Search Guest Houses in Windermere from CA $81

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Sep 19 - Sep 21
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Nov 7 - Nov 9

Browse Select Windermere Guest Houses

Disney Proximity Escape - Comfort in Kissimmee
Outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas, sun loungers

Disney Proximity Escape - Comfort in Kissimmee

3.0 star property
8.2 out of 10, Very good, (27)
"It was very nice 😊 "
Disney Proximity Escape - Comfort in Kissimmee
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Fridge, microwave, stovetop, coffee/tea maker

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (71)
"Perfect house, perfect location, and the host is very pleasant and easy to get in contact with. A great stay."
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Winter Park Getaway
Outdoor dining

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway
Downtown Orlando Throne Historic Thornton Park
Property grounds

Downtown Orlando Throne Historic Thornton Park

8.4 out of 10, Very good, (5)
"Nice size property great location great host"
The price is CA $106
CA $305 total
includes taxes & fees
Sep 9 - Sep 10
Downtown Orlando Throne Historic Thornton Park
Adorable 1bed 1 bath guest house
Smart TV

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (26)
"The apartment was perfect for us! It was clean and spacious and very well appointed with everything needed for the few days we were here. Samson was very accommodating and even allowed us to check in early. We will definitely stay here again as our daughter will be in law school near by for the next 3 years. "
Adorable 1bed 1 bath guest house
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (46)
"Super charming "
The price is CA $174
CA $443 total
includes taxes & fees
Sep 9 - Sep 10
Mills Cottage by the Little Lake
Historic lakefront guesthouse
Outdoor pool, a heated pool

Historic lakefront guesthouse

10.0 out of 10, Exceptional, (6)
"Had ana amazing time! The owner is very responsive and the place was a total vibe "
The price is CA $128
CA $385 total
includes taxes & fees
Sep 9 - Sep 10
Historic lakefront guesthouse
Downtown Lake Eola Historic House 1 OR 2 BED
Smart TV

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (30)
"Good stay everything that we wanted was in walking distance and it was comfortable"
The price is CA $81
CA $196 total
includes taxes & fees
Sep 9 - Sep 10
Downtown Lake Eola Historic House 1 OR 2 BED
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Interior

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

8.8 out of 10, Excellent, (17)
"One bedroom with comfortable foldout futon in small living room. Small fridge, microwave, kettle were ideal for my stay. "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Outdoor pool

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

The price is CA $112
CA $294 total
includes taxes & fees
Sep 10 - Sep 11
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
2BR Orlando Retreat • Pets + Wi-Fi Near Disney
2 bedrooms, desk, iron/ironing board, free WiFi

2BR Orlando Retreat • Pets + Wi-Fi Near Disney

2.0 star property
2BR Orlando Retreat • Pets + Wi-Fi Near Disney
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Full-size fridge, microwave, oven, stovetop

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Had a lovely visit in Orlando! Easy to find, host is very nice, communicative and helpful! Would definitely stay again"
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
3BR Townhouse at Regal Palms: Pool & Disney Fun
House (3 Bedrooms) | Floor plan

3BR Townhouse at Regal Palms: Pool & Disney Fun

2.0 star property
3BR Townhouse at Regal Palms: Pool & Disney Fun
Private Poolside Guest House In Winter Park/Orlando
A heated pool

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando
Palatial Palms Villa Pool BBQ Resort
Outdoor spa tub

Palatial Palms Villa Pool BBQ Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing property. Comfortable beds, plenty of linen, beautiful pool, & great amenities. I loved the pool side bar area. We ate great food & relaxed in the pool. It has a waterfall & slide, which the kids loved. We did not have time to enjoy all of the amenities but they have a movie theater on site, there is an option for a private rental or you can watchvwhat is playing. They post the movie & viewing times. Basketball, playground & more. My host was very nice & responded quickly to all...
Palatial Palms Villa Pool BBQ Resort
Magic Oasis Villa at Paradise Palms
Outdoor spa tub

Magic Oasis Villa at Paradise Palms

3.0 star property
10.0 out of 10, Exceptional, (1)
"Outstanding customer service from the host. Beautiful home and surrounding area. "
Magic Oasis Villa at Paradise Palms
Blissful Guest House
Full-size fridge, microwave, oven, stovetop

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Cozy Wonderfull Clubhouse Close Disney
Townhome

Cozy Wonderfull Clubhouse Close Disney

2.0 star property
Cozy Wonderfull Clubhouse Close Disney
Tree House
Exterior

Tree House

10.0 out of 10, Exceptional, (1)
"Erik at the beehive treehouse was the best host we’ve had in a while. He met us at the spot and showed us everything we needed to know and even bought flowers as a surprise because I told him it was my wife’s birthday. The treehouse is AMAZING, built with love and you feel it in every detail. Peaceful, serene, and quant. Couldn’t have asked for a better mini vacation spot. Thank you Erik!"
Tree House
Dr. Phillips House
Exterior

Dr. Phillips House

3.0 star property
8.2 out of 10, Very good, (13)
"AWESOME LOCATION AND A GREAT PLACE TO STAY. THE ROOM WAS ABSOLUTELY AMAZING!! NO TURN DOWN OR TOWELS AFTER THE FIRST NIGHT STAY ALTHOUGH IT WAS AT THE BEGINNING OF CORONA."
Dr. Phillips 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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Great friendly staff was very polite and attentive to every thing needed definitely recommend staying here"
Johnathan 6-night trip
Posted 23 hours ago
Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Windermere

Find out more about Windermere

Windermere Guest Houses information

Number of reviews
Accommodation
55 Guest Houses
Lowest Price
CA $81
Highest Price
CA $174

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is the nightly rate for a guest house in Windermere?
Rates for Windermere guest houses vary, but travelers can find great-value prices from CA $81 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Windermere guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Windermere guest house and a B&B?
A guest house in Windermere is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.