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Check prices for these dates

Next weekend
20 Mar - 22 Mar
In two weeks
27 Mar - 29 Mar
In one month
10 Apr - 12 Apr
In two months
8 May - 10 May

Our top choices for Windermere bed & breakfast

Porch

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (134 reviews)
"Wonderful host! We really enjoyed our stay and would most definitely return."
United States
Stephanie Lynne
Kapp and Kappy B&B
TV, offices

Banana Leaf Villa-Vintage Vibes Premium Room

Banana Leaf Villa-Vintage Vibes Premium Room
Orlovista
8.0 out of 10, Very Good, (4 reviews)
"This is the perfect getaway spot! Very accessible, quiet area. I will definitely be booking again."
United States
Keisha
The price is SAR 364
SAR 482 total
includes taxes & fees
16 Mar - 17 Mar
Banana Leaf Villa-Vintage Vibes Premium Room
Outdoor pool

Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
6.4 out of 10, (7 reviews)
"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 SAR 166
SAR 443 total
includes taxes & fees
1 Apr - 2 Apr
Hotel Styled Bedrooms in a Villa
Design Room | Living area | 40-inch Smart TV with digital channels, TV

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 reviews)
"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 SAR 600
SAR 2,549 total
includes taxes & fees
11 Mar - 12 Mar
The Tiny Cottage in The Springs
Smart TV

3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends

3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends
Clermont
10.0 out of 10, Exceptional, (1 review)
"Sych a cute, comfy and cozy place to stay. The host was very nice and accommodating, and answered all of my questions in a timely manner. "
United States
Tera S.
The price is SAR 537
SAR 1,113 total
includes taxes & fees
30 Mar - 31 Mar
3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends
TV, offices

Banana Leaf Villa-Marley Suite with Living Room

Banana Leaf Villa-Marley Suite with Living Room
Orlovista
The price is SAR 327
SAR 440 total
includes taxes & fees
12 Mar - 13 Mar
Banana Leaf Villa-Marley Suite with Living Room
Outdoor pool

The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
2.0 out of 10, (1 review)
"Not to clean or to friendly "
United States
Tier
The price is SAR 203
SAR 486 total
includes taxes & fees
8 Apr - 9 Apr
The Gathering Place
Exterior

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
2.8 out of 10, (3 reviews)
"Uncleanliness "
United States
Gina
The price is SAR 203
SAR 437 total
includes taxes & fees
11 Mar - 12 Mar
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

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"I really enjoy my stay. Rooms were clean and comfortable. "
Maryssa 2-night trip
Posted less than an hour ago
Vacation Village Orlando, Celebration

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. Hotel Styled Bedrooms in a Villa: 4 rooms. 14.7 mi (23.6 km) from the downtown core. The Gathering Place: Situated 14.6 mi (23.6 km) from the heart of Windermere. 3-Bedroom House with Fire Pit, Volleyball & Tree nature's for family and friends: 17.3 mi (27.8 km) from the heart of downtown. 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.