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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
Relax in a welcoming space with comfortable seating, lush greenery, and a striking central sculpture.

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)
"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 AU$204
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom Country Cottage in Kissimmee with private parking
5003 Windermere Avenue
Relax by the resort pool surrounded by palm trees and lounge chairs, with a golf course in the background.

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
Relax by the pool surrounded by palm trees and lounge chairs.

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!
Experience the warm and inviting lobby, featuring a unique abstract sculpture, comfortable seating, and lush greenery.

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
Relax by the resort pool surrounded by palm trees and lounge chairs.

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
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and sink, offering ample counter space and a view of the outdoors.

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 AU$339
includes taxes & fees
5 Aug - 6 Aug
Beautiful, family-friendly cottage just 4 miles from Disney World
Modern Townhome W/private Pool & Free Water Park!
Relax by the main pool, children's pool, and putting green, surrounded by palm trees and lounge chairs.

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!
Relax by the resort's curving pool surrounded by lush greenery and palm trees.

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!
3148 Caribbean Soul Drive
Experience the open and airy lobby with comfortable seating, a large abstract sculpture, and lush greenery.

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
3050 Pirate Way
Relax in style amidst comfortable seating and lush greenery, surrounded by a striking abstract sculpture and natural light.

3050 Pirate Way

3.0 star property
3050 Pirate Way
3000 Latitude Lane
Experience the elegant lobby with a striking abstract sculpture, comfortable seating, and lush greenery.

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
8960 Cat Palm Road
Relax by the resort's pool surrounded by palm trees and a small waterfall.

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
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Relax by the oval-shaped pool surrounded by palm trees and lounge chairs.

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

3.0 star property
Elegant Family Home w/ Pool, Game Room, Themed Bedrooms
Disney, Universal and Legoland Getaway
Relax by the pool surrounded by lush trees and enjoy a soak in the hot tub.

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is AU$320
includes taxes & fees
9 Aug - 10 Aug
Disney, Universal and Legoland Getaway
Large Villa W/private Pool & Game Room! Waterpark
Relax by the resort's serene pool surrounded by lush greenery and palm trees.

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
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Relax in this serene outdoor space with a comfortable sofa set, coffee table, and lush greenery.

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is AU$411
includes taxes & fees
5 Aug - 6 Aug
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
8462 Secret Key Cove
Enjoy a spacious living area with a sofa and dining table for four, a well-equipped kitchen and a balcony with a view.

8462 Secret Key Cove

3.0 star property
8.0 out of 10, Very good, (1)
8462 Secret Key Cove
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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Frequently asked questions

How much do cottages in Kissimmee cost?
Prepare to pay between AU$204 and AU$411 per night for cottages in Kissimmee. Whatever your budget, an excellent stay is only a click or two away on Expedia. This price was 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?
Pack your bags and pick from 1050 cottages in Kissimmee. Thinking about a place where you can relax and stay in touch with nature? Expedia will help you find the ideal escape in a few easy clicks.
What is there to do in Kissimmee near my cottage?
Whatever you're into, Kissimmee has loads to keep you occupied. Discovery Cove, Aquatica and Disneys Typhoon Lagoon Water Park are on most visitors' itineraries. Don't miss Gatorland®, Medieval Times and Fun Spot America either. With Expedia's hotel deals in Kissimmee, you'll be able to see more terrific attractions like these with the cash you save.