A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

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)
"The room was really nice and the breakfast was great."
United States
Mark
The price is ฿5,394
฿6,123 total
includes taxes & fees
11 Nov - 12 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, (180 reviews)
"Great location, beautiful decor"
United States
Shawn
The price is ฿6,852
฿7,606 total
includes taxes & fees
21 Oct - 22 Oct
Heron Cay Lakeview Bed & Breakfast Inn
A modern living room with a white sofa, a dining table with chairs, a fireplace, and a staircase leading to an upper level.

3. 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 ฿5,344
฿24,368 total
includes taxes & fees
23 Oct - 24 Oct
The Tiny Cottage in The Springs
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 ฿8,987
฿9,976 total
includes taxes & fees
22 Oct - 23 Oct
Mount Dora Historic Inn
A spacious living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

5. Tempo Room Lodgings

Tempo Room Lodgings
3.0 star property
Kissimmee
The price is ฿1,775
฿4,302 total
includes taxes & fees
31 Oct - 1 Nov
Tempo Room Lodgings
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 ฿1,805
฿4,325 total
includes taxes & fees
21 Oct - 22 Oct
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 ฿1,785
฿3,871 total
includes taxes & fees
23 Oct - 24 Oct
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 ฿1,360
฿3,831 total
includes taxes & fees
21 Oct - 22 Oct
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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Top Winter Garden Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"★★★★★ Great family stay, but the dryers need some Disney magic! We were really pleased with Home2 Suites at Flamingo Crossings! Our king suite gave us privacy while the kids slept in the living room, and the kitchen setup with a sink and dining table was incredibly convenient. The rooms and property were clean and well maintained, and the staff was friendly and courteous. The girls loved the breakfast buffet options, and we all enjoyed the pool and slide. Nearby stores and restaurants made everything easy. Parking could get tight when returning late from the parks, but that’s understandable at a busy hotel. My main suggestion is to repair the laundry equipment. Several dryers tumbled without heat, and a couple of washers had spin-cycle issues. At $3 a cycle, our clothes were getting plenty of rides but very little drying! What should have been a quick chore turned into three hours of dryer roulette. We found a laundromat about 1.5 miles away that I’d use next time. Still a five-star stay overall, and we’d happily return!"
Ryan 6-night trip
Posted 5 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden B&B information

Number of reviews
615
Accommodation
13 B&B
Lowest Price
฿3,831
Highest Price
฿24,368

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.