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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured B&B in Windermere

Edgewater Hotel
Surrounded by lush greenery and vibrant flowers, the EDGE WATER HOTEL offers a serene and inviting atmosphere.

Edgewater Hotel

2.5 star property
9.6 out of 10, Exceptional, (310)
"Great place to stay. Good and easily accessible. Staff was amazing!"
The price is AU$242
includes taxes & fees
6 Aug - 7 Aug
Edgewater Hotel
Kapp and Kappy B&B
Relax on the porch with comfortable seating and enjoy the serene surroundings.

Kapp and Kappy B&B

3.5 star property
9.8 out of 10, Exceptional, (121)
"Only B&B in Kissimmee. Owners were excellent. Enjoyed talking to them each morning over a great breakfast. Would definitely go back. "
The price is AU$264
includes taxes & fees
17 Aug - 18 Aug
Kapp and Kappy B&B
Hotel Styled Bedrooms in a Villa
Relax by the pool surrounded by lounge chairs and a separate kiddie 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$198
includes taxes & fees
5 Aug - 6 Aug
Hotel Styled Bedrooms in a Villa
Oakland Manor House
Staircase leads to an upper level with framed pictures on the walls.

Oakland Manor House

3.0 star property
Oakland Manor House
The Tiny Cottage in The Springs
Cozy living space with a dining area, seating area, and kitchenette.

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$1,049
includes taxes & fees
31 Aug - 1 Sept
The Tiny Cottage in The Springs
Luxury Home Near Disney sleeps 20
Relax by the pool surrounded by palm trees and lounge chairs.

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.
Enjoy cooking and dining in this well-equipped kitchen with a central island and stainless steel appliances.

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.
Charming 2-bedroom bed & breakfast in beautiful Orlando with WiFi, AC
Bar (on property)

Charming 2-bedroom bed & breakfast in beautiful Orlando with WiFi, AC

Charming 2-bedroom bed & breakfast in beautiful Orlando with WiFi, AC
Disney Vacation Home
Relax in this spacious living area with a mezzanine level, featuring a large sectional sofa, ottoman, and flat-screen TV.

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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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: Edgewater Hotel: 15 rooms. 5.8 mi (9.3 km) from the heart of Windermere. Enjoy the free cooked breakfast and snack bar/deli. Kapp and Kappy B&B: 3 rooms. 15.9 mi (25.5 km) from the city centre. Enjoy the free full breakfast and unique decor. Hotel Styled Bedrooms in a Villa: 4 rooms. Situated 14.7 mi (23.6 km) from the heart of Windermere. Oakland Manor House: 5 rooms. 7.2 mi (11.6 km) from the city centre. The Tiny Cottage in The Springs: 2 rooms. Located 16.5 mi (26.6 km) from the core of Windermere. Enjoy the unique decor and fireplace in reception.
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.