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Check prices for these dates

Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
In one month
Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Cottages in Winter Garden

Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (1)
"Honestly the place is very clean, affordable, and is close to the theme parks! The location is safe and relaxing to just get away. Deanna is very accommodating to the needs of her guests that stay here! Thank you so much!"
$135 nightly
The price is $151
Jul 14 - Jul 15
Total includes taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Florida Guest House with Private pool & WiFi
Outdoor pool

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (38)
"We had a great time. The pool was nice to sit at. The house waa clean and lovely."
$236 nightly
The price is $261
Jul 26 - Jul 27
Total includes taxes and fees
Florida Guest House with Private pool & WiFi
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"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!"
$188 nightly
The price is $209
Jul 16 - Jul 17
Total includes taxes and fees
Downtown Cottage
Incredible Private Lakefront Cottage Retreat
Aerial view

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (26)
"One of our best stays. "
$287 nightly
The price is $317
Jul 24 - Jul 25
Total includes taxes and fees
Incredible Private Lakefront Cottage Retreat
Tiny Hidden Cottage
Fridge, microwave, stovetop, coffee/tea maker

Tiny Hidden Cottage

9.2 out of 10, Wonderful, (45)
"The house is perfect for my weekend trips to the area and I plan to stay there again if my travels permit. "
$139 nightly
The price is $153
Jul 6 - Jul 7
Total includes taxes and fees
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (22)
"Great place in beautiful quiet neighborhood. The extra touch of snacks and breakfast was a nice surprise "
$314 nightly
The price is $349
Jul 13 - Jul 14
Total includes taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (319)
"We enjoyed our stay, I loved the the view of the lake from the main bedroom ,it’s a beautiful and relaxing place."
$138 nightly
The price is $156
Jul 8 - Jul 9
Total includes taxes and fees
Orlando Lakefront Tiny House Community
Beautiful and Cozy Home at Sonoma Resort
House (6 Bedrooms) | Exterior

Beautiful and Cozy Home at Sonoma Resort

3.0 star property
$573 nightly
The price is $611
Jul 7 - Jul 8
Total includes taxes and fees
Beautiful and Cozy Home at Sonoma Resort
Disney, Universal and Legoland Getaway
A heated pool

Disney, Universal and Legoland Getaway

9.0 out of 10, Wonderful, (8)
$195 nightly
The price is $218
Aug 1 - Aug 2
Total includes taxes and fees
Disney, Universal and Legoland Getaway
Family-Friendly Cottage Near Orlando’s Top Attractions
Fridge, microwave, stovetop, coffee/tea maker

Family-Friendly Cottage Near Orlando’s Top Attractions

$182 nightly
The price is $204
Jul 9 - Jul 10
Total includes taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Iron/ironing board, travel crib, free WiFi, bed sheets

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

$172 nightly
The price is $193
Jul 7 - Jul 8
Total includes taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Dining

Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!

$210 nightly
The price is $235
Jul 11 - Jul 12
Total includes taxes and fees
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Perfect Place for a Perfect Vacation
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Perfect Place for a Perfect Vacation

3.0 star property
$171 nightly
The price is $191
Jul 6 - Jul 7
Total includes taxes and fees
Perfect Place for a Perfect Vacation
Jedi cottage 4 miles from Disney! Mins from universal!
Fridge, microwave, oven, stovetop

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
$195 nightly
The price is $218
Aug 1 - Aug 2
Total includes taxes and fees
Jedi cottage 4 miles from Disney! Mins from universal!
Beautiful, family-friendly cottage just 4 miles from Disney World
Fridge, microwave, oven, stovetop

Beautiful, family-friendly cottage just 4 miles from Disney World

9.0 out of 10, Wonderful, (8)
"Perfect for our stay in Orlando/Kissimmee. Close to everything we were attending, quiet, clean, and well supplied with the basics."
$190 nightly
The price is $213
Jul 7 - Jul 8
Total includes taxes and fees
Beautiful, family-friendly cottage just 4 miles from Disney World
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Property grounds

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

$233 nightly
The price is $260
Jul 6 - Jul 7
Total includes taxes and fees
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Cozy Tropical Cottage - 4 mi to Disney
Terrace/patio

Cozy Tropical Cottage - 4 mi to Disney

$252 nightly
The price is $282
Jul 6 - Jul 7
Total includes taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
**Charming Lakeview Cottage 4 Miles From Disney**
Smart TV, books

**Charming Lakeview Cottage 4 Miles From Disney**

$269 nightly
The price is $301
Jul 6 - Jul 7
Total includes taxes and fees
**Charming Lakeview Cottage 4 Miles From Disney**
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Fridge, microwave, oven, stovetop

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"
$201 nightly
The price is $224
Jul 13 - Jul 14
Total includes taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Hidden Lake View Cottage 5 miles from Disney!
Property grounds

Hidden Lake View Cottage 5 miles from Disney!

9.0 out of 10, Wonderful, (2)
"Awesome"
$200 nightly
The price is $224
Aug 1 - Aug 2
Total includes taxes and fees
Hidden Lake View Cottage 5 miles from Disney!
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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Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between $156 and $611 per night. These stays offer a chance to get reacquainted with nature --- at a price you can afford. 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.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable vacation on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodations that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.