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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Kissimmee cottages

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

1. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is AED 335
AED 1,452 total
includes taxes & fees
19 Oct - 20 Oct
Serenity - Family & Pet Friendly, Amazing Location
A residential area with houses featuring sloped roofs and solar panels.

2. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is AED 253
AED 909 total
includes taxes & fees
19 Oct - 20 Oct
Upstay: Bright Family-friendly Retreat With Patio
A single-story mobile home with a front porch and a small deck.

3. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is AED 312
AED 772 total
includes taxes & fees
19 Oct - 20 Oct
Newly Remodeled Tiny Home 20 minutes from Disney!~
A modern hotel with a curved driveway, large windows, and palm trees.

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

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is AED 781
AED 1,735 total
includes taxes & fees
27 Oct - 28 Oct
Mvv7482 - 3BR House Near Disney at Magic Village
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

5. 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 AED 535
AED 3,010 total
includes taxes & fees
2 Nov - 3 Nov
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

6. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AED 298
AED 707 total
includes taxes & fees
19 Oct - 20 Oct
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

7. 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 AED 331
AED 748 total
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story house with a brick facade, a garage, and a well-maintained lawn.

8. 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 AED 529
AED 1,748 total
includes taxes & fees
19 Oct - 20 Oct
Kissimmee Pool Home w/ Game Room Near Disney
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

9. 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 AED 340
AED 804 total
includes taxes & fees
25 Oct - 26 Oct
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

10. 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 AED 345
AED 1,138 total
includes taxes & fees
19 Oct - 20 Oct
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A restaurant with outdoor seating and a thatched roof.

11. "Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (14 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is AED 393
AED 1,053 total
includes taxes & fees
27 Oct - 28 Oct
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A two-story house with a garage, a front lawn with palm trees, and a clear blue sky.

12. Family Home With Pool, BBQ & Cinema Near Disney

Family Home With Pool, BBQ & Cinema Near Disney
3.0 star property
Kissimmee
Family Home With Pool, BBQ & Cinema Near Disney
A modern hotel with a central courtyard, palm trees, and a parking area.

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is AED 707
AED 1,649 total
includes taxes & fees
20 Oct - 21 Oct
Mvy7664 - 3BR House Near Disney With Hot Tub
A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

14. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is AED 533
AED 1,195 total
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

15. The Russell Lake House

The Russell Lake House
Winter Haven
9.8 out of 10, Exceptional, (24 reviews)
"Nice place!"
United States
Jake D.
The price is AED 248
AED 774 total
includes taxes & fees
19 Oct - 20 Oct
The Russell Lake House
A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

16. 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 AED 261
AED 292 total
includes taxes & fees
25 Oct - 26 Oct
Lake Ida Beach Resort
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AED 382
AED 1,205 total
includes taxes & fees
19 Oct - 20 Oct
Family Resort Home w Pool, BBQ & Game Room
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

18. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
The price is AED 257
AED 547 total
includes taxes & fees
19 Oct - 20 Oct
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

19. Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
St. Cloud
10.0 out of 10, Exceptional, (32 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is AED 290
AED 507 total
includes taxes & fees
16 Nov - 17 Nov
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

20. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is AED 261
AED 572 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

8/10 Good
"Resort is great. The bars closed early. Rooms were nice but basic. Shower on 5th floor had hardly any pressure. The knob for shower on off was broken. Had to report to front desk so I was not charged. We specifically booked two rooms two bites to spend a day at H20 park. I also got a cabana. Got to park and they had a sign with more than half of the park closed. There was no email or info of this given to us. We checked in for cabana. Got settled walked to cabana in the candy cane kids play pool (which we specifically went and got cabana for) and it was closed off. So I walked all the way back and they said they had no idea why the kiddie play area was closed. So spent over $1500 to stay at a resort and could not use the park. My daughter is 2 and was only able to use one slide. If you were gonna shut down whole areas and half of the park you should email people that paid for tickets/cabanas before they get there. If I would have known about the park half closed I would have canceled our trip to this resort and gone to our usual spot in Orlando but figured try something new. Oh and also it was a surprise for our friends visiting us with their 5 year old which was only able to use a couple things."
Cory 2-night trip
Posted 2 hours ago
Margaritaville Resort Orlando with H2O Waterpark

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between AED 292 and AED 3,010 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 9.7. 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 1590 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 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.