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Our top choices for Windermere bed & breakfast

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)
"Great place. Comfy and personable. Won’t stay anywhere else while in the area. "
United States
Nelson
Kapp and Kappy B&B

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 165
SAR 443 total
includes taxes & fees
17 Mar - 18 Mar
Hotel Styled Bedrooms in a Villa

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

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 2,548 total
includes taxes & fees
13 Mar - 14 Mar
The Tiny Cottage in The Springs

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 1,112 total
includes taxes & fees
30 Mar - 31 Mar
3-Bedroom House with Fire Pit, Volleyball & Tree nature’s for family and friends

Banana Leaf Villa-Marley Suite with Living Room

Banana Leaf Villa-Marley Suite with Living Room
Orlovista
The price is SAR 326
SAR 440 total
includes taxes & fees
5 Apr - 6 Apr
Banana Leaf Villa-Marley Suite with Living Room

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
11 Apr - 12 Apr
The Gathering Place

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 187
SAR 419 total
includes taxes & fees
20 Mar - 21 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

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. Chilled Spot the perfect hide away.: Situated 17.8 mi (28.6 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 Gathering Place: Located 14.6 mi (23.6 km) from the core of Windermere.
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.