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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Winter Garden

Orlando Lakefront Tiny House Community
The Sunshine Lake Shake

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (327)
"We enjoyed our stay."
The price is NZ$268
includes taxes & fees
25 Aug - 26 Aug
Orlando Lakefront Tiny House Community
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is NZ$204
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom Country Cottage in Kissimmee with private parking
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!"
The price is NZ$279
includes taxes & fees
17 Aug - 18 Aug
Downtown Cottage
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (48)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
The price is NZ$244
includes taxes & fees
16 Aug - 17 Aug
Tiny Hidden Cottage
Incredible Private Lakefront Cottage Retreat
Exterior

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is NZ$545
includes taxes & fees
26 Aug - 27 Aug
Incredible Private Lakefront Cottage Retreat
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very good, (15)
"This was a cute place in a nice neighborhood "
The price is NZ$551
includes taxes & fees
11 Sept - 12 Sept
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

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

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is NZ$582
includes taxes & fees
20 Aug - 21 Aug
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

3.0 star property
The price is NZ$1,464
includes taxes & fees
17 Aug - 18 Aug
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Disney, Universal and Legoland Getaway
Exterior

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is NZ$360
includes taxes & fees
17 Aug - 18 Aug
Disney, Universal and Legoland Getaway
Jedi cottage 4 miles from Disney! Mins from universal!
Exterior

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
The price is NZ$342
includes taxes & fees
25 Aug - 26 Aug
Jedi cottage 4 miles from Disney! Mins from universal!
Charming 2-bedroom cottage in Kissimmee
Children's area

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. "
Charming 2-bedroom cottage in Kissimmee
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

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"
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
House (4 Bedrooms) | Interior

Family-friendly Home w/ Lanai ~ 6 Mi to Disney

3.0 star property
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Beautiful, family-friendly cottage just 4 miles from Disney World
Exterior

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

9.4 out of 10, Exceptional, (11)
"Perfect for our stay in Orlando/Kissimmee. Close to everything we were attending, quiet, clean, and well supplied with the basics."
The price is NZ$378
includes taxes & fees
29 Aug - 30 Aug
Beautiful, family-friendly cottage just 4 miles from Disney World
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Family-Friendly Cottage Near Orlando’s Top Attractions

The price is NZ$337
includes taxes & fees
17 Aug - 18 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
Perfect Place for a Perfect Vacation
Exterior

Perfect Place for a Perfect Vacation

3.0 star property
The price is NZ$365
includes taxes & fees
28 Aug - 29 Aug
Perfect Place for a Perfect Vacation
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

The price is NZ$254
includes taxes & fees
16 Aug - 17 Aug
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Indian Summer at Watersong Resort
Villa (Indian Summer at Watersong Resort) | Exterior

Indian Summer at Watersong Resort

2.0 star property
Indian Summer at Watersong Resort
Wellerden at Reunion Resort!by Shine Villas
House, 6 Bedrooms | Exterior

Wellerden at Reunion Resort!by Shine Villas

3.5 star property
Wellerden at Reunion Resort!by Shine Villas
Beautiful Cottage with Private Pool near Disney with Margaritaville Resort &.
Exterior

Beautiful Cottage with Private Pool near Disney with Margaritaville Resort &.

Beautiful Cottage with Private Pool near Disney with Margaritaville Resort &.
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 Winter Garden Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Everything was wonderful more than I expected!"
Tracy 4-night trip
Posted 9 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$244 and NZ$551 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.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.