Find a Bed and Breakfast in Windermere from CA $153

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Our top choices for Windermere 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, (140 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 CA $196
CA $222 total
includes taxes & fees
Jun 4 - Jun 5
Kapp and Kappy B&B

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 CA $67
CA $153 total
includes taxes & fees
Jun 7 - Jun 8
Styled Bedrooms in a Resort

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 CA $68
CA $171 total
includes taxes & fees
Jun 6 - Jun 7
Hotel Styled Bedrooms in a Villa

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 CA $69
CA $172 total
includes taxes & fees
Jun 6 - Jun 7
The Gathering Place

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 CA $221
CA $1,009 total
includes taxes & fees
Jun 9 - Jun 10
The Tiny Cottage in The Springs

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
Clermont
9.4 out of 10, Exceptional, (3 reviews)
"Very beautiful property and friendly owners we had an awesome time staying here! "
United States
Angel P.
The price is CA $237
CA $461 total
includes taxes & fees
Jun 5 - Jun 6
PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is CA $772
CA $1,281 total
includes taxes & fees
Jun 11 - Jun 12
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

Find out more about Windermere

Windermere B&B information

Number of reviews
180
Accommodation
29 B&B
Lowest Price
CA $153
Highest Price
CA $1,281

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: Situated 14.6 mi (23.6 km) from the heart of Windermere. The Tiny Cottage in The Springs: 2 rooms. 16.5 mi (26.6 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby. PrivateOakForest RanchFirepit, BBQ&FamilyRetreat: Located 17.3 mi (27.8 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.

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