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

Search Cottages in Kissimmee

  • 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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Kissimmee cottages

A residential area with houses featuring sloped roofs and solar panels.

1. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is P6,116
P17,604 total
includes taxes & fees
Nov 22 - Nov 23
Upstay: Bright Family-friendly Retreat With Patio
A row of yellow buildings with numbered doors, a sidewalk, and greenery.

2. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is P5,420
P24,630 total
includes taxes & fees
Nov 15 - Nov 16
Serenity - Family & Pet Friendly, Amazing Location
A modern hotel with a curved driveway, large windows, and palm trees.

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

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is P14,325
P30,912 total
includes taxes & fees
Nov 16 - Nov 17
Mvv7482 - 3BR House Near Disney at Magic Village
A single-story house with a brick facade, a garage, and a well-maintained lawn.

4. 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 P9,079
P30,000 total
includes taxes & fees
Nov 22 - Nov 23
Kissimmee Pool Home w/ Game Room Near Disney
A two-story house with a balcony, two garages, and a brick driveway.

5. Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is P16,164
P48,365 total
includes taxes & fees
Nov 24 - Nov 25
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

6. 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 two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is P6,585
P20,777 total
includes taxes & fees
Nov 29 - Nov 30
Family Resort Home w Pool, BBQ & Game Room
A swimming pool with a fence, lounge chairs, and a palm tree.

8. 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 P4,981
P5,578 total
includes taxes & fees
Nov 20 - Nov 21
Lake Ida Beach Resort
A two-story residential building with a garage, a small tree, and a well-maintained lawn.

9. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
Golf, Dine & Unwind Poolside! Haines City Getaway
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"Very good"
Ricardo 3-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
Accommodation
1299 Cottages
Lowest Price
P5,578
Highest Price
P48,365

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between P5,578 and P48,365 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 1299 cottages in Kissimmee. No matter if you're vacationing with the kids or organizing 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 cozy 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 traveler favorite. 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 vacation here in style! Why not choose 4720shd Ultimate New 6 Bedroom Storey Lake Home? Located around 8 kilometers 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 kilometers from the center 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 travelers' 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.