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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 SAR 304
SAR 979 total
includes taxes & fees
4 Nov - 5 Nov
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 SAR 342
SAR 1,483 total
includes taxes & fees
23 Oct - 24 Oct
Serenity - Family & Pet Friendly, Amazing Location
An outdoor patio with a wooden table and chairs, a built-in grill, and a view of a residential area.

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

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
Mvv7482 - 3BR House Near Disney at Magic Village
A modern kitchen with a central island, stainless steel appliances, and a dining area with a casual seating arrangement.

4. Heated Pool & Bathtub 4BR Near Disney

Heated Pool & Bathtub 4BR Near Disney
3.0 star property
Indian Point
Heated Pool & Bathtub 4BR Near Disney
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is SAR 319
SAR 781 total
includes taxes & fees
20 Nov - 21 Nov
Newly Remodeled Tiny Home 20 minutes from Disney!~
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

6. 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 SAR 673
SAR 3,218 total
includes taxes & fees
25 Oct - 26 Oct
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

7. 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
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

8. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is SAR 304
SAR 718 total
includes taxes & fees
1 Nov - 2 Nov
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

9. 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 SAR 375
SAR 806 total
includes taxes & fees
17 Nov - 18 Nov
Family-Friendly Cottage Near Orlando’s Top Attractions
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 SAR 394
SAR 1,179 total
includes taxes & fees
22 Nov - 23 Nov
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A two-story house with a garage, a front lawn with palm trees, and a clear blue sky.

11. 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 single-story house with a brick facade, a garage, and a well-maintained lawn.

12. Kissimmee Pool Home w/ Game Room Near Disney

Kissimmee Pool Home w/ Game Room Near Disney
3.0 star property
Indian Ridge
Kissimmee Pool Home w/ Game Room Near Disney
A modern multi-story residential building with a flat roof, large windows, and a landscaped front yard.

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
Mvy7664 - 3BR House Near Disney With Hot Tub
A restaurant with outdoor seating and a thatched roof.

14. "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 SAR 746
SAR 1,493 total
includes taxes & fees
20 Nov - 21 Nov
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

15. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is SAR 544
SAR 1,221 total
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
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 SAR 264
SAR 295 total
includes taxes & fees
25 Oct - 26 Oct
Lake Ida Beach Resort
A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

17. 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 Russell Lake House
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.

18. 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 SAR 296
SAR 518 total
includes taxes & fees
18 Nov - 19 Nov
Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking
A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

19. 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 SAR 263
SAR 558 total
includes taxes & fees
22 Nov - 23 Nov
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is SAR 390
SAR 1,231 total
includes taxes & fees
25 Oct - 26 Oct
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.
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Top Kissimmee Hotel Reviews

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"I love love love marker. It’s my favorite resort. I love the staff. They were amazing. Specifically Danny and Becky were great."
Michaela 5-night trip
Posted 8 hours ago
Margaritaville Resort Orlando with H2O Waterpark

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between SAR 295 and SAR 3,218 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 1480 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.