A lakeside community with houses and boats.

Find a Bed and Breakfast in Windermere from CA $158

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Windermere bed & breakfast

A modern interior with a curved sectional sofa, a round coffee table with a plant, and a brick wall.

1. Cozy 1-bedroom with AC in awesome Winter Garden

Cozy 1-bedroom with AC in awesome Winter Garden
Winter Garden
The price is CA $178
CA $506 total
includes taxes & fees
Sep 7 - Sep 8
Cozy 1-bedroom with AC in awesome Winter Garden
A rectangular swimming pool with a hot tub, surrounded by a brick patio and palm trees.

2. Tempo Room Lodgings

Tempo Room Lodgings
3.0 star property
Kissimmee
The price is CA $68
CA $171 total
includes taxes & fees
Sep 16 - Sep 17
Tempo Room Lodgings
A covered porch with wooden chairs and a ceiling fan.

3. 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 CA $205
CA $233 total
includes taxes & fees
Sep 29 - Sep 30
Kapp and Kappy B&B
A bedroom with a bed, a desk with a chair, a ceiling fan, a TV on the wall, and a window with blinds.

4. Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood

Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood
Orlando
The price is CA $156
CA $203 total
includes taxes & fees
Sep 10 - Sep 11
Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood
A pool area with a clear view of the surrounding buildings, a blue inflatable shark, and several lounge chairs.

5. 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 $72
CA $176 total
includes taxes & fees
Sep 7 - Sep 8
Hotel Styled Bedrooms in a Villa
A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

6. 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 $56
CA $158 total
includes taxes & fees
Sep 7 - Sep 8
The Gathering Place
A modern living room with a white sofa, a dining table with chairs, a fireplace, and a staircase leading to an upper level.

7. 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 $184
CA $968 total
includes taxes & fees
Sep 14 - Sep 15
The Tiny Cottage in The Springs
A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

8. 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 CA $74
CA $160 total
includes taxes & fees
Sep 7 - Sep 8
Styled Bedrooms in a Resort
A cozy room with a sofa, armchair, and a small table, large windows with a view of the parking lot, and a ceiling with hanging plants.

9. 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 $237
CA $461 total
includes taxes & fees
Sep 7 - Sep 8
PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Great location and amenities"
Sheena 4-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Windermere

Windermere B&B information

Number of reviews
36
Accommodation
12 B&B
Lowest Price
CA $158
Highest Price
CA $968

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. Cozy 1-bedroom with AC in awesome Winter Garden: Situated 5.6 mi (9 km) from the heart of Windermere. PrivateOakForest RanchFirepit, BBQ&FamilyRetreat: 17.3 mi (27.8 km) from the heart of downtown. The Gathering Place: Located 14.6 mi (23.6 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.

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