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

Search Kissimmee Cottage Rentals

  • 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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Kissimmee cottages

Front of property

Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is ￥24,360
￥53,609 total
includes taxes & fees
Jul 21 - Jul 22
Ei8555 - 3BR House Near Disney
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 ￥14,162
￥59,021 total
includes taxes & fees
Jul 20 - Jul 21
Oasis Near Disney w Golf View, Family&pet Friendly
Exterior

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 ￥44,830
￥121,559 total
includes taxes & fees
Aug 6 - Aug 7
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
House (6 Bedrooms) | Interior

Family Home With Pool, BBQ & Cinema Near Disney

Family Home With Pool, BBQ & Cinema Near Disney
3.0 star property
Kissimmee
The price is ￥40,902
￥97,853 total
includes taxes & fees
Jul 23 - Jul 24
Family Home With Pool, BBQ & Cinema Near Disney
Front of property

Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is ￥33,292
￥75,002 total
includes taxes & fees
Aug 9 - Aug 10
Mvy7664 - 3BR House Near Disney With Hot Tub
Front of property

Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is ￥31,871
￥77,045 total
includes taxes & fees
Aug 6 - Aug 7
Mvy7632 - 4BR House Near Disney
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 ￥28,567
￥138,634 total
includes taxes & fees
Aug 11 - Aug 12
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (6 Bedrooms) | Interior

Garden View 6BR Escape With Pool, Hot Tub & Games

Garden View 6BR Escape With Pool, Hot Tub & Games
3.0 star property
Kissimmee
The price is ￥63,011
￥122,946 total
includes taxes & fees
Jul 21 - Jul 22
Garden View 6BR Escape With Pool, Hot Tub & Games
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 ￥14,382
￥43,788 total
includes taxes & fees
Aug 16 - Aug 17
Upstay: Bright Family-friendly Retreat With Patio
Porch

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is ￥10,740
￥12,028 total
includes taxes & fees
Jul 21 - Jul 22
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
Florence Villa
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 ￥26,634
￥65,431 total
includes taxes & fees
Jul 24 - Jul 25
Hook, Line & Leisure: Lakefront Gem w/ Porch!
House (6 Bedrooms) | Interior

Family Fun Villa w Pool, Hot Tub & Game Room

Family Fun Villa w Pool, Hot Tub & Game Room
3.0 star property
Solterra Resort
The price is ￥34,888
￥89,821 total
includes taxes & fees
Jul 19 - Jul 20
Family Fun Villa w Pool, Hot Tub & Game Room
Front of property

Th130 - 3BR House Near Disney and Universal Parks

Th130 - 3BR House Near Disney and Universal Parks
3.0 star property
Orlando
The price is ￥36,743
￥75,653 total
includes taxes & fees
Jul 26 - Jul 27
Th130 - 3BR House Near Disney and Universal Parks
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
The price is ￥26,634
￥86,956 total
includes taxes & fees
Jul 29 - Jul 30
Chic Orlando Family Getaway w/ Fenced Yard!
House (6 Bedrooms) | Interior

Upstay Spacious Home w Private Pool & Hot Tub

Upstay Spacious Home w Private Pool & Hot Tub
3.0 star property
Solana
The price is ￥21,940
￥75,320 total
includes taxes & fees
Jul 19 - Jul 20
Upstay Spacious Home w Private Pool & Hot Tub
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
The price is ￥27,439
￥59,650 total
includes taxes & fees
Aug 14 - Aug 15
Davenport Basecamp! 3BR Family Home w/ Patio
House (5 Bedrooms) | Interior

Upstay Family Home w Cinema, Pool & BBQ Clermont

Upstay Family Home w Cinema, Pool & BBQ Clermont
3.0 star property
Clermont
The price is ￥52,410
￥99,456 total
includes taxes & fees
Jul 23 - Jul 24
Upstay Family Home w Cinema, Pool & BBQ Clermont
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 ￥39,291
￥88,890 total
includes taxes & fees
Jul 20 - Jul 21
Fire Pit & Yard: Updated Winter Garden Home!
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is ￥19,163
￥55,840 total
includes taxes & fees
Aug 10 - Aug 11
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.
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

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"Todo me encantó"
Yanier 5-night trip
Posted less than an hour ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
199
Accommodation
1230 Cottages
Lowest Price
￥12,028
Highest Price
￥138,634

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between ￥12,028 and ￥138,634 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 9.1. 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 1230 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.