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Our top choices for Winter Garden bed & breakfast

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
$152 nightly
The price is $173
Dec 22 - Dec 23
Total with taxes and fees
Kapp and Kappy B&B

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
$678 nightly
The price is $699
Dec 22 - Dec 23
Total with taxes and fees
The Tiny Cottage in The Springs

Adora Inn

Adora Inn
3.5 star property
Mount Dora
9.8 out of 10, Exceptional, (88)
"Loved our 2-nite stay at Adora. John and Arthur were exceptional hosts and a great source of local recommendations. Room Treetop was spacious bright and super clean. Big soaking tub was a special treat. And the best part was starting each morning w John’s phenomenal gourmet breakfasts! "
United States
patricia
$205 nightly
The price is $228
Jan 20 - Jan 21, 2026
Total with taxes and fees
Adora Inn

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
$205 nightly
The price is $228
Jan 6 - Jan 7, 2026
Total with taxes and fees
Heron Cay Lakeview Bed & Breakfast Inn

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
$261 nightly
The price is $290
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mount Dora Historic Inn

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
$109 nightly
The price is $124
Jan 2 - Jan 3, 2026
Total with taxes and fees
Hotel Styled Bedrooms in a Villa

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
$53 nightly
The price is $61
Jan 20 - Jan 21, 2026
Total with taxes and fees
The Gathering Place

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
$89 nightly
The price is $100
Jan 1 - Jan 2, 2026
Total with taxes and fees
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

Find out more about Winter Garden

Winter Garden B&B information

Number of reviews
612
Accommodation
32 B&B
Lowest Price
$61
Highest Price
$699

Frequently asked questions

What is the nightly rate for a B&B in Winter Garden?
Prices for B&Bs in Winter Garden often vary, but you can find a great deal from $61 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winter Garden B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
Are there any family-friendly Bed and Breakfasts in Winter Garden?
The Edgewater Hotel is a fantastic choice for families visiting Winter Garden. This charming property features a lovely garden where kids can play and explore, providing a serene backdrop for family bonding. Its proximity to nearby theme parks ensures that your family can easily dive into adventure during your stay. Additionally, the hotel offers a convenient snack bar, superb for quick bites after a day of fun.

Another excellent family-friendly option is Oakland Manor House. This delightful B&B is designed with families in mind, boasting a dedicated games area for children, which is sure to keep the little ones entertained. The well-equipped kitchen allows families to prepare their own meals, making it easier to accommodate various dietary preferences. Surrounded by a beautiful garden and also located near theme parks, Oakland Manor House offers a superb blend of relaxation and adventure for families visiting the area.
Do any Winter Garden Bed & Breakfasts allow dogs?
Oakland Manor House is a fantastic choice for dog lovers visiting Winter Garden, FL. This charming property not only permits pets but also features a dedicated dog exercise area, ensuring your furry friend can enjoy their stay just as much as you do. The comfortable accommodations are complemented by a partial lake view, allowing you to unwind on your furnished balcony or patio while soaking in the serene surroundings.
Are there any romantic Bed & Breakfasts in Winter Garden for couples?
For a romantic getaway in Winter Garden, Oakland Manor House offers a charming and inviting space that couples will adore. This delightful bed and breakfast features beautifully appointed rooms with a terrace and furnished balconies, superb for enjoying a morning coffee or an evening glass of wine while taking in the partial lake views.
Which area is best to stay in a Winter Garden B&B?
For travelers looking for an ideal B&B experience in Winter Garden, Bay Lake stands out as the most popular choice among our guests. This area provides a serene atmosphere with close proximity to the natural beauty of the lakes, great for family outings or peaceful retreats.

Families will appreciate the nearby Historic Downtown Winter Garden, which features the vibrant Plant Street Market, a hub of local shops and restaurants. This lively market is great for enjoying fresh produce and artisanal goods, while the Garden Theatre offers an array of entertainment options. The West Orange Trail is another highlight, ideal for biking or walking, ensuring that active families have plenty to explore together.

Couples seeking a romantic getaway will find the charm of Bay Lake appealing. The tranquil lakeside setting provides opportunities for scenic picnics and sunset views. The local dining scene, with its variety of restaurants, offers intimate settings for a delightful evening out.
When is the best time to book a B&B in Winter Garden?
The best time to book a B&B in Winter Garden is during the peak season, which spans from January to March. This period is particularly appealing for travelers eager to bask in the pleasant Florida sunshine while enjoying the vibrant local culture. With temperatures typically ranging from the low 50s to mid-70s Fahrenheit, visitors can comfortably explore the charming downtown area, filled with boutique shops and delightful eateries.

January to March also brings a plethora of outdoor activities, from leisurely strolls along the West Orange Trail to engaging in the seasonal farmers' markets. The community atmosphere is vibrant during these months, making it an ideal time for sightseeing and mingling with locals and fellow travelers alike.

For those seeking a more budget-friendly experience, consider visiting in October. This month offers a quieter ambiance, allowing for a more relaxed exploration of the area's picturesque parks and gardens. The fall season brings a lovely array of colors and a chance to enjoy the outdoors without the crowds, making it a great time for leisurely bike rides or family picnics.
What is the difference between a Winter Garden Bed and Breakfast and a hotel?
Every Winter Garden B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winter Garden B&Bs.

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