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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kissimmee cottages

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ¥13,409
¥61,519 total
includes taxes & fees
Apr 24 - Apr 25
Serenity - Family & Pet Friendly, Amazing Location

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ¥13,484
¥42,133 total
includes taxes & fees
Apr 20 - Apr 21
Upstay: Bright Family-friendly Retreat With Patio

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (6 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is ¥11,138
¥27,564 total
includes taxes & fees
May 12 - May 13
Tiny house close to Disney KISSIMMEE

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (8 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is ¥15,563
¥44,031 total
includes taxes & fees
Apr 22 - Apr 23
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Spacious Kissimmee Villa - 3 Mi to Disney World!

Spacious Kissimmee Villa - 3 Mi to Disney World!
3.0 star property
Windsor Hills
The price is ¥28,005
¥65,475 total
includes taxes & fees
Apr 19 - Apr 20
Spacious Kissimmee Villa - 3 Mi to Disney World!

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ¥12,850
¥30,521 total
includes taxes & fees
Apr 22 - Apr 23
Perfect Place for a Perfect Vacation

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is ¥12,810
¥46,446 total
includes taxes & fees
Apr 22 - Apr 23
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is ¥14,706
¥34,268 total
includes taxes & fees
Apr 26 - Apr 27
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is ¥14,278
¥32,141 total
includes taxes & fees
May 6 - May 7
Family-Friendly Cottage Near Orlando’s Top Attractions

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.
Kissimmee
The price is ¥38,550
¥89,469 total
includes taxes & fees
May 4 - May 5
Sunny Cottage near Disney with Margaritaville Resort & Island H20 Waterpark.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
The price is ¥38,666
¥89,739 total
includes taxes & fees
May 4 - May 5
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Upstay: Pet-friendly Family Home w Pool & Sundeck

Upstay: Pet-friendly Family Home w Pool & Sundeck
3.0 star property
Kissimmee
The price is ¥21,099
¥57,978 total
includes taxes & fees
Apr 30 - May 1
Upstay: Pet-friendly Family Home w Pool & Sundeck

Luxurious Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Luxurious Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ¥47,592
¥105,783 total
includes taxes & fees
Apr 20 - Apr 21
Luxurious Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Kissimmee
The price is ¥27,210
¥70,690 total
includes taxes & fees
May 5 - May 6
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

~ 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 ¥18,402
¥74,810 total
includes taxes & fees
Apr 20 - Apr 21
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ¥31,028
¥75,500 total
includes taxes & fees
May 4 - May 5
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ¥30,935
¥75,273 total
includes taxes & fees
May 4 - May 5
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ¥31,569
¥75,971 total
includes taxes & fees
May 17 - May 18
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access.

Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Great location for all things Disney."
United States
Chris B.
The price is ¥30,935
¥75,273 total
includes taxes & fees
May 4 - May 5
Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access.

Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.

Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
Kissimmee
8.0 out of 10, Very Good, (1 review)
"We’ve stayed at Margaritaville at least 4-5 times in different houses and we always have a great time. This house had a great location, as it was close to the gym and pool area. Negatives: on the listing it says there is a king bed, definitely no king bed. The first night was cold and none of the beds had anything other than sheets and when we called and requested additional blankets, we were told it was going to be $10 each blanket! The room did not come with sheets for the pull out couch so...
United States
Chad A.
The price is ¥31,028
¥75,500 total
includes taxes & fees
May 4 - May 5
Breezy Green Cottage with Private Hot Tub near Disney with Margaritaville.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kissimmee Hotel Reviews

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
19
Accommodation
1390 Cottages
Lowest Price
¥27,564
Highest Price
¥105,783

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between ¥27,564 and ¥105,783 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 9.3. 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 1390 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.