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Check prices for these dates

Next weekend
Jul 3 - Jul 5
In two weeks
Jul 10 - Jul 12
In one month
Jul 24 - Jul 26
In two months
Aug 21 - Aug 23

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, (141 reviews)
"Our first experience with a B&B - but won't be our last! Very cute and unique house and the host makes a great breakfast! Everything provided that you might need - including some drinks and snacks! Nice to be able to visit and get suggestions from someone who knows the area."
United States
Laura
The price is ₩239,850
₩272,230 total
includes taxes & fees
Jun 28 - Jun 29
Kapp and Kappy B&B
Outdoor pool

Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
5.8 out of 10, (8 reviews)
"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 ₩83,302
₩199,603 total
includes taxes & fees
Jun 26 - Jun 27
Hotel Styled Bedrooms in a Villa
Exterior

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
4.6 out of 10, (4 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 ₩82,825
₩178,657 total
includes taxes & fees
Jul 3 - Jul 4
Styled Bedrooms in a Resort
Outdoor pool

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 ₩83,302
₩199,603 total
includes taxes & fees
Jun 26 - Jun 27
The Gathering Place
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
The price is ₩245,232
₩1,118,250 total
includes taxes & fees
Jul 8 - Jul 9
The Tiny Cottage in The Springs
Exterior

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is ₩901,056
₩1,473,395 total
includes taxes & fees
Jun 29 - Jun 30
Oakland Manor House
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Loved this property"
Kellie 6-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Windermere

Windermere B&B information

Number of reviews
181
Accommodation
7 B&B
Lowest Price
₩178,657
Highest Price
₩1,473,395

Frequently asked questions

Searching for B&Bs in Windermere?
If you're looking for something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. If you're interested in playing some golf on your trip, Isleworth Golf and Country Club is a good spot to tee off.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to interact with the owner, and top-rated breakfasts, B&Bs offer a truly one-of-a-kind environment.
What are the best B&Bs in Windermere?
Here are some B&Bs in the area: Kapp and Kappy B&B: 3 rooms. 15.9 mi (25.5 km) from the downtown core. Enjoy the free full breakfast and unique décor. Hotel Styled Bedrooms in a Villa: 4 rooms. Situated 14.7 mi (23.6 km) from the heart of Windermere. The Gathering Place: 14.6 mi (23.6 km) from the heart of downtown. Styled Bedrooms in a Resort: 6 rooms. Located 18.4 mi (29.7 km) from the core of Windermere.
What's the best time of year to stay at a B&B in Windermere?
When you're dreaming of a getaway to Windermere, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Windermere are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What is there to do in Windermere?
Spend some time exploring Lake Butler and Tibet Butler Preserve if you're hoping to see some of the area's natural features. You might check out Isleworth Golf and Country Club if you have time to see more of the area.
How can I get to and around Windermere?
You can plan your excursions in and around Windermere ahead of time with these transportation options. Fly into Orlando Intl. Airport (MCO), which is located 14.5 mi (23.3 km) away from the city center. Otherwise, look for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 15.2 mi (24.4 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.