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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Winter Garden

Porch
Kapp and Kappy B&B

Kapp and Kappy B&B

3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (125)
"Friendly host. Felt like home. "
Canada
Gordon
The price is SAR 551
SAR 626 total
includes taxes & fees
18 Dec - 19 Dec
Kapp and Kappy B&B
Outdoor pool, sun loungers
Heron Cay Lakeview Bed & Breakfast Inn

Heron Cay Lakeview Bed & Breakfast Inn

3.5 star property
Mount Dora
9.4 out of 10, Exceptional, (156)
"Very clean and welcoming environment. The host was extremely welcoming and accommodating with a delicious breakfast! Within walking distance to downtown too. I would return if vacationing in the area."
United States
Ed
The price is SAR 769
SAR 854 total
includes taxes & fees
11 Dec - 12 Dec
Heron Cay Lakeview Bed & Breakfast Inn
Front of property
Adora Inn

Adora Inn

3.5 star property
Mount Dora
9.8 out of 10, Exceptional, (86)
"Friendly staff who made this short anniversary getaway a lovely time. Within walking distance to the shops and restaurants."
United States
Denise
The price is SAR 799
SAR 976 total
includes taxes & fees
16 Dec - 17 Dec
Adora Inn
Design Room | Living area | 40-inch Smart TV with digital channels, TV
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)
"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 SAR 600
SAR 2,549 total
includes taxes & fees
5 Jan - 6 January 2026
The Tiny Cottage in The Springs
Front of property
Mount Dora Historic Inn

Mount Dora Historic Inn

2.5 star property
Mount Dora
9.6 out of 10, Exceptional, (236)
"Beautiful and charming, room was very clean, great location with parking, owner is very friendly and accommodating."
United States
Bradford
The price is SAR 980
SAR 1,087 total
includes taxes & fees
7 Jan - 8 January 2026
Mount Dora Historic Inn
Outdoor pool
Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa

3.0 star property
Kissimmee
6.0 out of 10, (6)
"I didn’t know it was a house being shared by like 6 other tenants and parking was a pain"
United States
Veronica
The price is SAR 166
SAR 443 total
includes taxes & fees
2 Jan - 3 January 2026
Hotel Styled Bedrooms in a Villa
Shared kitchen
The Gathering Place

The Gathering Place

2.0 star property
Kissimmee
2.0 out of 10, (1)
"Not to clean or to friendly "
United States
Tier
The price is SAR 198
SAR 224 total
includes taxes & fees
7 Jan - 8 January 2026
The Gathering Place
Outdoor pool
Styled Bedrooms in a Resort

Styled Bedrooms in a Resort

2.0 star property
Solterra Resort
3.0 out of 10, (2)
"Uncleanliness "
United States
Gina
The price is SAR 146
SAR 373 total
includes taxes & fees
1 Jan - 2 January 2026
Styled Bedrooms in a 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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"The room was very clean and the staff were very courteous."
Steven 3-night trip
Posted 13 hours ago
Rosen Inn Lake Buena Vista

Frequently asked questions

Searching for B&Bs in Winter Garden?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to get some local recommendations, a B&B can be a good choice for many different types of travelers. 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 a B&B for your stay?
With attentive service, opportunities to meet guests from other places, and hearty breakfasts, B&Bs provide a truly one-of-a-kind setting.
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.Mount Dora Historic Inn: 4 rooms. 16.6 mi (26.7 km) from the downtown core. Enjoy the free full breakfast and unique décor. Heron Cay Lakeview Bed & Breakfast Inn: 8 rooms. Located 16.9 mi (27.1 km) from the core of Winter Garden. Enjoy the in-room pools and private yard.
What's the best time of year to book my B&B in Winter Garden?
When you're planning your getaway to Winter Garden, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Garden are August, July, September, and June, with each month seeing an average of 9 inches of rainfall.
What is there to do in Winter Garden?
Travelers who want to experience Winter Garden should check out 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 might 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?
Mapping out your trip in and around Winter Garden is easy with these transportation options. Fly into Orlando Intl. Airport (MCO), which is located 19.3 mi (31 km) from the city center. Otherwise, you can search for flights to Kissimmee, FL (ISM-Kissimmee Gateway), which is 20.8 mi (33.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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