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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Windermere bed & breakfast

Porch
Kapp and Kappy B&B

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (125)
"Friendly host. Felt like home. "
Canada
Gordon
The price is AU$261
includes taxes & fees
18 Jan - 19 Jan 2026
Kapp and Kappy B&B
Design Room | Living area
The Tiny Cottage in The Springs

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)
"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 AU$1,014
includes taxes & fees
4 Jan - 5 Jan 2026
The Tiny Cottage in The Springs
Outdoor pool
Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
6.0 out of 10, (6)
"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 AU$175
includes taxes & fees
2 Jan - 3 Jan 2026
Hotel Styled Bedrooms in a Villa
Shared kitchen
The Gathering Place

The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
2.0 out of 10, (1)
"Not to clean or to friendly "
United States
Tier
The price is AU$89
includes taxes & fees
30 Jan - 31 Jan 2026
The Gathering Place
Outdoor pool
Styled Bedrooms in a Resort

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
3.0 out of 10, (2)
"Uncleanliness "
United States
Gina
The price is AU$182
includes taxes & fees
29 Jan - 30 Jan 2026
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

Find out more about Windermere

Windermere B&B information

Number of reviews
134
Accommodation
27 B&B
Lowest Price
AU$89
Highest Price
AU$1,014

Frequently asked questions

Searching for B&Bs in Windermere?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your holiday. If you're interested in playing some golf on your trip, Isleworth Golf and Country Club is a good spot to get in a game.
Are you thinking about apartments over traditional hotel rooms?
With attentive service, an atmosphere suited to mingling with other guests and breakfast served on site, B&Bs provide a unique environment.
What are the best B&Bs in Windermere?
Below are some B&Bs in the surrounding 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 decor. Hotel Styled Bedrooms in a Villa: 4 rooms. 14.7 mi (23.6 km) from the city centre. Oakland Manor House: 5 rooms. Situated 7.2 mi (11.6 km) from the heart of Windermere. Styled Bedrooms in a Resort: 6 rooms. 18.4 mi (29.7 km) from the city centre. ORLANDO Blue Heron Condo 1 Mile From Disney 11th floor - 8: Located 9 mi (14.5 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 stay in Windermere, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Windermere are August, July, September and June, with each month seeing an average of 194 mm 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 could visit 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 International Airport (MCO), which is located 14.5 mi (23.3 km) away from the city centre. 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, you may want to rent a car for your trip.

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