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Nov 14 - Nov 16
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Cottages in Windermere

Children's area
Charming 2-bedroom cottage in Kissimmee
Charming 2-bedroom cottage in Kissimmee
2.0 star property
10.0 out of 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
Gail E.
$200 nightly
The price is $224
Nov 10 - Nov 11
Total with taxes and fees
Charming 2-bedroom cottage in Kissimmee
Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Charming 2-bedroom Country Cottage in Kissimmee with private parking
10.0 out of 10, Exceptional, (3)
"great experience. very clean and in a good area"
United States
Aubrey V.
$120 nightly
The price is $133
Nov 13 - Nov 14
Total with taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Interior
Tiny Hidden Cottage
Tiny Hidden Cottage
9.2 out of 10, Wonderful, (55)
"The house is perfect for my weekend trips to the area and I plan to stay there again if my travels permit. "
United States
Wesley P.
$131 nightly
The price is $144
Nov 9 - Nov 10
Total with taxes and fees
Tiny Hidden Cottage
Exterior
Perfect Place for a Perfect Vacation
Perfect Place for a Perfect Vacation
3.0 star property
10.0 out of 10, Exceptional, (1)
$173 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
Perfect Place for a Perfect Vacation
Exterior
Disney, Universal and Legoland Getaway
Disney, Universal and Legoland Getaway
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
$222 nightly
The price is $248
Nov 10 - Nov 11
Total with taxes and fees
Disney, Universal and Legoland Getaway
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
$230 nightly
The price is $257
Nov 15 - Nov 16
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Microwave, stovetop
Tiny house close to Disney KISSIMMEE
Tiny house close to Disney KISSIMMEE
2.0 star property
8.0 out of 10, Very Good, (1)
"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
Christine M.
$141 nightly
The price is $157
Nov 7 - Nov 8
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Property grounds
Hidden Lake View Cottage 5 miles from Disney!
Hidden Lake View Cottage 5 miles from Disney!
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
$195 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Hidden Lake View Cottage 5 miles from Disney!
Exterior
Jedi cottage 4 miles from Disney! Mins from universal!
Jedi cottage 4 miles from Disney! Mins from universal!
9.4 out of 10, Exceptional, (24)
"Some basic home features were not working, including electrical outlets and the microwave. The home smelled like burning plastic and we tried to make several bags of popcorn with no success. The home had not been entirely clean, with stickers from someone else’s vacation hanging off a doorframe. The Yoda bedside lamp was not working…my five year old was disappointed with the place! The location was great, though would not stay here again nor reccomend this rental. "
United States
Stephanie D.
$191 nightly
The price is $214
Nov 9 - Nov 10
Total with taxes and fees
Jedi cottage 4 miles from Disney! Mins from universal!
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
$426 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Fridge, microwave, oven, stovetop
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
8.6 out of 10, Excellent, (16)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
$285 nightly
The price is $315
Nov 17 - Nov 18
Total with taxes and fees
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Interior
5180 Spectacular 5bd4ba- Private Pool&spa
5180 Spectacular 5bd4ba- Private Pool&spa
3.0 star property
$383 nightly
The price is $429
Dec 1 - Dec 2
Total with taxes and fees
5180 Spectacular 5bd4ba- Private Pool&spa
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions
Family-Friendly Cottage Near Orlando’s Top Attractions
$183 nightly
The price is $205
Nov 11 - Nov 12
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior
Incredible Private Lakefront Cottage Retreat
Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (27)
"Super cool spot I sank in the main bed in bedroom Aside from that the place was amazing"
United States
Chris W.
$332 nightly
The price is $368
Nov 23 - Nov 24
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Smart TV, DVD player
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (29)
"Easy and convenient in a nice place "
United States
cameron h.
$345 nightly
The price is $382
Nov 10 - Nov 11
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
$192 nightly
The price is $215
Nov 11 - Nov 12
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
$196 nightly
The price is $220
Nov 9 - Nov 10
Total with taxes and fees
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Property grounds
Cozy Lake Front Cottage
Cozy Lake Front Cottage
10.0 out of 10, Exceptional, (17)
"As advertised!"
United States
Peter j.
$226 nightly
The price is $248
Nov 12 - Nov 13
Total with taxes and fees
Cozy Lake Front Cottage
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney
Cozy Tropical Cottage - 4 mi to Disney
$250 nightly
The price is $280
Nov 26 - Nov 27
Total with taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
$376 nightly
The price is $423
Nov 7 - Nov 8
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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

Marriott's Grande Vista

Marriott's Grande Vista

10/10 Excellent
"This was a gorgeous property to stay at, the grounds were well kept, 3 pools to enjoy with multiple hot tubs. Told my kids I could retire and live there!"
Jennifer 3-night trip
Posted 11 hours ago
Marriott's Grande Vista

Find out more about Windermere

Windermere Cottages information

Number of reviews
180
Accommodation
1837 Cottages
Lowest Price
$133
Highest Price
$476

Frequently asked questions

How much do cottages in Windermere cost?
Rates for cottages in Windermere range between $133 and $476 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. 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 and Universal Studios Florida 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 is a great attraction to add to your to-do list.

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