Title: Windermere Cottages from CA $196 | Expedia.ca

 

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# Search Windermere Cottage Rentals from CA $196

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## Check prices for these dates

Next weekend

[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 two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2026-01-23&endDate=2026-01-25&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)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/f3320e10.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)

![Dining](https://images.trvl-media.com/lodging/118000000/117150000/117150000/117149949/c80dac62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

9.0/10

Wonderful

(4)

"great experience. very clean and in a good area"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Aubrey V.

CA $148

CA $196 total

includes taxes & fees

Dec 2 - Dec 3

[](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)

![Exterior detail](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/cfe5ad56.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)

![Interior](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/f0b582ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in 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!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh L.

CA $76

CA $233 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Orlando-Hotels-Downtown-Cottage.h110815947.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/d041bfdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Altamonte Springs

10/10

Exceptional

(27)

"One of our best stays. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

matthew m.

CA $159

CA $459 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Orlando-Hotels-Private-Lakefront-Cottage.h37148655.Hotel-Information)

![The Sunshine Lake Shake](https://images.trvl-media.com/lodging/97000000/96070000/96064300/96064271/2b4b3867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The View](https://images.trvl-media.com/lodging/97000000/96070000/96064300/96064271/d2e65608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Bermuda | Private kitchen](https://images.trvl-media.com/lodging/97000000/96070000/96064300/96064271/6c650c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![The Bermuda | Private kitchen](https://images.trvl-media.com/lodging/97000000/96070000/96064300/96064271/f8b1e2b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Orlando

9.4/10

Exceptional

(331)

"We enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ardeeh

CA $109

CA $225 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Orlando-Hotels-Orlando-Lakefront-Tiny-House-Community.h96064271.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)

![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)

![Beach](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/0ba4a661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Longwood

9.2/10

Wonderful

(56)

"Check in process and house were both great. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marc H.

CA $111

CA $216 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Orlando-Hotels-Tiny-Cottage.h88627180.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109610000/109609300/109609293/3ff7aaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Altamonte Springs

8.6/10

Excellent

(17)

"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachael C.

CA $193

CA $438 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Orlando-Hotels-Hidden-Garden-Cottage-Sleeps-6.h109609293.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/fc7ee462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in College Park

10/10

Exceptional

(29)

"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sara R.

CA $286

CA $539 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Orlando-Hotels-The-Coach-House-Entire-Home-2-Bedroom3-Bath-Orlando-Getaway.h96021481.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)

![Interior](https://images.trvl-media.com/lodging/108000000/107730000/107721700/107721689/59e8ff36.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)

### Cottage in 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. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gail E.

CA $95

CA $290 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Cottage-In-Kissimmee.h107721689.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)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/71000000/70290000/70286400/70286316/6cc6586b_edited_e804.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)

### Cottage in Kissimmee

10/10

Exceptional

(1)

CA $114

CA $270 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Orlando-Hotels-Perfect-Place-For-A-Perfect-Vacation.h70286316.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)

![Microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/99d15874.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)

![TV](https://images.trvl-media.com/lodging/73000000/72360000/72359200/72359158/bf0d1cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

9.0/10

Wonderful

(2)

"Awesome"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bulmaro S.

CA $113

CA $313 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Orlando-Hotels-Hidden-Lake-View-Cottage-5-Miles-From-Disney.h72359158.Hotel-Information)

![Microwave, stovetop](https://images.trvl-media.com/lodging/122000000/121010000/121006800/121006717/f5f31efd.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/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/fade59e9.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)

### Cottage in Kissimmee

9.0/10

Wonderful

(2)

"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine M.

CA $99

CA $244 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Orlando-Hotels-Tiny-House-Close-To-Disney-KISSIMMEE.h121006717.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)

![Interior](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/948252d4.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)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117630000/117622300/117622247/c31b3466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

10/10

Exceptional

(1)

"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joyce R.

CA $127

CA $286 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Cottage-Near-Orlandos-Top-Attractions.h117622247.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107619900/107619849/7b1c1f66.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)

### Cottage in Kissimmee

10/10

Exceptional

(2)

"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer b.

CA $141

CA $405 total

includes taxes & fees

Nov 26 - Nov 27

[](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/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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/46000000/45690000/45682800/45682757/59e757da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

9.2/10

Wonderful

(9)

"I love the place ! It was beautiful! Enough room for everyone "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anthony M.

CA $140

CA $346 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Orlando-Hotels-Vrbo-Property.h45682757.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96070000/96065900/96065823/64c66b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96070000/96065900/96065823/a02f84ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96070000/96065900/96065823/de1ecbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/97000000/96070000/96065900/96065823/8d527c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

CA $171

CA $373 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Orlando-Hotels-Fully-Stocked-Cozy-Tropical-Cottage-4-Mi-To-Disney.h96065823.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) | 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)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/103000000/102470000/102460200/102460198/42e99858.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)

### Cottage in Montego Bay

CA $315

CA $788 total

includes taxes & fees

Nov 29 - Nov 30

[](https://www.expedia.ca/Orlando-Hotels-Family-Friendly-Home-W-Game-Room-6-Mi-To-Disney.h102460198.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)

![Pool](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/35cf1402.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)

![Dining](https://images.trvl-media.com/lodging/118000000/117850000/117841100/117841053/d04f2cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

CA $124

CA $299 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Orlando-Hotels-Mickeys-Hideaway-Cottage-4-Miles-From-Disney-In-Kissimmee-With-WiFi-And-AC.h117841053.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/5557415a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/ed6faf61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/1fe28254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/97000000/96060000/96051000/96050914/58774300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

CA $188

CA $391 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Orlando-Hotels-Cozy-Lake-Cottage-4-Miles-To-Disney.h96050914.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/82000000/81970000/81961700/81961641/f2931e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/82000000/81970000/81961700/81961641/0d354030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/82000000/81970000/81961700/81961641/075f59fa.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/82000000/81970000/81961700/81961641/817392c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

CA $233

CA $454 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Orlando-Hotels-Charming-Lakeview-Cottage-4-Miles-From-Disney.h81961641.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/b5c4778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/98e77b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/22b2677c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/108000000/107720000/107716100/107716064/ca4aab9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Kissimmee

CA $89

CA $289 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Cottage-In-Kissimmee.h107716064.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=2025-12-09&endDate=2025-12-10&regionId=6085091&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

Black Friday Sale

Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6085091)

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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

![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg)

### Rosen Inn Lake Buena Vista

10/10 Excellent

"The staff was very helpful! We enjoyed the room we stayed in!"

[](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information)

![Hilton Orlando Lake Buena Vista - Disney Springs® Area](https://images.trvl-media.com/lodging/1000000/20000/11700/11652/0a79f404_y.jpg)

### Hilton Orlando Lake Buena Vista - Disney Springs® Area

10/10 Excellent

"I gave it a nine because I did not even see the bkfst reasturant until da going home. We are bkfst out if mkt place. It was good. "

[](https://expedia.ca/Orlando-Hotels-Hilton-Orlando-Lake-Buena-Vista-Disney-Springs-Area.h11652.Hotel-Information)

![CoCo Key Hotel and Water Resort ](https://images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg)

### CoCo Key Hotel and Water Resort 

10/10 Excellent

"The room was clean and the staff were wonderful. However what made this resort excellent are the amenities offered. The pool area was ideal for celebrating my daughter’s 6th birthday. She had a blast and she so happy therefore I was ecstatic. Loved this resort and I will be back and tell others about it! Thank you 😍"

[](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) 

![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg)

### DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent

"Clean and staff very nice "

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information)

![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg)

### DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Yes"

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)

![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg)

### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Rooms was very clean and comfortable. Very quiet! The staff was polite. "

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information)

![Walt Disney World Dolphin](https://images.trvl-media.com/lodging/1000000/20000/12800/12710/a6b6c49c_y.jpg)

### Walt Disney World Dolphin

10/10 Excellent

"Yes was a excellent experience "

[](https://expedia.ca/Orlando-Hotels-Walt-Disney-World-Dolphin.h12710.Hotel-Information)

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg)

### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Everything about it was just great. Had a very fulfilling stay. Checks all the boxes at a good price! "

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information)

![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg)

### The Grove Resort & Water Park Orlando

10/10 Excellent

"Amenities were great. Room was clean, though the showers need a caddy for those not using the shampoo, conditioner, and body wash hanging on the wall. Coffee maker provided, wish coffee pods were given. "

[](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)

## Find out more about Windermere

## Windermere Cottages information

| Number of reviews | 477 |
| --- | --- |
| Accommodation | 1831 Cottages |
| Lowest Price | CA $196 |
| Highest Price | CA $788 |

## Frequently asked questions

### How much do cottages in Windermere cost?

> Rates for cottages in Windermere range between CA $196 and CA $788 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.

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-   [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)