
Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great"
United States
Marie E.
$505 nightly
The price is $505
Apr 16 - Apr 17
Total with taxes and fees
Emerald Grove - Close to Disney
Exterior

Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
$241 nightly
The price is $270
Apr 13 - Apr 14
Total with taxes and fees
Upstay Condo Near Disney w Pool & Sauna
Interior

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

Near Disney - Family Condo w Pool, Games, and More
Winter Garden
$243 nightly
The price is $272
Apr 13 - Apr 14
Total with taxes and fees
Near Disney - Family Condo w Pool, Games, and More
TV

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

Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
$264 nightly
The price is $283
Apr 20 - Apr 21
Total with taxes and fees
Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Exterior

Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
$255 nightly
The price is $285
Apr 13 - Apr 14
Total with taxes and fees
Winter Garden Family-friendly Condo w Resort Pool
Pool

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
$248 nightly
The price is $271
May 10 - May 11
Total with taxes and fees
1-Bedroom Villa Near Disney w/ Pool & Lazy River
Apartment | 2 bedrooms, Internet

Upstay Amazing Disney Condo w Patio Sleeps 6

Upstay Amazing Disney Condo w Patio Sleeps 6
2.0 star property
Winter Garden
$228 nightly
The price is $256
Apr 13 - Apr 14
Total with taxes and fees
Upstay Amazing Disney Condo w Patio Sleeps 6
Pool

Studio Near Disney World

Studio Near Disney World
Kissimmee
$202 nightly
The price is $219
Apr 28 - Apr 29
Total with taxes and fees
Studio Near Disney World
Interior

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.
$1,090 nightly
The price is $1,168
Apr 19 - Apr 20
Total with taxes and fees
Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Exterior

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"we had a wonderful stay at Palisades resort on 4th floor (top floor) . Condo was very spacious/clean and close to Disney amd rte 192. 2 very large bedrooms (with own bathrooms ) kitchen/living room/dining area in between, great for privacy. huge screened in patio, with views of nightly disney fireworks exterior of bldg could have been kept up better. trash/garbage visible as you pull into parking garage, and very messy/scattered around. other than that, property was great and would stay there...
United States
Kristi F.
$221 nightly
The price is $248
May 5 - May 6
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna
Exterior

Family-Friendly Condo with Pool & Sauna

Family-Friendly Condo with Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"This 2 bedroom apartment was perfect for us. Clean and well kept. Very spacious rooms with comfortable beds. I would recommend this place. "
United States
Samuel L.
$221 nightly
The price is $248
May 5 - May 6
Total with taxes and fees
Family-Friendly Condo with Pool & Sauna
TV

Upstay Condo with Outdoor Pool & Sauna

Upstay Condo with Outdoor Pool & Sauna
Winter Garden
10.0 out of 10, Exceptional, (2 reviews)
"The check in process was easy and quick. We had self check in and 2 balconies the view was amazing! We loved everything about this property"
United States
Trennecia B.
$224 nightly
The price is $251
Apr 13 - Apr 14
Total with taxes and fees
Upstay Condo with Outdoor Pool & Sauna
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

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

10/10 Excellent
"From easy checking in and out to the close parking, nice staff, the wonderful room, the pools, the cleanliness and all the amenities we had the absolute best time staying here and highly recommend this property for your vacation or just because. 10 out of 10 for sure and we can’t wait to come back. "
Alexander 6-night trip
Posted 2 hours ago
Hilton Vacation Club Aqua Sol Orlando West

Price trends for vacation rentals in Winter Garden

Less expensive
More expensive
This month
Next month
June
February
$214
$214
Month
Price
January
$225
February
$266
March
$234
April
$214
May
$214
June
$205
July
$216
August
$219
September
$212
October
$208
November
$219
December
$242
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?

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 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.