A lakeside community with houses and boats.

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Windermere bed & breakfast

A hotel room with a large bed, a nightstand, and a headboard.

1. Tempo Room Lodgings

Tempo Room Lodgings
3.0 star property
Kissimmee
$104 nightly
The price is $118
Oct 28 - Oct 29
Total with taxes and fees
Tempo Room Lodgings
A covered porch with wooden chairs and a ceiling fan.

2. Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (147 reviews)
"An amazing experience. Freindly hosts. If we go to Orlando again we will rwbook"
United States
THOMAS
$164 nightly
The price is $186
Oct 26 - Oct 27
Total with taxes and fees
Kapp and Kappy B&B
A pool area with a clear view of the surrounding buildings, a blue inflatable shark, and several lounge chairs.

3. 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
$120 nightly
The price is $136
Oct 26 - Oct 27
Total with taxes and fees
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.

4. 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
$109 nightly
The price is $123
Nov 24 - Nov 25
Total with taxes and fees
The Gathering Place
A swimming pool with a hot tub, surrounded by a covered patio area with chairs and a grill.

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

Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood
Orlando
$145 nightly
The price is $161
Oct 29 - Oct 30
Total with taxes and fees
Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood
A modern living room with a white sofa, a dining table with chairs, a fireplace, and a staircase leading to an upper level.

6. 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
$694 nightly
The price is $717
Nov 25 - Nov 26
Total with taxes and fees
The Tiny Cottage in The Springs
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.

7. PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
Clermont
9.8 out of 10, Exceptional, (8 reviews)
"Very beautiful property and friendly owners we had an awesome time staying here! "
United States
Angel P.
$302 nightly
The price is $331
Oct 27 - Oct 28
Total with taxes and fees
PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
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
$110 nightly
The price is $123
Oct 27 - Oct 28
Total with taxes and fees
Styled Bedrooms in a Resort
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
"I've stayed here every time I've come to Florida so far. I greatly appreciate how kind and helpful the staff are here, as well as the amenities included. While I did spend most of the day out of the hotel, it's good to know that breakfast is included and that there are water stations here and a gym. I look forward to the next stay here."
Ka Yung 4-night trip
Posted 7 hours 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
191
Accommodation
12 B&B
Lowest Price
$118
Highest Price
$717

Frequently asked questions

What is the nightly rate for a B&B in Windermere?
Prices for B&Bs in Windermere often vary, but you can find a great deal from $118 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windermere B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Windermere?
The most popular time to book a B&B in Windermere is from July to September, when the area comes alive with outdoor enthusiasts seeking the stunning landscapes and recreational activities that this beautiful region offers. During these peak months, visitors can enjoy warm temperatures averaging in the mid-70s to low 80s Fahrenheit, making it ideal for hiking, boating, and exploring the charming local attractions.

July stands out as the busiest month, with an array of festivals and events drawing crowds from near and far. Adventurers can take advantage of the long, sunny days to experience everything from tranquil boat rides on the lake to invigorating hikes along scenic trails that overlook breathtaking vistas.

For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, superb for enjoying the tranquility of the area while still taking in the beautiful fall foliage. Crisp autumn air presents an excellent opportunity for leisurely walks and cozy evenings by the fireplace.
What is the difference between a Windermere Bed and Breakfast and a hotel?
Every Windermere B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windermere B&Bs.

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