A lakeside community with houses and boats.

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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Windermere bed & breakfast

Pool

1. 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 ₩75,006
₩179,721 total
includes taxes & fees
Aug 21 - Aug 22
Hotel Styled Bedrooms in a Villa
Porch

2. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (145 reviews)
"The room was really nice and the breakfast was great."
United States
Mark
The price is ₩197,746
₩224,442 total
includes taxes & fees
Aug 23 - Aug 24
Kapp and Kappy B&B
Pool

3. 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 ₩56,254
₩158,438 total
includes taxes & fees
Aug 21 - Aug 22
The Gathering Place
Design Room | Living area

4. 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 ₩222,080
₩1,012,679 total
includes taxes & fees
Aug 22 - Aug 23
The Tiny Cottage in The Springs
Exterior

5. 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 ₩74,173
₩160,858 total
includes taxes & fees
Aug 21 - Aug 22
Styled Bedrooms in a Resort
Exterior

6. Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is ₩811,315
₩1,326,651 total
includes taxes & fees
Aug 23 - Aug 24
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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent
"amazing room and close to disney! the community here is amazing and the entire front desk staff were extremely nice and accommodating!!! will definitely be staying here again!"
Caitlin 4-night trip
Posted less than an hour ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Find out more about Windermere

Windermere B&B information

Number of reviews
36
Accommodation
7 B&B
Lowest Price
₩158,438
Highest Price
₩1,326,651

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?
Below are some B&Bs in the area: Kapp and Kappy B&B: 3 rooms. 15.9 mi (25.5 km) from the heart of Windermere. Enjoy the free full breakfast and unique décor. Hotel Styled Bedrooms in a Villa: 4 rooms. 14.7 mi (23.6 km) from the downtown core. 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 put Isleworth Golf and Country Club and Lake Bessie on your list if you want 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.