Winter Garden Vacation Rentals

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Our top choices for Winter Garden vacation rentals

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.
The price is ¥22,463
¥58,095 total
includes taxes & fees
Mar 30 - Mar 31
Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ¥29,337
¥81,540 total
includes taxes & fees
Apr 2 - Apr 3
Fire Pit & Yard: Updated Winter Garden Home!

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
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfortable place. The location is great and Gina did a good jon communicating all the details. "
United States
Scott S.
The price is ¥17,313
¥52,982 total
includes taxes & fees
Mar 30 - Mar 31
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, (21 reviews)
"Communication was good, was clean and kitchen was well stocked. "
United States
Anonymous traveler
The price is ¥16,672
¥32,062 total
includes taxes & fees
Apr 6 - Apr 7
StylishAptWtrGrdnOppLake&Prk&Yrd

FunTropicalTinyHomeGolfCartLake

FunTropicalTinyHomeGolfCartLake
Winter Garden
9.0 out of 10, Wonderful, (8 reviews)
"For those with furry friends who want to see Orlando and Central Florida there aren't a lot of affordable options so this is a wonderful go to. It's like 'glamping' in a Winter Gardens neighborhood across from a wonderful park on a lake for walking your 4 legged family members. Owner is a great communicator ready to answer any questions to help make your stay great. "
United States
Brian R.
The price is ¥19,237
¥34,947 total
includes taxes & fees
Apr 12 - Apr 13
FunTropicalTinyHomeGolfCartLake

Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
The price is ¥21,349
¥52,232 total
includes taxes & fees
Apr 22 - Apr 23
Upstay Condo w Pool Sauna Sleeps 8

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
The price is ¥16,191
¥45,056 total
includes taxes & fees
Mar 30 - Mar 31
Upstay - Pet-Friendly Condo - Sauna, 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.
The price is ¥28,856
¥45,488 total
includes taxes & fees
Mar 30 - Mar 31
The Oak View Place..

Spacious 3BR Family Getaway w Pool near Disney

Spacious 3BR Family Getaway w Pool near Disney
Winter Garden
7.6 out of 10, Good, (5 reviews)
"The parking garage was very difficult to navigate. The spaces were extremely tight, and the exits were awkwardly designed. The condo itself was fine overall. However, the shower in the secondary bathroom (not connected to the master) had very poor water pressure. The pool area was nice, but unfortunately the hot tub jets were not working during our stay. On a positive note, the location was excellent and made getting to and from Disney very convenient."
United States
Liz
The price is ¥12,985
¥45,057 total
includes taxes & fees
Apr 27 - Apr 28
Spacious 3BR Family Getaway w Pool near Disney

Emerald Grove - Close to Disney

Emerald Grove - Close to Disney
Winter Garden
10.0 out of 10, Exceptional, (1 review)
"Everything was great"
United States
Marie E.
The price is ¥52,101
¥81,438 total
includes taxes & fees
Apr 16 - Apr 17
Emerald Grove - Close to Disney

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.
The price is ¥72,140
¥166,062 total
includes taxes & fees
Mar 30 - Mar 31
Central Florida's Historic Gem & wedding venue- The Oakland Manor House

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

Near Disney - Family Condo w Pool, Games, and More
Winter Garden
The price is ¥17,955
¥50,697 total
includes taxes & fees
Apr 26 - Apr 27
Near Disney - Family Condo w Pool, Games, and More

Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
Winter Garden
The price is ¥15,229
¥47,604 total
includes taxes & fees
Apr 13 - Apr 14
Upstay Condo Near Disney w Pool & Sauna

Winter Garden Family-friendly Condo w Resort Pool

Winter Garden Family-friendly Condo w Resort Pool
Winter Garden
The price is ¥12,504
¥44,991 total
includes taxes & fees
Mar 30 - Mar 31
Winter Garden Family-friendly Condo w Resort Pool

Modern 3BR Condo w Private Patio 7min to Disney

Modern 3BR Condo w Private Patio 7min to Disney
Winter Garden
The price is ¥13,947
¥46,148 total
includes taxes & fees
Apr 21 - Apr 22
Modern 3BR Condo w Private Patio 7min to Disney

Upstay Amazing Disney Condo w Patio Sleeps 6

Upstay Amazing Disney Condo w Patio Sleeps 6
2.0 star property
Winter Garden
The price is ¥23,720
¥51,114 total
includes taxes & fees
Apr 12 - Apr 13
Upstay Amazing Disney Condo w Patio Sleeps 6

Upstay: Resort Condo with Pool & Sauna—Near Disney

Upstay: Resort Condo with Pool & Sauna—Near Disney
Winter Garden
The price is ¥14,268
¥46,513 total
includes taxes & fees
Apr 21 - Apr 22
Upstay: Resort Condo with Pool & Sauna—Near Disney

Upstay: Stylish Resort Getaway w/ Pool near Disney

Upstay: Stylish Resort Getaway w/ Pool near Disney
Winter Garden
The price is ¥17,955
¥50,697 total
includes taxes & fees
Apr 26 - Apr 27
Upstay: Stylish Resort Getaway w/ Pool near Disney

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

1-Bedroom Villa Near Disney w/ Pool & Lazy River
Kissimmee
The price is ¥26,953
¥40,563 total
includes taxes & fees
Apr 27 - Apr 28
1-Bedroom Villa Near Disney w/ Pool & Lazy River

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.
The price is ¥14,428
¥43,055 total
includes taxes & fees
Mar 30 - Mar 31
Family Fun Condo Pool and 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

Find out more about Winter Garden

Search for holiday rentals in Winter Garden on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Garden using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winter Garden!

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 3 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.