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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Kissimmee cottages

House (5 Bedrooms) | Interior

5 Mi to Walt Disney World! Gem w/ Resort Perks

5 Mi to Walt Disney World! Gem w/ Resort Perks
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Property manager was amazing 👏. She responded quickly, even after hours."
United States
Lameka
The price is 3.080.961 ₫
14.093.422 ₫ total
includes taxes & fees
22 Jun - 23 Jun
5 Mi to Walt Disney World! Gem w/ Resort Perks
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is 2.949.296 ₫
7.800.757 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Upstay: Bright Family-friendly Retreat With Patio
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is 3.581.288 ₫
11.028.524 ₫ total
includes taxes & fees
6 Jun - 7 Jun
Oasis Near Disney w Golf View, Family&pet Friendly
Exterior

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 6.929.266 ₫
25.090.639 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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 3.054.628 ₫
12.417.853 ₫ total
includes taxes & fees
7 Jun - 8 Jun
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
House (3 Bedrooms) | Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is 4.213.280 ₫
12.467.312 ₫ total
includes taxes & fees
6 Jun - 7 Jun
Serenity - Family & Pet Friendly, Amazing Location
House (6 Bedrooms) | Interior

Family-friendly Villa w Pool, Hot Tub & Game Room

Family-friendly Villa w Pool, Hot Tub & Game Room
3.0 star property
Kissimmee
The price is 6.925.579 ₫
16.199.272 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Family-friendly Villa w Pool, Hot Tub & Game Room
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is 2.080.307 ₫
2.329.945 ₫ total
includes taxes & fees
6 Jun - 7 Jun
Lake Ida Beach Resort
House (3 Bedrooms) | Interior

Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is 3.344.291 ₫
10.243.010 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Hook, Line & Leisure: Lakefront Gem w/ Porch!
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

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"Clean"
Jonathan 1-night trip
Posted less than an hour ago
Palazzo Lakeside Hotel

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
200
Accommodation
1128 Cottages
Lowest Price
2.329.945 ₫
Highest Price
25.090.639 ₫

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between 2.329.945 ₫ and 25.090.639 ₫ 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 8.6. 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 1128 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.