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Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

Our top choices for Windermere bed & breakfast

Porch

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (129 reviews)
"Loved the front porch. Yummy breakfast. Very hospitable "
United States
Linda
$169 nightly
The price is $192
Feb 16 - Feb 17
Total with taxes and fees
Kapp and Kappy B&B
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 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
$678 nightly
The price is $699
Feb 21 - Feb 22
Total with taxes and fees
The Tiny Cottage in The Springs
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 reviews)
"I didn’t know it was a house being shared by like 6 other tenants and parking was a pain"
United States
Veronica
$108 nightly
The price is $123
Feb 14 - Feb 15
Total with taxes and fees
Hotel Styled Bedrooms in a Villa
Smart TV

3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends

3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends
Clermont
$269 nightly
The price is $295
Feb 19 - Feb 20
Total with taxes and fees
3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends
Outdoor pool

The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
2.0 out of 10, (1 review)
"Not to clean or to friendly "
United States
Tier
$112 nightly
The price is $128
Mar 10 - Mar 11
Total with taxes and fees
The Gathering Place
Exterior

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
3.0 out of 10, (2 reviews)
"Uncleanliness "
United States
Gina
$100 nightly
The price is $111
Feb 10 - Feb 11
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 Windermere Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"The rooms were pretty cool. The staff was nice and the game room. The kids loved the game room lol"
Justin 1-night trip
Posted 1 day ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Find out more about Windermere

Windermere B&B information

Number of reviews
138
Accommodation
27 B&B
Lowest Price
$111
Highest Price
$699

Frequently asked questions

What is the nightly rate for a B&B in Windermere?
Prices for B&Bs in Windermere often vary, but you can find a great deal from $111 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windermere 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.
When is the best time to book a Bed and Breakfast in Windermere?
The most popular time to book a B&B in Windermere is from July to September, when the area comes alive with outdoor enthusiasts seeking the stunning landscapes and recreational activities that this beautiful region offers. During these peak months, visitors can enjoy warm temperatures averaging in the mid-70s to low 80s Fahrenheit, making it ideal for hiking, boating, and exploring the charming local attractions.

July stands out as the busiest month, with an array of festivals and events drawing crowds from near and far. Adventurers can take advantage of the long, sunny days to experience everything from tranquil boat rides on the lake to invigorating hikes along scenic trails that overlook breathtaking vistas.

For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, superb for enjoying the tranquility of the area while still taking in the beautiful fall foliage. Crisp autumn air presents an excellent opportunity for leisurely walks and cozy evenings by the fireplace.
What is the difference between a Windermere Bed and Breakfast and a hotel?
Every Windermere 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 Windermere B&Bs.

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