Search Cottages in Kissimmee

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Kissimmee and around

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

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
Welcome to Margaritaville, a charming two-story residence with a front porch and lush garden.

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
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."
Charming 2-bedroom Country Cottage in Kissimmee with private parking
5003 Windermere Avenue
Relax by the pool with a meal at this outdoor dining area, featuring a table and chairs under a pendant light.

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
Enjoy dining al fresco with a view of the surrounding buildings from this outdoor patio, featuring a table, chairs, and a sofa.

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!
Overlooking a charming street lined with pastel-hued houses, this residence features a balcony with a white railing.

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
Fitness center entrance with a welcoming walkway and lush surroundings.

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
Situated among mature trees, this single-story home features a gabled roof and large windows.

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."
Beautiful, family-friendly cottage just 4 miles from Disney World
Modern Townhome W/private Pool & Free Water Park!
Residents can enjoy a central swimming pool complex surrounded by well-maintained lawns and pathways.

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
Ford's Garage features a charming garden and a single-story building with a flat roof.

3050 Pirate Way

3.0 star property
3050 Pirate Way
3000 Latitude Lane
Relax by the pool surrounded by a beautifully maintained patio with seating.

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 poolside patio with a glass table and four chairs, surrounded by a shaded area.

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
Cozy home with a gabled roof, featuring a combination of siding and brickwork, a small porch, and a well-manicured lawn.

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
Disney, Universal and Legoland Getaway
Large Villa W/private Pool & Game Room! Waterpark
Stately Mediterranean-style building with a central entrance, surrounded by lush greenery and a well-manicured lawn.

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
Relax by the pool in this serene outdoor space, featuring a sofa, chairs, and a glass table.

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!*
Enjoy the serene view of the surrounding residential area from this balcony with a seating area.

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
Fitness center entrance with covered walkway and lush greenery.

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
Relax in style on the patio with two Adirondack chairs, surrounded by a beautifully landscaped garden.

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
Townhome Splash Pool BBQ Free Water Park!
Stunning two-story building with a central entrance, surrounded by lush greenery and a beautifully manicured lawn.

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
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

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kissimmee Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"This was a quick trip with my best friend. Although I stayed here before, she had ont and was overwhelmed with the room. Spacious layout, stocked with the necessities and quiet for some much needed relaxation. The front desk was a pleasant experience and the guard house security was great!"
Patricia 2-night trip
Posted 16 hours ago
Hilton Vacation Club Mystic Dunes Orlando

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between and 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.
What are the best cottages in Kissimmee?
Pick from multiple cottages in Kissimmee with a total average guest review rating of 9.6. 1702vp is a great place to relax and recharge between adventures. This 3.5-star cottage also features a swimming pool and WiFi. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another leading pick with visitors to this area. It has a 4-star rating and amenities including a swimming pool and clothes washing facilities.
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.