Winter Garden Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Winter Garden holiday rentals

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
The price is HK$809
HK$2,101 total
includes taxes & fees
11 Feb - 12 Feb
Upstay Amazing Disney Condo w Patio Sleeps 6
Outdoor spa tub

Hawthorn Extended Stay by Wyndham Orlando

Hawthorn Extended Stay by Wyndham Orlando
3.0 star property
Orlando
7.8 out of 10, Good, (1,003 reviews)
"The room was nice and clean. Plenty of parking on-site. The hotel itself is a short drive away from restaurants and a gas station."
United States
Jason
Hawthorn Extended Stay by Wyndham Orlando
Exterior

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,014 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is HK$484
HK$727 total
includes taxes & fees
11 Feb - 12 Feb
voco Kissimmee Orlando by IHG
Restaurant

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

Fairfield Inn & Suites Orlando Int'l Drive/Convention Center
2.5 star property
International Drive District
8.6 out of 10, Excellent, (1,005 reviews)
"Excelent location, clean room and the staff is great"
United States
Maite
The price is HK$813
HK$914 total
includes taxes & fees
22 Feb - 23 Feb
Fairfield Inn & Suites Orlando Int'l Drive/Convention Center
Outdoor pool, pool umbrellas, pool loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,822 reviews)
"Great place. To stay "
United States
THOMAS
Barefoot Suites
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,796 reviews)
"Cottage was very clean and easy check in close to all dining and shopping "
United States
Fernando
The price is HK$1,711
HK$3,506 total
includes taxes & fees
10 Feb - 11 Feb
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (36 reviews)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages
Property amenity

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (528 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is HK$977
HK$1,234 total
includes taxes & fees
10 Feb - 11 Feb
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

Siena at Bella Collina

Siena at Bella Collina
3.5 star property
Montverde
9.8 out of 10, Exceptional, (71 reviews)
"Property exceptional!! Room for everyone in our family to have privacy. View so relaxing and beautiful sunrise over the lake. "
United States
Sandra
The price is HK$3,578
HK$3,971 total
includes taxes & fees
16 Feb - 17 Feb
Siena at Bella Collina
Exterior

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,062 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
The price is HK$1,259
HK$2,973 total
includes taxes & fees
23 Feb - 24 Feb
Regal Oaks Resort Vacation Townhomes by IDILIQ
Full-sized fridge, microwave, oven, stovetop

Leisure Lounge

Leisure Lounge
3.5 star property
Solterra Resort
8.4 out of 10, Very good, (17 reviews)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is HK$336
HK$902 total
includes taxes & fees
12 Mar - 13 Mar
Leisure Lounge
Waterslide

Champions Gate Resort Home w BBQ Pool

Champions Gate Resort Home w BBQ Pool
2.0 star property
Champions Gate
9.4 out of 10, Exceptional, (9 reviews)
"Very relaxing and my property assistant was great over the phone "
United States
Robert
Champions Gate Resort Home w BBQ Pool
Restaurant

Crofton Springs House 4 Bedroom

Crofton Springs House 4 Bedroom
3.5 star property
Providence
10.0 out of 10, Exceptional, (1 review)
The price is HK$2,245
HK$5,440 total
includes taxes & fees
13 Feb - 14 Feb
Crofton Springs House 4 Bedroom
2 outdoor pools, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers

The Village Resort Suite and Spa

The Village Resort Suite and Spa
2.5 star property
Orlando
The price is HK$410
HK$3,245 total
includes taxes & fees
10 Feb - 11 Feb
The Village Resort Suite and Spa
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers

Marriott's Sabal Palms

Marriott's Sabal Palms
4.0 star property
Orlando
9.6 out of 10, Exceptional, (212 reviews)
"Room was great, staff friendly and grounds are clean. "
United States
DENNIS
The price is HK$2,055
HK$2,312 total
includes taxes & fees
4 Mar - 5 Mar
Marriott's Sabal Palms
Interior entrance

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.8 out of 10, Excellent, (3 reviews)
"Amazing "
United States
Nilda
The price is HK$469
HK$1,050 total
includes taxes & fees
12 Feb - 13 Feb
Jade Manor
Living area

304 Lakeshore - Unit 1 and 2

304 Lakeshore - Unit 1 and 2
2.0 star property
Historic Downtown Kissimmee
The price is HK$586
HK$1,759 total
includes taxes & fees
9 Mar - 10 Mar
304 Lakeshore - Unit 1 and 2
Private kitchen

Davenport Vacation Homes by Shine FM

Davenport Vacation Homes by Shine FM
4.0 star property
Tuscan Hills
8.4 out of 10, Very good, (26 reviews)
"it was a great property to stay in!"
United States
Nancy
The price is HK$852
HK$1,881 total
includes taxes & fees
10 Feb - 11 Feb
Davenport Vacation Homes by Shine FM
Private kitchen

Century Millenia

Century Millenia
3.0 star property
Florida Center
9.0 out of 10, Wonderful, (109 reviews)
"Beautiful place to stay and loved that it had washer and dryer on site. Super helpful for a longer stay. Definitely recommend staying here! "
United States
Collin
Century Millenia
Exterior

WorldQuest Orlando Resort

WorldQuest Orlando Resort
4.0 star property
Orlando
8.4 out of 10, Very good, (4,045 reviews)
"No complaints, wonderful resort. "
United States
Nigel
WorldQuest Orlando Resort
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

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Rooms are comfortable and well equipped. Breakfast was sufficient and the coffee 24/7 was a plus. "
Sigifredo A 15-night trip
Posted 4 hours ago
Homewood Suites by Hilton Orlando at Flamingo Crossings

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:

  • View our selection of featured holiday rentals in Winter Garden
  • Use the map to find apartments and other holiday homes in the Winter Garden neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Garden while they last

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

Frequently asked questions

Can I find a holiday rental in Winter Garden?

Yes, there are holiday rentals in Winter Garden close to Surfari Water Park, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Winter Garden has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Garden offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Garden?

With 4 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Winter Garden?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Garden. Holiday rentals feature amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.