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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured B&B in Windermere

Kapp and Kappy B&B
Porch

Kapp and Kappy B&B

3.5 star property
9.8 out of 10, Exceptional, (123)
"It was perfect for us. The hosts were very friendly and accommodating. They just opened a brewery downtown that we were able to walk to, and we had a great time there as well. Overall a great B&B."
The price is AU$297
includes taxes & fees
20 Aug - 21 Aug
Kapp and Kappy B&B
Hotel Styled Bedrooms in a Villa
Outdoor pool

Hotel Styled Bedrooms in a Villa

3.0 star property
5.6 out of 10, (5)
"bad parking quiet hour not observed"
The price is AU$196
includes taxes & fees
18 Aug - 19 Aug
Hotel Styled Bedrooms in a Villa
Oakland Manor House
Staircase

Oakland Manor House

3.0 star property
Oakland Manor House
The Tiny Cottage in The Springs
Design Room | Living area

The Tiny Cottage in The Springs

4.0 star property
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."
The price is AU$1,044
includes taxes & fees
31 Aug - 1 Sept
The Tiny Cottage in The Springs
Luxury Home Near Disney sleeps 20
Outdoor pool, a heated pool

Luxury Home Near Disney sleeps 20

10.0 out of 10, Exceptional, (1)
"We all enjoyed the space & comfort of the house. Beds and linens were very comfortable with plenty of seating area for a large group. Neighborhood was very quiet and pool area was great for relaxing in the evenings when the sun went down. Our golfers loved the four golf courses near by. Owner was readily available (though we had no issues). We were enjoying spending time with our family so didn’t really make use of the movie room or the huge TV. Recommended for large groups."
Luxury Home Near Disney sleeps 20
Chilled Spot the perfect hide away.
Interior

Chilled Spot the perfect hide away.

10.0 out of 10, Exceptional, (3)
"Property managers were extremely courteous and had great communication. The home was very clean. This residential area was exactly what we wanted- close enough to access everything but also quiet enough to feel like home. Parking is limited but we had no problem with it. It was a great stay for us! "
Chilled Spot the perfect hide away.
Disney Vacation Home
Living area

Disney Vacation Home

Disney Vacation Home
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Darnell and Kaya was very helpful I was having issues with adding my Disney tickets to apple wallet and they help, the breakfast was very good also the check out staff was very nice."
Naresh 2-night trip
Posted 12 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

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. The Tiny Cottage in The Springs: 2 rooms. 16.5 mi (26.6 km) from the city centre. Enjoy the unique decor and fireplace in reception. Luxury Home Near Disney sleeps 20: Located 13 mi (21 km) from the core of Windermere. Enjoy the in-room pools and fitness centre.
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.