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Featured Cottages in Kissimmee

Margarita Porch Paradise
View from room

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (1)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise
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
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
3000 Latitude Lane
Interior

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane
Orlando Home w/ Lake View, Pool & Game Room!
Private kitchen

Orlando Home w/ Lake View, Pool & Game Room!

3.0 star property
Orlando Home w/ Lake View, Pool & Game Room!
Kissimmee Vacation Home: Heated Pool, Near Disney!
Ping pong

Kissimmee Vacation Home: Heated Pool, Near Disney!

3.0 star property
Kissimmee Vacation Home: Heated Pool, Near Disney!
Luxurious Home W/private Pool, Near Disney!
Outdoor pool

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
Outdoor dining

Peaceful Home w/ Patio, 26 Mi to Disney World

3.0 star property
Peaceful Home w/ Patio, 26 Mi to Disney World
Storey Lake Resort Vacation Home
Bar (on property)

Storey Lake Resort Vacation Home

2.5 star property
Storey Lake Resort Vacation Home
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
Kissimmee Home w/ Private Pool - 8 Mi to Disney!
Outdoor pool

Kissimmee Home w/ Private Pool - 8 Mi to Disney!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a great option if you’re not staying on property. It’s a spacious townhouse with a private pool which is such a plus on those hot summer days. The rooms were nice and clean and so were the bathrooms. I was happy that they had plenty of pots and plates which made it easy for us to cook and eat before heading out to the parks. The only thing I would say is I wish they had a few more essential like Paper towels, a sponge for washing dishes and a couple extra garage bags to help make sure...
Kissimmee Home w/ Private Pool - 8 Mi to Disney!
Up to Scale With Margaritas
Property grounds

Up to Scale With Margaritas

3.0 star property
8.4 out of 10, Very good, (5)
"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
Spacious Home W/private Pool/spa & Free Waterpark!
Outdoor pool

Spacious Home W/private Pool/spa & Free Waterpark!

4.0 star property
8.0 out of 10, Very good, (2)
"The place is good, but there came a time when we felt uncomfortable, because they did not guide you well and everything you needed to know about the place. Whatever we did due to lack of orientation, they threatened us that it couldn't be done and we had to call the police. We felt intimidated during our stay. We also couldn't use the attractions, swimming pool, parks of the place because the check in of the house was different from that of the surroundings and there was a discrepancy on the...
Spacious Home W/private Pool/spa & Free Waterpark!
Beautiful, Modern Home W/private Pool! Near WDW
Outdoor pool

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.4 out of 10, Very good, (12)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW
Margaritaville Cottages Orlando
Aerial view

Margaritaville Cottages Orlando

4.0 star property
6.8 out of 10, (3)
"Great stay perfect location . Will come back everytime I’m in Orlando "
Margaritaville Cottages Orlando
Villa w/ Private Pool & Free Resort Access!
Outdoor pool

Villa w/ Private Pool & Free Resort Access!

4.5 star property
9.0 out of 10, Wonderful, (6)
"Place was absolutely beautiful! Exceeded our expectations. My family enjoyed every moment of our visit. I would definitely recommend."
Villa w/ Private Pool & Free Resort Access!
Elegant + Spacious Kissimmee Vacation Rental Home!
Interior

Elegant + Spacious Kissimmee Vacation Rental Home!

3.0 star property
8.0 out of 10, Very good, (1)
"Communication on the property was excellent. Comfortable"
Elegant + Spacious Kissimmee Vacation Rental Home!
Large Villa W/private Pool & Game Room! Waterpark
Outdoor pool

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 Lakeview Townhome w/ Private Pool!
Outdoor pool

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!
Outdoor pool

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (8)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
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

Seralago Hotel & Suites Main Gate East
2 outdoor pools, a heated pool, pool loungers

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"Foe the price you pay it s perfect!in a very good location. There could be some renovations done here and there..our door was about to break and the 2nd pool was not open. Resortfee is a little too much dor what you get!!.it used to be $9, now it s $20 per day!! Otherwise no problems. Thank you"
The price is S$87
includes taxes & fees
25 Nov - 26 Nov
Seralago Hotel & Suites Main Gate East
Ramada by Wyndham Hotel & Water Park
Water park

Ramada by Wyndham Hotel & Water Park

3.0 star property
6.8 out of 10, (1298)
"The perfect size waterpark for families with kids. Good value. "
The price is S$159
includes taxes & fees
1 Dec - 2 Dec
Ramada by Wyndham Hotel & Water Park
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1084)
"Very pretty, and spacious- but a bit far from the resort "
Margaritaville Resort Orlando Cottages by Rentyl
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.
Beautiful view of the beach with palm trees

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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 traveller favourite 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 holiday time and pick from 722 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 accommodation that are sure to impress. Book a night or two at Stunning Lakeview Townhome With Private Pool, around 8 kilometres 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 kilometres 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 holiday 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 Centre and Wizardz Magic Theatre are also visitor favourites.