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Featured Cottages in Kissimmee

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (10)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark

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

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

Spacious Vacation Rental w/ Yard in Kissimmee!

3.0 star property
8.0 out of 10, Very Good, (1)
"Communication on the property was excellent. Comfortable"
Spacious Vacation Rental w/ Yard in Kissimmee!

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (9)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!

Spacious Resort Home w/ Pool - 11 Mi to Disney!

3.0 star property
8.6 out of 10, Excellent, (4)
"The house was perfect for my family of 14. It was beautiful, large and very spacious. The property manager was not resposnive but the owner wss excellent.There were a couple of minor issues, but absolutely nothing that affected our stay. I'd definitely stay there again and would recommend to everyone. "
Spacious Resort Home w/ Pool - 11 Mi to Disney!

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane

Lake-view Home w/ Game Room in Orlando!

3.0 star property
Lake-view Home w/ Game Room in Orlando!

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin

Star Stay at Championsgate Resort by Shine Villas 023

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent communication. Property was immaculate. Management was very easy to deal with and made our stay very comfortable and pleasant."
Star Stay at Championsgate Resort by Shine Villas 023

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

Luxurious Home W/private Pool, Near Disney!

4.0 star property
8.0 out of 10, Very Good, (3)
"House was great, however chose to pay for the early check-in so we could use the pool. To use the heater for the pool it’s an up charge. Understand. However they charged me $25 per day for the entire stay but the pool wasn’t warm until the morning we checked out."
Luxurious Home W/private Pool, Near Disney!

Peaceful Home w/ Patio, 26 Mi to Disney World

3.0 star property
Peaceful Home w/ Patio, 26 Mi to Disney World

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (1)
"very nice house , with 4 Rooms , 1 of them in the 1st floor so very convenient to my mom . kitchen is awesome , new and good quality appliances we take the kids to the club , there is a lazy river and the sliders are fun . No additional charges . "
5003 Windermere Avenue

Enchanting House few min Away From the Parks 52

3.0 star property
Enchanting House few min Away From the Parks 52

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive

Sea Jules at Margaritaville

3.0 star property
6.0 out of 10, (2)
"Thank you. We had a great time. Highly recommended!"
Sea Jules at Margaritaville

8462 Secret Key Cove

3.0 star property
8.0 out of 10, Very Good, (1)
8462 Secret Key Cove

Up to Scale With Margaritas

3.0 star property
8.8 out of 10, Excellent, (6)
"The only issue was the upstairs airconditioner was not working in terms the rooms were hot while hallway was cold. But nice for our family. "
Up to Scale With Margaritas
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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Other property types in Kissimmee

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1165)
"Great area with a vacation feel."
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1419)
"Place was nice and cozy, and our dog felt at home ♥️"
The price is P5,548
P7,174 total
includes taxes & fees
Feb 5 - Feb 6
Vacation Village at Parkway

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1648)
"lots of room, 4 bedroom, 3 bath with 4 adults (two adult children), everyone had own bathroom which was worked out well."
The price is P7,842
P9,408 total
includes taxes & fees
Jan 23 - Jan 24
The Berkley, Orlando
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.

Frequently asked questions

How much do cottages in Kissimmee cost?
Cottages in Kissimmee range between and per night. These properties offer a chance to soak up nature’s beauty — at a price you can afford. 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?
A traveler favorite is 1702vp. Base yourself at this 3.5-star stay which comes with a swimming pool and WiFi. Stunning Lakeview Townhome With Private Pool is another popular option worth shortlisting. Spend your break at this 4-star cottage and make the most of amenities including a swimming pool and a waterslide. There are multiple cottages in Kissimmee with a total average guest review rating of 8.8.
How many cottages are there in Kissimmee?
Claim your vacation time and pick from 726 cottages in Kissimmee. Imagining a place where you can get in touch with nature? Expedia can help you find your ideal getaway in a few quick clicks.
Are there any family-friendly cottages in Kissimmee?
A trip with your group in Kissimmee is a piece of cake at Stunning Lakeview Townhome With Private Pool. With conveniences such as a waterslide and a lazy river, you’ll find all the comforts you need at this 4-star cottage. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another family-friendly property where everyone can break free from the hustle and bustle of big city life. This cottage has a 4-star rating and conveniences including WiFi and clothes washing facilities. Once you’ve checked in and unpacked, there’s no shortage of family-friendly attractions to see around Kissimmee. Fun Spot America and Kissimmee Go-Karts promise fun for all ages.
Are there any 5-star cottages in Kissimmee?
There are no 5-star cottages in Kissimmee. But you will find some comfortable 4-star accommodations that are sure to impress. Book a night or two at Stunning Lakeview Townhome With Private Pool, around 8 kilometers from the downtown area. a swimming pool and a lanai are a couple of the amenities here. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another upscale pick with a swimming pool and beauty services. It’s about 8 kilometers from central Kissimmee.
Why book your cottage in Kissimmee with Expedia?
Reserving a cottage in Kissimmee is as easy as clicking on your travel dates and choosing an ideal place for a vacation in nature. From luxurious retreats to low-cost stays and cottages that come with conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We’ve got you covered!
How can I find cheap cottages in Kissimmee?
With Expedia’s helpful filter tool, locating cheap cottages in Kissimmee couldn’t be simpler. To view properties that’ll make your bank balance smile, narrow your search by amenities, star rating and budget.
What is there to do in Kissimmee near my cottage?
There are plenty of fabulous things that’ll fill up your itinerary in Kissimmee. You won’t want to miss big attractions like Fun Spot America, Medieval Times and Capone’s Dinner Show. Skate Reflections, AMF Bowling Center and Wizardz Magic Theater are also visitor favorites.