A lakeside community with houses and boats.

Search Guest Houses in Windermere from CA $155

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Windermere guest houses

A compact living space with a sofa, armchair, coffee table, TV, and a small kitchen area with a sink and countertop.

1. Downtown Lake Eola Historic House 1 OR 2 BED

Downtown Lake Eola Historic House 1 OR 2 BED
Downtown Orlando
9.4 out of 10, Exceptional, (53 reviews)
"We loved our stay, conveniently close to all the downtown Orlando restaurants, and bars, we enjoyed walking around, definitely recommend it."
United States
Cristina T.
The price is CA $103
CA $229 total
includes taxes & fees
Sep 27 - Sep 28
Downtown Lake Eola Historic House 1 OR 2 BED
A room with a wooden floor, a mounted TV, a door, a trash can, and a vase with dried plants.

2. Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (198 reviews)
"The room was clean. It was close to a lot of the activities we wanted to do. The best part was getting to meet and engage with the owners who are wonderful people."
United States
Andy K.
The price is CA $114
CA $268 total
includes taxes & fees
Sep 28 - Sep 29
Quiet Oasis in Lovely Neighborhood
A bedroom with a bed, a desk, a chair, a dresser, a television, and a door.

3. Suncrest Residence

Suncrest Residence
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Good"
United States
Orel
The price is CA $73
CA $195 total
includes taxes & fees
Oct 25 - Oct 26
Suncrest Residence
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

4. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
9.6 out of 10, Exceptional, (67 reviews)
"Great stay. "
United States
rick s.
The price is CA $228
CA $522 total
includes taxes & fees
Sep 28 - Sep 29
Mills Cottage by the Little Lake
A pool area with lounge chairs, a hot tub, and outdoor furniture.

5. Historic lakefront guesthouse

Historic lakefront guesthouse
Orlando
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, really roomy—perfect for decompressing after a busy week of training. The pool, hot tub, and lake were beautiful, and the location is close to everything.Jason was a great host—easy to communicate with and everything was smooth from start to finish.Easy stay, no stress. Would definitely come back."
United States
STEVE O.
The price is CA $169
CA $477 total
includes taxes & fees
Oct 5 - Oct 6
Historic lakefront guesthouse
A hallway with a wooden console table, a potted plant, and a wall-mounted abstract art piece.

6. Enchanted Fantasy

Enchanted Fantasy
2.0 star property
Kissimmee
6.8 out of 10, (13 reviews)
"It was ok"
United States
Norberto
The price is CA $56
CA $159 total
includes taxes & fees
Oct 9 - Oct 10
Enchanted Fantasy
A modern hallway with a clear glass console table, a decorative mirror, and a vase with flowers.

7. Serenity Dreams

Serenity Dreams
3.0 star property
Solterra Resort
The price is CA $69
CA $180 total
includes taxes & fees
Oct 25 - Oct 26
Serenity Dreams
A modern kitchen with white cabinetry, stainless steel appliances, a central island, and green bar stools.

8. SmartStay Homes

SmartStay Homes
3.0 star property
Kissimmee
7.0 out of 10, Good, (4 reviews)
"The bed was comfortable and the room was clean."
United States
Johntavis
The price is CA $86
CA $209 total
includes taxes & fees
Sep 29 - Sep 30
SmartStay Homes
A water park with slides and a pool area, surrounded by palm trees and lounge chairs.

9. SunnyView Residence

SunnyView Residence
3.0 star property
Solterra Resort
8.0 out of 10, Very good, (1 review)
"I could not find the house because the address is listed incorrectly. There were instructions to take off your shoes or use covering, but when I walked from the bed to the bathroom, my feet got really dirty. There’s a dark entertainment room/foyer with neons lights/decor, a pool table and some other items that led to the rooms and were nonfunctional."
United States
Marilyn
The price is CA $73
CA $192 total
includes taxes & fees
Sep 25 - Sep 26
SunnyView Residence
A room with a black sliding door, a round table with chairs, a bed with a white headboard, and wall art.

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

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Buena Ventura Lakes
The price is CA $127
CA $313 total
includes taxes & fees
Oct 17 - Oct 18
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
A covered outdoor area with a pool, lounge chairs, and a hot tub.

11. Tempo Trek Lodgings

Tempo Trek Lodgings
3.0 star property
Solterra Resort
7.2 out of 10, Good, (41 reviews)
"Love the area "
United States
Jahbari
The price is CA $54
CA $155 total
includes taxes & fees
Sep 30 - Oct 1
Tempo Trek Lodgings
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
"The rooms were of good size but wished they had more soundproofing. We could easily hear noise coming from side and upstairs neighbors. The cafeteria pizza was hard to chew. Didn't try any other food from there but it looked good. Didn't like having to pay for parking. That should be included in the cost of the room. Overall we enjoyed the location and other amenities the resort had. The team members were great and knowledgeable.We would consider staying here again during there slow season."
Sally 6-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
266
Accommodation
64 Guest Houses
Lowest Price
CA $155
Highest Price
CA $522

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 $155 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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