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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winter Garden bed & breakfast

A covered porch with wooden chairs and a ceiling fan.

1. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (147 reviews)
"An amazing experience. Freindly hosts. If we go to Orlando again we will rwbook"
United States
THOMAS
The price is S$234
includes taxes & fees
9 Nov - 10 Nov
Kapp and Kappy B&B
A large, multi-story house with a porch and a driveway.

2. Heron Cay Lakeview Bed & Breakfast Inn

Heron Cay Lakeview Bed & Breakfast Inn
3.5 star property
Mount Dora
9.4 out of 10, Exceptional, (182 reviews)
"Great location, beautiful decor"
United States
Shawn
The price is S$292
includes taxes & fees
10 Nov - 11 Nov
Heron Cay Lakeview Bed & Breakfast Inn
A rectangular swimming pool with a hot tub, surrounded by a brick patio and palm trees.

3. Tempo Room Lodgings

Tempo Room Lodgings
3.0 star property
Kissimmee
The price is S$151
includes taxes & fees
8 Dec - 9 Dec
Tempo Room Lodgings
A two-story house with a front porch, a red door, and an American flag.

4. Mount Dora Historic Inn

Mount Dora Historic Inn
2.5 star property
Mount Dora
9.6 out of 10, Exceptional, (252 reviews)
"Clean room and great location!"
United States
Jeanie
The price is S$417
includes taxes & fees
12 Nov - 13 Nov
Mount Dora Historic Inn
A modern living room with a white sofa, a dining table with chairs, a fireplace, and a staircase leading to an upper level.

5. The Tiny Cottage in The Springs

The Tiny Cottage in The Springs
4.0 star property
Altamonte Springs
9.8 out of 10, Exceptional, (26 reviews)
"I really like this place, this is the second time I have booked here. I do consider it whenever I travel to the area."
United States
Anastasia
The price is S$921
includes taxes & fees
9 Dec - 10 Dec
The Tiny Cottage in The Springs
A pool area with a clear view of the surrounding buildings, a blue inflatable shark, and several lounge chairs.

6. Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
5.8 out of 10, (8 reviews)
"Parking was almost a mile away. Didn’t even get to stay there and wasted over $200 on the stay. Communication was bad. I tried to get a refund because of the parking situation, they never got back to me. "
United States
Chantal
The price is S$163
includes taxes & fees
10 Nov - 11 Nov
Hotel Styled Bedrooms in a Villa
A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

7. Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
5.6 out of 10, (5 reviews)
"I was very comfortable with the people that were staying there. Very nice place. Would recommend anyone to stay."
United States
Jason
The price is S$148
includes taxes & fees
10 Nov - 11 Nov
Styled Bedrooms in a Resort
A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

8. The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
5.0 out of 10, (2 reviews)
"clean room and bathroom"
United States
Matthew
The price is S$145
includes taxes & fees
8 Dec - 9 Dec
The Gathering Place
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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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
A brick building with a clock tower and a sign that reads "Winter Garden."

Frequently Asked Questions

Searching for B&Bs in Winter Garden?

Whether you're travelling with your family and want a friendly place to stay, or you're travelling solo and hoping to make some connections, B&Bs can be a great choice for many travellers. If you want to lose yourself exploring fascinating exhibits, you might consider stopping by Central Florida Railroad Museum and Winter Garden Heritage Museum while you're in town.

Are you thinking about apartments over traditional hotel rooms?

With attentive service, opportunities to socialise with other guests and of course a full breakfast, B&Bs offer a unique environment.

What are the top B&Bs in Winter Garden?

Here are some well-liked B&Bs in the area: Oakland Manor House: 5 rooms. 2.5 mi (4.1 km) from the heart of Winter Garden. Heron Cay Lakeview Bed & Breakfast Inn: 8 rooms. 16.9 mi (27.1 km) from the city centre. Enjoy the in-room pools and private garden. Mount Dora Historic Inn: 4 rooms. Situated 16.6 mi (26.7 km) from the heart of Winter Garden. Enjoy the free full breakfast and unique decor. Adora Inn: 5 rooms. 16.7 mi (26.8 km) from the city centre. Enjoy the free full breakfast and massage services.

When should I book my B&B in Winter Garden?

When you're planning your escape to Winter Garden, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Garden are August, July, September and June, with each month seeing an average of 217 mm of rainfall.

What is there to do in Winter Garden?

Travellers who want to experience Winter Garden should visit its fun-filled attractions and major shopping area. If you're looking for some activities to entertain you on your trip, consider visiting Orange County National Golf Club and Disney's Magnolia Golf Course. You should put Lake Louisa State Park and Disney's Palm Golf Course on your list if you want to see more of the area.

How can I get to and around Winter Garden?

You can plan your excursions in and around Winter Garden ahead of time with these transportation options. Fly into Orlando International Airport (MCO), which is located 19.3 mi (31 km) from the city centre. Otherwise, look for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 20.8 mi (33.5 km) away. If you'd like to explore around the area, consider renting a car to explore more sights.