Search Windermere Cottage Rentals from CA $87
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Windermere Cottages

Orlando Lakefront Tiny House Community
Orlando Lakefront Tiny House Community
9.4 out of 10, Exceptional, (327)
The price is CA $89
CA $201 total
includes taxes & fees
Sep 8 - Sep 9

Lafitte's Landing Lakeview Cottage - Lakefront!
Lafitte's Landing Lakeview Cottage - Lakefront!
10.0 out of 10, Exceptional, (7)

8000 Lost Shaker Lane
8000 Lost Shaker Lane
9.6 out of 10, Exceptional, (7)

Tiny Hidden Cottage
Tiny Hidden Cottage
9.4 out of 10, Exceptional, (48)
The price is CA $98
CA $198 total
includes taxes & fees
Aug 10 - Aug 11

Family 4BR Home w/ Resort Pool Near Disney
Family 4BR Home w/ Resort Pool Near Disney

5003 Windermere Avenue
5003 Windermere Avenue
10.0 out of 10, Exceptional, (2)

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
8.4 out of 10, Very good, (15)

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Windermere Hotel Reviews

Hyatt Regency Orlando
10/10 Excellent
Find out more about Windermere
Find out more about Windermere
Windermere Cottages information
Number of reviews | 545 |
---|---|
Accommodation | 1856 Cottages |
Lowest Price | CA $87 |
Highest Price | CA $98 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Cottages in Other Destinations
More Accommodation Types in Windermere
- Vacation Homes in Windermere
- Villas in Windermere
- Condo Rentals in Windermere
- Apartments in Windermere
- Resorts in Windermere
- Aparthotels in Windermere
- Townhomes in Windermere
- Guest Houses in Windermere
- Motels in Windermere
- Condo Resorts in Windermere
- B&B in Windermere
- Residences in Windermere
- Farmstay in Windermere
- Cabin Rentals in Windermere
- Chalets in Windermere
- Houseboats in Windermere
- Riads in Windermere
- RV Parks in Windermere
- Holiday Park Resorts in Windermere
- Hostels in Windermere
- Lodges in Windermere
- Castles in Windermere
- Hotels
All Accommodation Types
Be inspired: Top Cottages destinations in 2025
- Algonquin Park Cottages
- Jasper National Park Cottages
- Tofino Cottages
- Cultus Lake Cottages
- Waterton Park Cottages
- Sunshine Coast Cottages
- Hope Cottages
- Radium Hot Springs Cottages
- Kananaskis Cottages
- Wasaga Beach Cottages
- Calgary Cottages
- Harrison Hot Springs Cottages
- Moncton Cottages
- Northern Ontario Cottages
- Kingston Cottages
- Mont-Tremblant Cottages
- Chilliwack Cottages
- Kenora Cottages
- Halifax Cottages
- Collingwood Cottages
More ways to book
Expedia's Latest Trends
Hotels
- Best Hotels in Kissimmee
- Kissimmee Hotels with a Lazy River
- Best Hotels in Clearwater
- Best Hotels in Miami Beach
- Best Hotels in Clearwater Beach
- Kissimmee Cheap Hotels
- Kissimmee Waterpark Hotels
- Hollywood Oceanfront Hotels
- Best Hotels in Lake Buena Vista
- Best Hotels in Celebration
- Best Hotels in Winter Park
- Best Hotels in Dunedin
- Kissimmee Hotels with Kitchenettes
- Best Hotels in St. Pete Beach
- Kissimmee All Inclusive Resorts and Hotels
Flights
Packages
Vacation Rentals