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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Kissimmee

Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | In-room 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
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, (2)
"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!"
The price is NZ$251
includes taxes & fees
21 July - 22 July
Charming 2-bedroom Country Cottage in Kissimmee with private parking
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
Beautiful, family-friendly cottage just 4 miles from Disney World
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (10)
"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$363
includes taxes & fees
22 July - 23 July
Beautiful, family-friendly cottage just 4 miles from Disney World
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!
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

9.0 out of 10, Wonderful, (8)
The price is NZ$363
includes taxes & fees
1 Aug - 2 Aug
Disney, Universal and Legoland Getaway
Large Villa W/private Pool & Game Room! Waterpark
Miscellaneous

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (11)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark
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
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!*
Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956
Outdoor pool

Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956

3.0 star property
Luxury Villa, South Facing Pool! No Rear Neighbors. Themed Rooms, Theatre & Game Room. #8so8956
3148 Caribbean Soul Drive
Interior

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
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!
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Property grounds

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is NZ$433
includes taxes & fees
16 July - 17 July
Fully-Stocked Cozy Tropical Cottage-4 mi to 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 Kissimmee cost?
You can expect to pay between NZ$251 and NZ$433 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 1053 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.