A lakeside community with houses and boats.

Search Guest Houses in Windermere from CA $139

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Windermere guest houses

Smart TV

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 $105
CA $243 total
includes taxes & fees
Aug 11 - Aug 12
Downtown Lake Eola Historic House 1 OR 2 BED
Interior

2. Quiet Oasis in Lovely Neighborhood

Quiet Oasis in Lovely Neighborhood
Southern Oaks
9.8 out of 10, Exceptional, (194 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 $113
CA $266 total
includes taxes & fees
Aug 20 - Aug 21
Quiet Oasis in Lovely Neighborhood
TV

3. Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
The price is CA $209
CA $399 total
includes taxes & fees
Aug 31 - Sep 1
Speakeasy Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Outdoor pool, a heated pool

4. Historic lakefront guesthouse

Historic lakefront guesthouse
Orlando
10.0 out of 10, Exceptional, (13 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 $142
CA $442 total
includes taxes & fees
Sep 8 - Sep 9
Historic lakefront guesthouse
Outdoor pool, a heated pool

5. 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 $183
CA $462 total
includes taxes & fees
Aug 11 - Aug 12
Mills Cottage by the Little Lake
Hallway

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 $58
CA $161 total
includes taxes & fees
Aug 26 - Aug 27
Enchanted Fantasy
Interior

7. Mermaid Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House

Mermaid Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Oakland
The price is CA $209
CA $399 total
includes taxes & fees
Aug 31 - Sep 1
Mermaid Room in Central Florida's Historic Gem & wedding venue- The Oakland Manor House
Dining

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

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Buena Ventura Lakes
The price is CA $113
CA $295 total
includes taxes & fees
Aug 11 - Aug 12
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Outdoor pool

9. Tempo Trek Lodgings

Tempo Trek Lodgings
3.0 star property
Solterra Resort
7.2 out of 10, Good, (39 reviews)
"Love the area "
United States
Jahbari
The price is CA $41
CA $139 total
includes taxes & fees
Aug 16 - Aug 17
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windermere Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"We waited for a room and they for got about us you hours"
Jason 7-night trip
Posted 2 hours ago
The Grove Resort & Water Park Orlando

Find out more about Windermere

Windermere Guest Houses information

Number of reviews
312
Accommodation
64 Guest Houses
Lowest Price
CA $139
Highest Price
CA $462

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 $139 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.

Explore a world of travel with Expedia