A lakeside community with houses and boats.

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Check prices for these dates

Next weekend
10 July - 12 July
In two weeks
17 July - 19 July
In one month
31 July - 2 Aug
In two months
28 Aug - 30 Aug

Our top choices for Windermere bed & breakfast

Exterior

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
4.6 out of 10, (4 reviews)
"I was very comfortable with the people that were staying there. Very nice place. Would recommend anyone to stay."
United States
Jason
The price is AU$160
includes taxes & fees
7 July - 8 July
Styled Bedrooms in a Resort
Porch

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (142 reviews)
"Our first experience with a B&B - but won't be our last! Very cute and unique house and the host makes a great breakfast! Everything provided that you might need - including some drinks and snacks! Nice to be able to visit and get suggestions from someone who knows the area."
United States
Laura
The price is AU$237
includes taxes & fees
7 July - 8 July
Kapp and Kappy B&B
Outdoor pool

The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
5.0 out of 10, (2 reviews)
"clean room and bathroom"
United States
Matthew
The price is AU$175
includes taxes & fees
7 July - 8 July
The Gathering Place
Outdoor pool

Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
5.8 out of 10, (8 reviews)
"Parking was almost a mile away. Didn’t even get to stay there and wasted over $200 on the stay. Communication was bad. I tried to get a refund because of the parking situation, they never got back to me. "
United States
Chantal
The price is AU$181
includes taxes & fees
8 July - 9 July
Hotel Styled Bedrooms in a Villa
Design Room | Living area

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 AU$1,051
includes taxes & fees
6 July - 7 July
The Tiny Cottage in The Springs
Exterior

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is AU$1,338
includes taxes & fees
23 July - 24 July
Oakland Manor House
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Awesome location to use when travelling in or out of Orlando. We stay here often."
Jacob 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

Find out more about Windermere

Windermere B&B information

Number of reviews
182
Accommodation
33 B&B
Lowest Price
AU$160
Highest Price
AU$1,338

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?
Here are some B&Bs in the area: PrivateOakForest RanchFirepit, BBQ&FamilyRetreat: 17.3 mi (27.8 km) from the heart of Windermere. 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. The Gathering Place: 14.6 mi (23.6 km) from the city centre. Styled Bedrooms in a Resort: 6 rooms. Located 18.4 mi (29.7 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 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 should put Isleworth Golf and Country Club and Lake Bessie on your list if you want 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.

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