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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 9 B&B in Windermere with updated reviews, rates, and availability.

Edgewater Hotel
City view from property

Edgewater Hotel

2.5 star property
9.6 out of 10, Exceptional, (297)
"Excellent location, great breakfast, staff was very friendly and helpful. Only downside was you had to call the staff to use the elevator. However they responded quickly. "
The price is AED 494
AED 555 total
includes taxes & fees
6 Apr - 7 Apr
Edgewater Hotel
Kapp and Kappy B&B
Porch

Kapp and Kappy B&B

3.5 star property
9.8 out of 10, Exceptional, (115)
"Fun B&B for an older couple traveling to the Kissimmee area. Good value for the price. The owners are fun and interesting and we enjoyed talking to them over breakfast. The facilities were dated but clean and in good working order. The window coverings did not fully cover the Windows which may be an issue if you are doing clothing-optional activities in the room. The Down pillows were also very flat. Overall we liked it and would stay there again."
The price is AED 596
AED 676 total
includes taxes & fees
16 Mar - 17 Mar
Kapp and Kappy B&B
1 BDR, 1BA in gated community with pool/playground access
Outdoor pool

1 BDR, 1BA in gated community with pool/playground access

9.8 out of 10, Exceptional, (42)
"Very responsive and kind!"
1 BDR, 1BA in gated community with pool/playground access
Hotel Styled Bedrooms in a Villa
Outdoor pool

Hotel Styled Bedrooms in a Villa

3.0 star property
5.6 out of 10, (4)
"I didn’t know it was a house being shared by like 6 other tenants and parking was a pain"
The price is AED 162
AED 434 total
includes taxes & fees
1 Apr - 2 Apr
Hotel Styled Bedrooms in a Villa
The Tiny Cottage in The Springs
Design Room | Living area | 40-inch Smart TV with digital channels, TV

The Tiny Cottage in The Springs

4.0 star property
9.8 out of 10, Exceptional, (26)
"There are actually so many nice things to say about this place. The host is super kind and always available. The place is beautifully decorated with everything you might need even an iron hair dryer. I am very sensitive to scented items and there are no harsh chemicals or scents. Even the soaps and lotions she provides are not overly scented. I was surprised to learn there was a cleaning fee but it’s only $25 which seems fair. Your stay here will inspire you to consider building your own tiny...
The price is AED 555
AED 2,457 total
includes taxes & fees
9 Mar - 10 Mar
The Tiny Cottage in The Springs
Luxury Home Near Disney sleep 20
Outdoor pool, a heated pool

Luxury Home Near Disney sleep 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 sleep 20
Student room near UCF. 1200/month or 75+ site fees.
Miscellaneous

Student room near UCF. 1200/month or 75+ site fees.

10.0 out of 10, Exceptional, (9)
"very communicative. very clean. enjoyable great stay! 10/10 recommend! convient safe location. he was great and so very nice!!"
The price is AED 312
AED 425 total
includes taxes & fees
8 Mar - 9 Mar
Student room near UCF. 1200/month or 75+ site fees.
Chilled Spot the perfect hide away.
Interior

Chilled Spot the perfect hide away.

10.0 out of 10, Exceptional, (3)
"The place was nicely decorated, great kitchen. Only 5 places to sit but we had 2 staying and 2 visitors so it was ok. Back yard is pretty small but good enough although the sofa is in front of the back door, so some maneuvering was required."
Chilled Spot the perfect hide away.
Oakland Manor House
Porch

Oakland Manor House

2.0 star property
The price is AED 2,295
AED 2,582 total
includes taxes & fees
7 Mar - 8 Mar
Oakland Manor House
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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Other property types in Windermere

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1653)
"Everything was perfect "
The price is AED 306
AED 403 total
includes taxes & fees
19 Mar - 20 Mar
Vacation Village at Parkway
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8401)
"Very convenient. Close to the parks. Good parking. Kids loved the pool. Friendly staff. "
Lake Buena Vista Resort Village & Spa
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1236)
"We loved so much about the stay, the cottages were modern but comfortable and smartly decorated. There were all the essentials in the kitchen even a huge amazing blender. The buildings were very attractive and painted lovely colors. Beds were comfortable and bathrooms as well (could have been a little more upgraded, basic shower stalls). The entire unit was very spacious also. The pools were gorgeous with chairs available right in front. However there were a few things we didn't like. We were...
Margaritaville Resort Orlando Cottages by Rentyl
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.

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: Edgewater Hotel: 15 rooms. 5.8 mi (9.3 km) from the heart of Windermere. Enjoy the free cooked breakfast and deli. Hotel Styled Bedrooms in a Villa: 4 rooms. 14.7 mi (23.6 km) from the downtown core. Kapp and Kappy B&B: 3 rooms. Situated 15.9 mi (25.5 km) from the heart of Windermere. Enjoy the free full breakfast and unique décor. Luxury Home Near Disney sleep 20: 13 mi (21 km) from the heart of downtown. Enjoy the in-room pools and fitness center. The Tiny Cottage in The Springs: 2 rooms. Located 16.5 mi (26.6 km) from the core of Windermere. Enjoy the unique décor and fireplace in the lobby.
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 check out 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 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.