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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Kissimmee

Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Dining

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
8000 Lost Shaker Lane
Miscellaneous

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
5003 Windermere Avenue
Miscellaneous

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Pool

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Interior

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

9.8 out of 10, Exceptional, (48)
"We had a great stay! Very clean, spacious for a family of 4, easy access to Disney parks, food/shopping. Will definitely stay again! "
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Outdoor pool

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!
Townhome Splash Pool BBQ Free Water Park!
Miscellaneous

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
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! "
The price is NZ$334
includes taxes & fees
14 Aug - 15 Aug
Jedi cottage 4 miles from Disney! Mins from universal!
3148 Caribbean Soul Drive
Interior

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
3050 Pirate Way
Miscellaneous

3050 Pirate Way

3.0 star property
3050 Pirate Way
3000 Latitude Lane
Interior

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
8960 Cat Palm Road
Miscellaneous

8960 Cat Palm Road

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice place to stay. Clean, quiet, secure."
8960 Cat Palm Road
Disney, Universal and Legoland Getaway
A heated pool

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is NZ$344
includes taxes & fees
10 Aug - 11 Aug
Disney, Universal and Legoland Getaway
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Pool

Elegant Family Home w/ Pool, Game Room, Themed Bedrooms

3.0 star property
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Property grounds

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is NZ$437
includes taxes & fees
10 Aug - 11 Aug
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
8462 Secret Key Cove
Miscellaneous

8462 Secret Key Cove

3.0 star property
8.0 out of 10, Very good, (1)
8462 Secret Key Cove
Gorgeous Cottage w/Private Pool *Near Disney!*
Interior

Gorgeous Cottage w/Private Pool *Near Disney!*

9.2 out of 10, Wonderful, (5)
"Love the neighborhood and rental. Perfect location."
Gorgeous Cottage w/Private Pool *Near Disney!*
3 Mi to Disney World: Family Gem w/ Private Pool!
House (6 Bedrooms) | Front of property

3 Mi to Disney World: Family Gem w/ Private Pool!

3.0 star property
3 Mi to Disney World: Family Gem w/ Private Pool!
4718 Sleepy Hollow Drive
House (6 Bedrooms) | Property amenity

4718 Sleepy Hollow Drive

3.0 star property
2.0 out of 10, (1)
"I was highly disappointed after our stay. Our air conditioner never worked and it was inconvenient for our jam packed days to wait for someone to fix this. Really ruined our evenings."
4718 Sleepy Hollow Drive
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 Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Room can use some upgrades but other then that everything was amazing had a wonderful time "
Naomi 4-night trip
Posted 13 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between NZ$334 and NZ$437 per night for cottages in Kissimmee. No matter your budget, a fantastic stay is only a few clicks away on Expedia. 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.
How many cottages are there in Kissimmee?
Choose from 1050 cottages in Kissimmee. No matter if you're holidaying with the kids or organising a weekend break with your buddies, Expedia will help you find the right place to escape the hustle and bustle.
What is there to do in Kissimmee near my cottage?
Whatever you love to do, Kissimmee has tons of things to capture your imagination. 192 Flea Market, Osceola Square Mall and Lake Cecile are on many travellers' to-do lists. Don't leave without exploring Kissimmee Golf Club, Old Town and Silver Spurs Arena either. With Expedia's hotel deals in Kissimmee, you can discover even more neat attractions like these with the money you save.