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Winter Garden Vacation Rentals

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Vacation Rentals in Winter Garden

Water-view Villa: Patio, Pool Access 4Mi to Disney

Water-view Villa: Patio, Pool Access 4Mi to Disney

Winter Garden, FL

Set in Winter Garden, this family-friendly villa is within 9 mi (15 km) of Lake Davenport, Disney's Blizzard Beach Water Park, and Fun Spot America. Disney's ...

4.3/5Excellent! (21 reviews)
Friendly, helpful management

"Had excellent help getting sister who arrived before me into property and came in to replace torn shower curtain. Very helpful!"…"

Reviewed on Apr. 14, 2021

Water-view Villa: Patio, Pool Access 4Mi to Disney
Entire home 4 miles from Disney

Entire home 4 miles from Disney

Winter Garden, FL

Set in Winter Garden, this family-friendly vacation home is within 9 mi (15 km) of Lake Davenport, Disney's Blizzard Beach Water Park, and Disney's Animal Kingdom® ...

5/5Exceptional! (1 review)
A Gateway to Disney

"A very good property located near Disney World. Both host and caretaker, are very helpful. Enjoyed my vacations a lot. A good place to stay for Disney vacations."…"

Reviewed on Oct. 14, 2019

Entire home 4 miles from Disney
Cute House by the Lake Near Disney World

Cute House by the Lake Near Disney World

Winter Garden, FL
The price is CA $99 per night from Apr 19 to Apr 20

Located in West Kissimmee, this vacation home is within 6 mi (10 km) of Lake Davenport, Disney's Blizzard Beach Water Park, and Disney's Winter Summerland Miniature ...

5/5Exceptional! (22 reviews)
Quiet neighborhood with great location

"I took my mother on a birthday trip along with our (2) pets. We booked a 5 night stay and had a wonderful time. The place is located in a very quiet neighborhood. The location is very close to the parks and other fun locations. There is a pleasant view of a pond. We saw lots of wildlife during our ..."…"

Reviewed on Apr. 12, 2021

Cute House by the Lake Near Disney World
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Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!

Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $110 per night from Apr 26 to Apr 27

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

5/5Exceptional! (2 reviews)
Great stay in Orlando

"My husband and I came to stay at the property for something work related. The space is tastefully decorated with open layout and ample space. It was also centrally located and close to many good restaurants and stores. Thank you for a great stay!"…"

Reviewed on Mar. 24, 2021

Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!
Chill out in a Relaxing 3 Bed/2 Bath Home, With Lake Views, Near to Disney

Chill out in a Relaxing 3 Bed/2 Bath Home, With Lake Views, Near to Disney

Winter Garden, FL

Located on the waterfront, this family-friendly vacation home is within 6 mi (10 km) of Lake Davenport, Disney's Blizzard Beach Water Park, and Disney's Winter ...

4.7/5Exceptional! (29 reviews)
Had a wonderful stay

"We stayed here for overnight sleeping. We didn't cook except to make tea each morning. We didn't use any of the facilities in the area because of Covid concerns. My family was visiting my mother who lives close by so this was excellent for us to visit them all day and return here to sleep at night. ..."…"

Reviewed on Jan. 6, 2021

Chill out in a Relaxing 3 Bed/2 Bath Home, With Lake Views, Near to Disney
New! Winter Garden House w/ Lanai + Pool Access!

New! Winter Garden House w/ Lanai + Pool Access!

Winter Garden, FL

Located in West Kissimmee, this vacation home is within 9 mi (15 km) of Lake Davenport, Disney's Blizzard Beach Water Park, and Disney's Animal Kingdom® Theme ...

New! Winter Garden House w/ Lanai + Pool Access!
Full Service Resort & Water Park Near Disney, 3 Bedroom 3 Bath

Full Service Resort & Water Park Near Disney, 3 Bedroom 3 Bath

Winter Garden, FL

Situated in Winter Garden, this vacation home is within 9 mi (15 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Disney's Boardwalk. Lake Davenport ...

3/5 (1 review)
Nice property but .....

"Layout of the condo was perfect for our family. The living area, kitchen, laundry and rooms/beds/bathrooms were great. However many frustrations onsite. Given wrong room type (we reserved 3 bedroom/3 bath, given 2 bedroom/2 bath) by front desk and had to repack everything (didnt realize it was not ..."…"

Reviewed on Apr. 2, 2021

Full Service Resort & Water Park Near Disney, 3 Bedroom 3 Bath
Full Service Resort & Water Park Near Disney, 2 Bedroom 2 Bath

Full Service Resort & Water Park Near Disney, 2 Bedroom 2 Bath

Winter Garden, FL

Situated in Winter Garden, this aparthotel is within 9 mi (15 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Disney's Boardwalk. Lake Davenport ...

Full Service Resort & Water Park Near Disney, 2 Bedroom 2 Bath
The Oak View Place.

The Oak View Place.

Winter Garden, FL
The price is CA $124 per night from Apr 18 to Apr 19

Located in Oakland, this historic apartment building is 1.1 mi (1.7 km) from Oakland Nature Preserve and within 3 mi (5 km) of Winter Garden Art Association ...

5/5Exceptional! (4 reviews)
Holiday Stay

"Nice room and location. Very Clean.easy access. Vrbo listed as 2 bedrooms. Should be 2 beds. Enjoyed our stay Would have liked to have a microwave but still a great place."…"

Reviewed on Dec. 30, 2020

The Oak View Place.
Near Disney - Stunning 3BR - Family Resort With Pool and Hot Tub!

Near Disney - Stunning 3BR - Family Resort With Pool and Hot Tub!

Winter Garden, FL
The price is CA $124 per night from Apr 20 to Apr 21

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Near Disney - Stunning 3BR - Family Resort With Pool and Hot Tub!
Family Resort - Spacious 3BR Near Disney - Pool and Hot Tub!

Family Resort - Spacious 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $104 per night from Apr 19 to Apr 20

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Family Resort - Spacious 3BR Near Disney - Pool and Hot Tub!
Family Resort - Spacious 3BR Condo - Pool and Hot Tub!

Family Resort - Spacious 3BR Condo - Pool and Hot Tub!

Winter Garden, FL
The price is CA $124 per night from Apr 20 to Apr 21

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

4/5Very Good! (1 review)
Nice and affordable

"I would definitely stay again!! Communication was excellent with the owner, my dogs were welcome and the accommodations were very nice!!"…"

Reviewed on Mar. 25, 2021

Family Resort - Spacious 3BR Condo - Pool and Hot Tub!
Family Resort - Modern 3BR Near Disney - Pool and Hot Tub!

Family Resort - Modern 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $104 per night from Apr 19 to Apr 20

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Family Resort - Modern 3BR Near Disney - Pool and Hot Tub!
Family Resort - Stunning 3BR Near Disney - Pool and Hot Tub!

Family Resort - Stunning 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $124 per night from Apr 20 to Apr 21

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

5/5Exceptional! (1 review)
Spacious and comfortable

"We had a family of 4 adults and a pet black lab. We stayed on the fourth floor. Nice 3 bedroom 2 bath . One bath connected to the master. Comfortable balcony with access from the bedrooms and living room. We had plenty of linens and paper products for our 3 night stay. We were within 30 mins to all ..."…"

Reviewed on Apr. 5, 2021

Family Resort - Stunning 3BR Near Disney - Pool and Hot Tub!
Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!

Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $124 per night from Apr 26 to Apr 27

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Family Resort - Luxury 3BR Near Disney - Pool and Hot Tub!
Family Resort - Relaxing 3BR Near Disney - Pool and Hot Tub!

Family Resort - Relaxing 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $124 per night from Apr 20 to Apr 21

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Family Resort - Relaxing 3BR Near Disney - Pool and Hot Tub!
Luxury 3BR Near Disney - Family Resort - Pool and Hot Tub!

Luxury 3BR Near Disney - Family Resort - Pool and Hot Tub!

Winter Garden, FL
The price is CA $104 per night from Apr 19 to Apr 20

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Luxury 3BR Near Disney - Family Resort - Pool and Hot Tub!
Upscale 3BR Near Disney - Family Resort With Pool and Hot Tub!

Upscale 3BR Near Disney - Family Resort With Pool and Hot Tub!

Winter Garden, FL
The price is CA $111 per night from Apr 19 to Apr 20

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

Upscale 3BR Near Disney - Family Resort With Pool and Hot Tub!
Family Resort - Upscale 3BR Near Disney - Pool and Hot Tub!

Family Resort - Upscale 3BR Near Disney - Pool and Hot Tub!

Winter Garden, FL
The price is CA $104 per night from Apr 19 to Apr 20

Located in West Kissimmee, this romantic resort is within 6 mi (10 km) of Island H2O Live!, Lake Davenport, and Highland Reserve Golf Club. Disney's Blizzard ...

5/5Exceptional! (1 review)
Very nice condo and close to Disney.

"Very good and timely communication with owner. Condo was very nice and clean property was just as advertised. Pool closes at 5 so was not able to enjoy it after going to Disney for the day. Would highly recommend this property."…"

Reviewed on Mar. 21, 2021

Family Resort - Upscale 3BR Near Disney - Pool and Hot Tub!
Water Park + Pool On-site Shuttle to Disney World

Water Park + Pool On-site Shuttle to Disney World

Winter Garden, FL
The price is CA $351 per night from Apr 18 to Apr 19

Situated in Winter Garden, this condo building is within 9 mi (15 km) of Island H2O Live!, Disney's Blizzard Beach Water Park, and Lake Davenport. Highland Reserve ...

4.8/5Exceptional! (8 reviews)
I was over charged upon departure and still trying to go refund I’m due. Will dispute entire charge

"You get what you pay for"…"

Reviewed on Jul. 13, 2020

Water Park + Pool On-site Shuttle to Disney World
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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.

Other types of properties in Winter Garden you may be interested in

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
The price is CA $243 per night from Apr 19 to Apr 20
The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

4 out of 5
8505 W Irlo Bronson Memorial Hwy, Winter Garden, FL
The price is CA $179 per night from Apr 19 to Apr 20
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Garden. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Winter Garden?
Yes, we offer vacation rentals in Winter Garden close to Central Florida Railroad Museum, 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?
Entire Home 4 Miles From Disney: This highly rated vacation home rental in Winter Garden offers an outdoor pool, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with an arcade game room and a hot tub. Some other homes for rent in Winter Garden include Winter / Summer Vacation Home and Cute House by the Lake Near Disney World.
How many vacation rentals are there in Winter Garden?
With 54 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?
Cultural attractions include Winter Garden Art Association and Central Florida Railroad Museum, whereas Lake Louisa State Park and Lake Butler are a couple of picturesque spots to enjoy the outdoors. Walt Disney World® and Magic Kingdom® Park 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.