Search Guest Houses in Windermere from CA $142

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Check prices for these dates

Next weekend
May 8 - May 10
In two weeks
May 15 - May 17
In one month
May 29 - May 31
In two months
Jun 26 - Jun 28

Our top choices for Windermere guest houses

Outdoor pool, a heated pool

Historic lakefront guesthouse

Historic lakefront guesthouse
Orlando
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful and well kept property. Worth the visit!"
United States
Jason B.
The price is CA $136
CA $432 total
includes taxes & fees
May 11 - May 12
Historic lakefront guesthouse
Interior

Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (183 reviews)
"This was a great place to stay. Bunker, his son, and Alexia were very nice and accommodating. We had a great time! Will definitely stay here on my next trip to Orlando"
United States
Domingo
The price is CA $110
CA $260 total
includes taxes & fees
May 11 - May 12
Quiet Oasis in Lovely Neighborhood
Private kitchen

SmartStay Homes

SmartStay Homes
2.0 star property
Kissimmee
The price is CA $84
CA $203 total
includes taxes & fees
May 6 - May 7
SmartStay Homes
Hallway

Enchanted Fantasy

Enchanted Fantasy
2.0 star property
Kissimmee
8.6 out of 10, Excellent, (8 reviews)
"The carpet in the bedroom was lightly stained, but it smelled like it was shampooed before my stay. The bed was very comfortable. The linens and mattress smelled freshly laundered. Super hot strong shower was a plus. Overall, the experience was really great and the host was accommodating. Will rent again. "
United States
Robert
The price is CA $58
CA $158 total
includes taxes & fees
May 18 - May 19
Enchanted Fantasy
Dining

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

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Buena Ventura Lakes
The price is CA $110
CA $287 total
includes taxes & fees
May 1 - May 2
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Outdoor pool

Tempo Trek Lodgings

Tempo Trek Lodgings
3.0 star property
Solterra Resort
7.2 out of 10, Good, (36 reviews)
"Love the area "
United States
Jahbari
The price is CA $45
CA $142 total
includes taxes & fees
May 9 - May 10
Tempo Trek Lodgings
Smart TV

Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED
Downtown Orlando
9.2 out of 10, Wonderful, (50 reviews)
"Great location - nice, clean apartment"
United States
Richard W.
The price is CA $118
CA $256 total
includes taxes & fees
Apr 30 - May 1
Downtown Lake Eola Historic House 1 OR 2 BED
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful grounds and awesome amenities."
United States
Serenity C.
The price is CA $220
CA $501 total
includes taxes & fees
Apr 29 - Apr 30
Mills Cottage by the Little Lake
Interior entrance

Jade Manor

Jade Manor
2.0 star property
Solterra Resort
7.0 out of 10, Good, (8 reviews)
"We had an amazing stay! The home was clean, comfortable, and exactly as described. The host was responsive and welcoming, which made everything even better. We truly enjoyed our time and would definitely stay here again!"
United States
Brittani
The price is CA $69
CA $169 total
includes taxes & fees
Apr 29 - Apr 30
Jade Manor
Outdoor pool

Magical Dreams

Magical Dreams
3.0 star property
Kissimmee
5.8 out of 10, (20 reviews)
"Overall was a good stay . "
United States
Sorina
The price is CA $72
CA $174 total
includes taxes & fees
Apr 29 - Apr 30
Magical Dreams
Full-size fridge, microwave, oven, stovetop

Leisure Lounge

Leisure Lounge
3.0 star property
Solterra Resort
7.8 out of 10, Good, (24 reviews)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is CA $61
CA $160 total
includes taxes & fees
May 1 - May 2
Leisure Lounge
2 outdoor pools

Oasis Private Ensuite Room Shared Home

Oasis Private Ensuite Room Shared Home
2.0 star property
Kissimmee
4.0 out of 10, (4 reviews)
"I was switch to a different location the day before arriving. The new location had roaches! And it should be noted before booking about the $60 a day fee to heat the pool. Ruined my whole trip not being able to swim! There was mention of a clubhouse to swim but it wasn’t in walking distance."
United States
Latisha
The price is CA $78
CA $189 total
includes taxes & fees
May 29 - May 30
Oasis Private Ensuite Room Shared Home
50-inch Smart TV with digital channels

Enchanted Dreams

Enchanted Dreams
3.0 star property
Kissimmee
4.8 out of 10, (15 reviews)
"Very relaxing space. Clean environment. Coming back very soon "
United States
Tanish
The price is CA $81
CA $185 total
includes taxes & fees
Apr 29 - Apr 30
Enchanted Dreams
Quadruple Room, 2 Queen Beds, Non Smoking, Private Bathroom

Harmony Haven

Harmony Haven
2.0 star property
Kissimmee
3.0 out of 10, (2 reviews)
"It was loud and more like a rooming house there was a baby there who cried all the time I didn’t stay the last night we went so where else"
United States
Ciera
The price is CA $61
CA $162 total
includes taxes & fees
Apr 30 - May 1
Harmony Haven
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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Such a lovely hotel, friendly staff, lots to do. Pool was a little chilly though."
Simon 7-night trip
Posted 1 hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Windermere

Windermere Guest Houses information

Number of reviews
401
Accommodation
46 Guest Houses
Lowest Price
CA $142
Highest Price
CA $501

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 $142 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.

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