Title: Windermere Cottages from CA $195 | Expedia.ca [Hotels in Windermere](https://expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels)[Vacation Rentals in Windermere](https://expedia.ca/Windermere-Vacation-Rentals.d6085091.Travel-Guide-VacationRentals)[Flights to Windermere](https://expedia.ca/Cheap-Flights-To-Windermere.d6085091.Travel-Guide-Flights)[Things to do in Windermere](https://expedia.ca/Things-To-Do-In-Windermere.d6085091.Travel-Guide-Activities)[Windermere Car Rentals](https://expedia.ca/Car-Rentals-In-Windermere.d6085091.Car-Rental-Guide)[Windermere Vacation Packages](https://expedia.ca/Windermere.d6085091.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/533000/533443-tibet-butler-preserve.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Windermere Cottage Rentals from CA $195 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windermere Cottages ![Exterior](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/f102b0ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/e45cbe4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/c80dac62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/27023299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom Country Cottage in Kissimmee with private parking Kissimmee 10/10 Exceptional (3) "great experience. very clean and in a good area" CA $147 CA $195 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Country-Cottage-In-Kissimmee-With-AC.h117149949.Hotel-Information) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/21a7018d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/ae67c445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, bidet, towels](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/df24efac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/cfe5ad56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Cottage Colonialtown North 8.4/10 Very good (6) "Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!" CA $88 CA $245 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Downtown-Cottage.h110815947.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/95ab5ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/8480e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/cedf5946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/bbd3365c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Hidden Cottage Longwood 9.2/10 Wonderful (53) "We had such a great time staying here. A cute little spot made a great quick stay for us." CA $111 CA $215 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Orlando-Hotels-Tiny-Cottage.h88627180.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/w2408h1170x62y0-7347922c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/474cbed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/5d9eae4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/54993cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Incredible Private Lakefront Cottage Retreat Altamonte Springs 10/10 Exceptional (27) "One of our best stays. " CA $175 CA $479 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Orlando-Hotels-Private-Lakefront-Cottage.h37148655.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/b73e0a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/945e14a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/906240fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/0eda7c58_edited_1bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee Kissimmee 10/10 Exceptional (2) "We stayed and visited universal snd drove to Jacksonville it was a cute cottage" CA $120 CA $331 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Beautiful-Cottage-Your-Home-Away-From-Home-4-Miles-From-Disney.h107619849.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/430ce2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/2682d620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/bddeca81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/ecbaa983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema Kissimmee CA $243 CA $1,192 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-4193-Paragraph-Drive.h113092482.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/8f02e263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/8224d871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/bf0d1cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/21005d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Lake View Cottage 5 miles from Disney! Kissimmee 9.0/10 Wonderful (2) "Awesome" CA $112 CA $306 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Hidden-Lake-View-Cottage-5-Miles-From-Disney.h72359158.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/7fe0c743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/w750h561x0y0-8dd68549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/0928c447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/9b26402a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney, Universal and Legoland Getaway Kissimmee 9.2/10 Wonderful (9) "I love the place ! It was beautiful! Enough room for everyone " CA $105 CA $302 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Vrbo-Property.h45682757.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109610000/109609300/109609293/b23accde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109610000/109609300/109609293/4c3f9ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109610000/109609300/109609293/c443f6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109610000/109609300/109609293/c3c3c844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches, Altamonte Springs 8.6/10 Excellent (16) "The AC gave us trouble a few times. Host was great! Had some waters and granola bars there for us which was a nice touch. " CA $192 CA $436 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Orlando-Hotels-Hidden-Garden-Cottage-Sleeps-6.h109609293.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/f8838170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/w750h561x0y0-166794de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/9d834719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63750000/63741700/63741626/b3ea201a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jedi cottage 4 miles from Disney! Mins from universal! Kissimmee 9.4/10 Exceptional (23) "We loved staying here! " CA $105 CA $302 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Jedi-Cottage-4-Miles-From-Disney-Mins-From-Universal.h63741626.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/638cd47a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/fe821527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/994d0a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/676c3433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect Place for a Perfect Vacation Kissimmee 10/10 Exceptional (1) CA $131 CA $294 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Perfect-Place-For-A-Perfect-Vacation.h70286316.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/5a590007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/3e4c71af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/fde69571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/139634ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom cottage in Kissimmee Kissimmee 10/10 Exceptional (1) "Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. " CA $145 CA $357 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Cottage-In-Kissimmee.h107721689.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/71673f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/c4253579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/f8c94a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/82c0666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny house close to Disney KISSIMMEE Kissimmee CA $78 CA $220 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350020/e9645af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350020/622633e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350020/0ea5968d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119360000/119350100/119350020/a3845f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 161 - 4 bed Gem at Terraverde Resort Kissimmee CA $168 CA $475 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Orlando-Hotels-161-4-Bed-Gem-At-Terraverde-Resort.h119350020.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/cd9f46f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/f9892743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/fc7ee462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/0a16e2ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway! College Park 10/10 Exceptional (28) "Easy and convenient in a nice place " CA $252 CA $494 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Orlando-Hotels-The-Coach-House-Entire-Home-2-Bedroom3-Bath-Orlando-Getaway.h96021481.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/w1124h861x1y0-e56aebb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d9043965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/35cf1402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC Kissimmee CA $113 CA $288 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/dcad85d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/25aafbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/3ed7040c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/c31b3466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Cottage Near Orlando’s Top Attractions Kissimmee CA $126 CA $287 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/103000000/102470000/102460200/102460198/d0e338fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/103000000/102470000/102460200/102460198/43f4b724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/103000000/102470000/102460200/102460198/cb3270d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/103000000/102470000/102460200/102460198/c52428ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-friendly Home w/ Lanai ~ 6 Mi to Disney Montego Bay CA $227 CA $607 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Home-W-Game-Room-6-Mi-To-Disney.h102460198.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/c40e14f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/717f73dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/91196b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917000/109916919/e3e411c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more! Kissimmee CA $125 CA $312 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Orlando-Hotels-Charming-Cottage-10-Mins-To-Disney.h109916919.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/7fd1f046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/8e558232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/9c50ec99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96060000/96050800/96050707/e90548cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Tropical Cottage - 4 mi to Disney Kissimmee CA $186 CA $395 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Orlando-Hotels-Cozy-Tropical-Cottage-4-Mi-To-Disney.h96050707.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26®ionId=6085091&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindermere-Cottages.d6085091-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindermere-Cottages.d6085091-aaCottages.Travel-Guide-Accommodation) ## Top Windermere Hotel Reviews ![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](//images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1_y.jpg) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center 10/10 Excellent "This is an ideal location to Disney Parks (15 minutes or less to all of them) and has enough dining options for when you’re done with the parks. We appreciated the covered parking and walkability to the Flamingo Crossing plaza. Target is in the plaza for anyone who may have forgotten anything. The hotel was clean and free breakfast was an added bonus. The staff was very hospitable. " [](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Plenty of swimming areas for kids and volleyball area. I especially loved the calming lake view from our balcony." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Home2 Suites by Hilton Orlando at Flamingo Crossings](//images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d_y.jpg) ### Home2 Suites by Hilton Orlando at Flamingo Crossings 10/10 Excellent "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![DoubleTree by Hilton Orlando Airport](//images.trvl-media.com/lodging/1000000/20000/12300/12270/5d85f82f_y.jpg) ### DoubleTree by Hilton Orlando Airport 10/10 Excellent "Very friendly staff and clean facilities. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Airport.h12270.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was nice I saw kids enjoying the lazy river on one pool and the slide had kids playing with no problem. I have 7 kids and I think they would really enjoy this resort." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Our stay was great!" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Universal's Endless Summer Resort - Dockside Inn and Suites](//images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg) ### Universal's Endless Summer Resort - Dockside Inn and Suites 10/10 Excellent "Nice place" [](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Absoluteky enjoyed my week there, can not wait to come back. Perfect for families and solo travelers :) " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Very nice property for couples or families." [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ## Find out more about Windermere ## Windermere Cottages information | Number of reviews | 165 | | --- | --- | | Accommodation | 1838 Cottages | | Lowest Price | CA $195 | | Highest Price | CA $1,192 | ## Frequently asked questions ### How much do cottages in Windermere cost? > Rates for cottages in Windermere range between CA $195 and CA $1,192 per night. Whatever your budget, you'll find an ideal place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Are there any family-friendly cottages in Windermere? > If you want to slow the pace down a notch in Windermere, you can't go past [Fresh And Remodeled In Vista Cay Townhome](https://www.expedia.ca/Orlando-Hotels-Fresh-And-Remodeled-In-Vista-Cay-Townhome-3br35ba-3vc045.h41356074.Hotel-Information). With a 3-star rating and amenities like a barbecue grill and a picnic area, you'll find it easy to settle in at this family-friendly cottage. Windermere boasts plenty of family-friendly attractions to visit when the kids are getting restless. [Walt Disney World® Resort](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) and [Universal Studios Florida](https://www.expedia.ca/Universal-Studios-Florida-Florida-Center.d6049239.Vacation-Attraction) guarantee a fun day out for young and old. ### Why book your cottage in Windermere with Expedia? > Reserving a cottage in Windermere is as simple as working out your travel dates and selecting your ideal place for outdoor recreation and relaxation. From luxurious retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all traveler styles. As for awesome deals? We've got them as well! ### How can I find cheap cottages in Windermere? > Expedia is here to help you locate cheap cottages in Windermere. To reserve your perfect stay in a couple of quick clicks, try out the filter tool to refine your search by star rating, budget and amenities. ### What is there to do in Windermere near my cottage? > After you've unpacked your things and settled in, head out and discover the fantastic things Windermere has for you to experience. [Isleworth Golf and Country Club](https://www.expedia.ca/Isleworth-Golf-And-Country-Club-Orlando.d6091123.Vacation-Attraction) is a great attraction to add to your to-do list. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Metro West](https://www.expedia.ca/3Star-Metro-West-Orlando-Hotels.s30-n553248635976007228-0.Travel-Guide-Filter-Hotels) - [Hotels near Arnold Palmer's Bay Hill Golf Club](https://www.expedia.ca/Arnold-Palmers-Bay-Hill-Golf-Club-Hotels.0-l6069329-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Bay Hill](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-All-Inclusive-Hotel.0-n553248635975849893-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Bay Hill](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-Beach-Hotel.0-n553248635975849893-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bay Hill](https://www.expedia.ca/Bay-Hill-Orlando-Hotels-Cheap-Hotels.0-n553248635975849893-0-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Riads in Pinellas Park](https://www.expedia.ca/Pinellas-Park-Riads.d9113-aaRiads.Travel-Guide-Accommodation) - [Lodges in Polk City](https://www.expedia.ca/Polk-City-Lodges.d6154853-aaLodges.Travel-Guide-Accommodation) - [Riads in Polk City](https://www.expedia.ca/Polk-City-Riads.d6154853-aaRiads.Travel-Guide-Accommodation) - [Farmstay in Southwest Orlando](https://www.expedia.ca/Southwest-Orlando-Agritourism.d553248635976470816-aaAgritourism.Travel-Guide-Accommodation) - [Guest Houses in Southwest Orlando](https://www.expedia.ca/Southwest-Orlando-Guest-Houses.d553248635976470816-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in Southwest Orlando](https://www.expedia.ca/Southwest-Orlando-Motels.d553248635976470816-aaMotels.Travel-Guide-Accommodation) - [Resorts in Southwest Orlando](https://www.expedia.ca/Southwest-Orlando-Resort-Hotels.d553248635976470816-aaResortHotels.Travel-Guide-Accommodation) - [Villas in Southwest Orlando](https://www.expedia.ca/Southwest-Orlando-Villas.d553248635976470816-aaVillas.Travel-Guide-Accommodation) - 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[Guest Houses in Winter Garden](https://www.expedia.ca/Winter-Garden-Guest-Houses.d7898-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Winter Garden](https://www.expedia.ca/Winter-Garden-Holiday-Parks.d7898-aaHolidayParks.Travel-Guide-Accommodation) - [Inns in Winter Garden](https://www.expedia.ca/Winter-Garden-Inns.d7898-aaInns.Travel-Guide-Accommodation) - [Lodges in Winter Garden](https://www.expedia.ca/Winter-Garden-Lodges.d7898-aaLodges.Travel-Guide-Accommodation) - [Motels in Winter Garden](https://www.expedia.ca/Winter-Garden-Motels.d7898-aaMotels.Travel-Guide-Accommodation) - [Rv Parks in Winter Garden](https://www.expedia.ca/Winter-Garden-RV-Parks.d7898-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Winter Garden](https://www.expedia.ca/Winter-Garden-Resort-Hotels.d7898-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Winter Garden](https://www.expedia.ca/Winter-Garden-Townhomes.d7898-aaTownhomes.Travel-Guide-Accommodation) - [Flights to Gotha](https://www.expedia.ca/Cheap-Flights-To-Gotha.d109623.Travel-Guide-Flights) - [Flights to Orlando](https://www.expedia.ca/Cheap-Flights-To-Orlando.d178294.Travel-Guide-Flights) - [Flights from Buffalo (BUF) to Orlando (MCO)](https://www.expedia.ca/lp/flights/buf/mco/buffalo-to-orlando) - [Flights from Montreal (YUL) to Orlando (MCO)](https://www.expedia.ca/lp/flights/yul/mco/montreal-to-orlando) - [Flights from Toronto (YYZ) to Orlando (MCO)](https://www.expedia.ca/lp/flights/yyz/mco/toronto-to-orlando) - [Isleworth Golf and Country Club](https://www.expedia.ca/Isleworth-Golf-And-Country-Club-Orlando.d6091123.Vacation-Attraction) - [Lake Butler](https://www.expedia.ca/Lake-Butler-Florida.d6361045.Vacation-Attraction) - [Metrowest Golf Club](https://www.expedia.ca/MetroWest-Golf-Club-Metro-West.d6151765.Vacation-Attraction) - [Orlando Vacations](https://www.expedia.ca/Orlando.d178294.Destination-Travel-Guides) - [The Wizarding World of Harry PotterTM](https://www.expedia.ca/The-Wizarding-World-Of-Harry-PotterTM-Florida-Center.d6277909.Vacation-Attraction) - [Universal Orlando Resort](https://www.expedia.ca/Universal-Orlando-Resort-Florida-Center.d6347698.Vacation-Attraction) - [Universal Studios Florida](https://www.expedia.ca/Universal-Studios-Florida-Florida-Center.d6049239.Vacation-Attraction) - [Universal’s Islands of Adventure](https://www.expedia.ca/Universals-Islands-Of-Adventure-Florida-Center.d6068693.Vacation-Attraction) - [Universal’s Volcano Bay](https://www.expedia.ca/Universals-Volcano-Bay-Florida-Center.d553248633507645899.Vacation-Attraction) - [Walt Disney World® Resort](https://www.expedia.ca/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction) - [Rental cars Orlando Intl. airport](https://www.expedia.ca/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando](https://www.expedia.ca/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Car rentals near Universal Studios Florida](https://www.expedia.ca/Car-Rentals-In-Universal-Studios-Florida.d6049239.Car-Rental-Guide) - [Things to do in Orlando](https://www.expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities) - [Book Cottages in Windermere on Expedia.com](https://www.expedia.com/Windermere-Cottages.d6085091-aaCottages.Travel-Guide-Accommodation)