A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Kissimmee cottages

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

1. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
A residential area with houses featuring sloped roofs and solar panels.

2. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is 2.019.030 ₫
6.669.140 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Upstay: Bright Family-friendly Retreat With Patio
A modern building with a parking lot, a golf cart, and a tree.

3. Mvv7482 - 3BR House Near Disney at Magic Village

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
Mvv7482 - 3BR House Near Disney at Magic Village
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

4. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is 3.929.343 ₫
21.392.665 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A single-story house with a brick facade, a garage, and a well-maintained lawn.

5. Kissimmee Pool Home w/ Game Room Near Disney

Kissimmee Pool Home w/ Game Room Near Disney
3.0 star property
Indian Ridge
The price is 3.727.440 ₫
12.316.860 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Kissimmee Pool Home w/ Game Room Near Disney
A two-story house with a garage, a front lawn with palm trees, and a clear blue sky.

6. Family Home With Pool, BBQ & Cinema Near Disney

Family Home With Pool, BBQ & Cinema Near Disney
3.0 star property
Kissimmee
The price is 3.572.130 ₫
12.251.242 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Family Home With Pool, BBQ & Cinema Near Disney
A row of modern multi-story residential buildings with balconies, a well-maintained lawn, and a clear sky.

7. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvy7664 - 3BR House Near Disney With Hot Tub
A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

8. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
Ei8555 - 3BR House Near Disney
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

9. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
The price is 1.840.424 ₫
2.061.274 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Lake Ida Beach Resort
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

10. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is 2.692.040 ₫
8.494.422 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Family Resort Home w Pool, BBQ & Game Room
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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Top Kissimmee Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Modern and very clean and spacious"
Nachma 1-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
Accommodation
1301 Cottages
Lowest Price
2.061.274 ₫
Highest Price
21.392.665 ₫

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between 2.061.274 ₫ and 21.392.665 ₫ 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 0.0. 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 1301 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 kms 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 kms 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.