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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 10 B&B in Windermere with updated reviews, rates, and availability.

Kapp and Kappy B&B
Porch

Kapp and Kappy B&B

3.5 star property
9.8 out of 10, Exceptional, (117)
"This place was immaculate and convenient and comfortable. It was a great place to enjoy. Also a great breakfast before you check out!"
The price is AED 596
AED 676 total
includes taxes & fees
7 Apr - 8 Apr
Kapp and Kappy B&B
Edgewater Hotel
City view from property

Edgewater Hotel

2.5 star property
9.6 out of 10, Exceptional, (302)
"Very unique property. Old 1920's hotel in downtown Winter Garden that's been renovated. Staff was very nice and helpful. Cooked to order breakfast is outstanding. The breakfast area is open throughout the rest of the day for self-serve snacks at no extra charge. Easy parking."
The price is AED 523
AED 588 total
includes taxes & fees
15 Apr - 16 Apr
Edgewater Hotel
Hotel Styled Bedrooms in a Villa
Outdoor pool

Hotel Styled Bedrooms in a Villa

3.0 star property
5.6 out of 10, (5)
"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
20 Apr - 21 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 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 257
AED 363 total
includes taxes & fees
7 Apr - 8 Apr
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 2,296
AED 2,583 total
includes taxes & fees
14 Apr - 15 Apr
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, (1907)
"Perfect spot and location for my son and I to take a quick weekend trip. "
The price is AED 327
AED 434 total
includes taxes & fees
20 Apr - 21 Apr
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, (8532)
"Overall nice place "
The price is AED 493
AED 663 total
includes taxes & fees
7 Apr - 8 Apr
Lake Buena Vista Resort Village & Spa
Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5318)
"We really enjoyed our stay at Summer Bay Orlando. The room seemed pretty new and was very clean. Pools and hot tubs were open late which was a plus as well. They were a bit pushy about getting you to do their time share pitch, but otherwise really great. "
The price is AED 426
AED 595 total
includes taxes & fees
7 Apr - 8 Apr
Summer Bay Orlando by Exploria Resorts
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: 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 décor. Edgewater Hotel: 15 rooms. 5.8 mi (9.3 km) from the downtown core. Enjoy the free cooked breakfast and deli. Hotel Styled Bedrooms in a Villa: 4 rooms. Situated 14.7 mi (23.6 km) from the heart of Windermere. The Tiny Cottage in The Springs: 2 rooms. 16.5 mi (26.6 km) from the heart of downtown. Enjoy the unique décor and fireplace in the lobby. Luxury Home Near Disney sleep 20: Located 13 mi (21 km) from the core of Windermere. Enjoy the in-room pools and fitness center.
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.