Search Kissimmee Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Cottages in Kissimmee

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."
$120 nightly
The price is $134
Aug 12 - Aug 13
Total includes taxes and fees
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

9.4 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."
$190 nightly
The price is $213
Aug 6 - Aug 7
Total includes taxes and fees
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!
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!
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
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
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
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)
$183 nightly
The price is $205
Aug 9 - Aug 10
Total includes taxes and fees
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
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

$233 nightly
The price is $260
Aug 6 - Aug 7
Total includes taxes and fees
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
8462 Secret Key Cove
Stunning home with a garage, lush garden, and a palm tree.

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.
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
"Love this place. "
Kristena 1-night trip
Posted 9 hours ago
Hilton Vacation Club Mystic Dunes Orlando