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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 P4,311
P15,458 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Bright Family-friendly Retreat With Patio
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

2. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is P5,220
P24,236 total
includes taxes & fees
Sep 27 - Sep 28
Serenity - Family & Pet Friendly, Amazing Location
A single-story house with a covered patio area, a lawn, and a clear sky.

3. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is P9,184
P12,592 total
includes taxes & fees
Oct 4 - Oct 5
Pond Access & Grill! Group Escape, 19 Mi to WDW
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 P11,473
P54,065 total
includes taxes & fees
Oct 5 - Oct 6
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A resort with a central swimming pool, sun loungers, and palm trees.

5. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is P12,313
P29,864 total
includes taxes & fees
Oct 6 - Oct 7
Mvy7632 - 4BR House Near Disney
A single-story house with a brick facade, a garage, and a well-maintained lawn.

6. ~ 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 P8,996
P29,727 total
includes taxes & fees
Sep 27 - Sep 28
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
A modern hotel with a central courtyard, palm trees, and a parking area.

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is P12,026
P28,046 total
includes taxes & fees
Oct 15 - Oct 16
Mvy7664 - 3BR House Near Disney With Hot Tub
An outdoor patio area with a long table and chairs, a sofa, and a stone wall.

8. Mvv7485 - 3BR House Near Disney With Hot Tub

Mvv7485 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is P13,979
P30,320 total
includes taxes & fees
Oct 13 - Oct 14
Mvv7485 - 3BR House Near Disney With Hot Tub
A modern building with large windows and a parking lot.

9. Mvv7460 - 3BR House Near Disney w/ Hot tub

Mvv7460 - 3BR House Near Disney w/ Hot tub
3.0 star property
Kissimmee
The price is P14,213
P30,593 total
includes taxes & fees
Oct 13 - Oct 14
Mvv7460 - 3BR House Near Disney w/ Hot tub
A modern hotel with a curved driveway, large windows, and palm trees.

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

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is P14,135
P30,502 total
includes taxes & fees
Oct 2 - Oct 3
Mvv7482 - 3BR House Near Disney at Magic Village
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is P6,497
P20,502 total
includes taxes & fees
Sep 30 - Oct 1
Family Resort Home w Pool, BBQ & Game Room
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

12. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (197 reviews)
"Clean room and private area loved it"
United States
Heather
The price is P4,442
P4,975 total
includes taxes & fees
Oct 9 - Oct 10
Lake Ida Beach Resort
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
"The best"
Chad 1-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between and 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 . 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 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.