Search Cottages in Kissimmee

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Featured Cottages in Kissimmee and around

Children’s area
Charming 2-bedroom cottage in Kissimmee

Charming 2-bedroom cottage in Kissimmee

2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
United States
Gail E.
Charming 2-bedroom cottage in Kissimmee
Property grounds
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Kissimmee
The price is €198
includes taxes & fees
8 Dec - 9 Dec
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior
Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation

3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
The price is €169
includes taxes & fees
9 Nov - 10 Nov
Perfect Place for a Perfect Vacation
House (4 Bedrooms) | Interior
Terra Verde Swanky

Terra Verde Swanky

3.0 star property
Kissimmee
Terra Verde Swanky
House (4 Bedrooms) | Interior
Family-friendly Home w/ Lanai ~ 6 Mi to Disney

Family-friendly Home w/ Lanai ~ 6 Mi to Disney

3.0 star property
Montego Bay
The price is €390
includes taxes & fees
10 Nov - 11 Nov
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Kissimmee
The price is €181
includes taxes & fees
11 Nov - 12 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
Property grounds
Hidden Lake View Cottage 5 miles from Disney!

Hidden Lake View Cottage 5 miles from Disney!

Kissimmee
9.0 out of 10, Wonderful, (2)
"Awesome"
United States
Bulmaro S.
The price is €193
includes taxes & fees
3 Dec - 4 Dec
Hidden Lake View Cottage 5 miles from Disney!
Exterior
Jedi cottage 4 miles from Disney! Mins from universal!

Jedi cottage 4 miles from Disney! Mins from universal!

Kissimmee
9.4 out of 10, Exceptional, (24)
"Some basic home features were not working, including electrical outlets and the microwave. The home smelled like burning plastic and we tried to make several bags of popcorn with no success. The home had not been entirely clean, with stickers from someone else’s vacation hanging off a doorframe. The Yoda bedside lamp was not working…my five year old was disappointed with the place! The location was great, though would not stay here again nor reccomend this rental. "
United States
Stephanie D.
Jedi cottage 4 miles from Disney! Mins from universal!
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

2.0 star property
Kissimmee
8.0 out of 10, Very good, (1)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is €140
includes taxes & fees
3 Dec - 4 Dec
Tiny house close to Disney KISSIMMEE
Exterior
Disney, Universal and Legoland Getaway

Disney, Universal and Legoland Getaway

Kissimmee
9.2 out of 10, Wonderful, (9)
"I love the place ! It was beautiful! Enough room for everyone "
United States
Anthony M.
The price is €212
includes taxes & fees
6 Dec - 7 Dec
Disney, Universal and Legoland Getaway
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney

Kissimmee
The price is €248
includes taxes & fees
26 Nov - 27 Nov
Cozy Tropical Cottage - 4 mi to Disney
Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking

Charming 2-bedroom Country Cottage in Kissimmee with private parking

Kissimmee
10.0 out of 10, Exceptional, (3)
"great experience. very clean and in a good area"
United States
Aubrey V.
The price is €124
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Kissimmee
10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is €230
includes taxes & fees
15 Nov - 16 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior
Charming 1-bedroom cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee

Kissimmee
The price is €188
includes taxes & fees
1 Dec - 2 Dec
Charming 1-bedroom cottage in Kissimmee
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

3.0 star property
Indian Ridge
The price is €366
includes taxes & fees
9 Nov - 10 Nov
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Property grounds
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

Kissimmee
The price is €247
includes taxes & fees
9 Dec - 10 Dec
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds
Lafitte's Landing Lakeview Cottage - Lakefront!

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (12)
"We really enjoyed our stay, the home was so clean and comfortable.. "
United States
Geraldine
The price is €443
includes taxes & fees
23 Nov - 24 Nov
Lafitte's Landing Lakeview Cottage - Lakefront!
Interior
Solterra Swanky

Solterra Swanky

3.0 star property
Solterra Resort
The price is €371
includes taxes & fees
1 Dec - 2 Dec
Solterra Swanky
Exterior
Cozy new cottage in fantastic St. Cloud with WiFi, AC

Cozy new cottage in fantastic St. Cloud with WiFi, AC

St. Cloud
10.0 out of 10, Exceptional, (19)
"The room is super comfortable and clean. Nina and her husband are super friendly and are always in touch in case you need anything. I will definitely book with them again."
United States
Edgar
The price is €123
includes taxes & fees
9 Dec - 10 Dec
Cozy new cottage in fantastic St. Cloud with WiFi, AC
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property
Winter Garden
The price is €411
includes taxes & fees
8 Dec - 9 Dec
Fire Pit & Yard: Updated Winter Garden Home!
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.
View all properties
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

Ramada by Wyndham Hotel & Water Park

Ramada by Wyndham Hotel & Water Park

10/10 Excellent
"Good "
Joan 4-night trip
Posted 3 days ago
Ramada by Wyndham Hotel & Water Park

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
67
Accommodation
1055 Cottages
Lowest Price
€123
Highest Price
€443

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between €123 and €443 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 1055 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.
Are there any family-friendly cottages in Kissimmee?
Get cosy at 4720shd Ultimate New 6 Bedroom Storey Lake Home, a 4-star cottage not far from town. Amenities here include WiFi and clothes washing facilities. Another family-friendly pick where you can swap the concrete jungle for wide open spaces is Stunning Lakeview Townhome With Private Pool. A playground and a lazy river help make this 4-star cottage a traveller favourite. Once you've checked in and dropped off your luggage, there are lots of family-friendly attractions to see in and around Kissimmee. Discovery Cove and Aquatica guarantee fun for young and old.
Are there any 5-star cottages in Kissimmee?
Kissimmee does not have any 5-star cottages — but you and your crew can still holiday here in style! Why not choose 4720shd Ultimate New 6 Bedroom Storey Lake Home? Located around 8 kilometres from the downtown area, this 4-star retreat features beauty services and a swimming pool. Stunning Lakeview Townhome With Private Pool is another excellent 4-star choice just 8 kilometres from the centre of Kissimmee. It provides a relaxed vibe close to nature on top of amenities like a swimming pool and a lanai.
Why book your cottage in Kissimmee with Expedia?
Expedia has some great cottages in Kissimmee, so start planning for a memorable stay on nature's doorstep. If you have a certain budget, select how much you're willing to spend and the star rating of your property. Or, make your way to the filters to search for cottages with a pool or a kitchen. We'll help you find a suitable place whatever your getaway looks like.
How can I find cheap cottages in Kissimmee?
The easiest way to compare cheap cottages in Kissimmee is with Expedia's user-friendly filter tool. Narrow your search by amenities, budget and star rating to grab excellent rates in just a few clicks.
What is there to do in Kissimmee near my cottage?
Whatever you love to do, Kissimmee has tons of things to capture your imagination. 192 Flea Market, Osceola Square Mall and Lake Cecile are on many travellers' to-do lists. Don't leave without exploring Kissimmee Golf Club, Old Town and Silver Spurs Arena either. With Expedia's hotel deals in Kissimmee, you can discover even more neat attractions like these with the money you save.

Explore a world of travel with Expedia