A lakeside community with houses and boats.

Find a Bed and Breakfast in Windermere from CA $152

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Our top choices for Windermere bed & breakfast

Cozy 1-bedroom with AC in awesome Winter Garden

Cozy 1-bedroom with AC in awesome Winter Garden
Winter Garden
The price is CA $180
CA $513 total
includes taxes & fees
Aug 16 - Aug 17
Cozy 1-bedroom with AC in awesome Winter Garden

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (142 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 $220
CA $250 total
includes taxes & fees
Aug 16 - Aug 17
Kapp and Kappy B&B

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 CA $71
CA $176 total
includes taxes & fees
Jul 24 - Jul 25
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 $70
CA $175 total
includes taxes & fees
Jul 27 - Jul 28
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 $224
CA $1,022 total
includes taxes & fees
Jul 21 - Jul 22
The Tiny Cottage in The Springs

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 $66
CA $152 total
includes taxes & fees
Aug 9 - Aug 10
Styled Bedrooms in a Resort

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is CA $811
CA $1,330 total
includes taxes & fees
Jul 23 - Jul 24
Oakland Manor House

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
Clermont
9.6 out of 10, Exceptional, (5 reviews)
"Very beautiful property and friendly owners we had an awesome time staying here! "
United States
Angel P.
The price is CA $227
CA $452 total
includes taxes & fees
Aug 18 - Aug 19
PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

Mario-Themed Hotel Room • 2 Queen Beds •

Mario-Themed Hotel Room • 2 Queen Beds •
Kissimmee
The price is CA $81
CA $203 total
includes taxes & fees
Jul 21 - Jul 22
Mario-Themed Hotel Room • 2 Queen Beds •

Superhero Hotel Room • 2 Queen Beds • Near Disney

Superhero Hotel Room • 2 Queen Beds • Near Disney
Kissimmee
The price is CA $81
CA $203 total
includes taxes & fees
Jul 21 - Jul 22
Superhero Hotel Room • 2 Queen Beds • Near Disney
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

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Windermere B&B information

Number of reviews
182
Accommodation
29 B&B
Lowest Price
CA $152
Highest Price
CA $1,330

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. Styled Bedrooms in a Resort: 6 rooms. 18.4 mi (29.7 km) from the heart of downtown.The Tiny Cottage in The Springs: 2 rooms. Located 16.5 mi (26.6 km) from the core of Windermere. Enjoy the unique décor and fireplace in the lobby.
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.

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