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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Kissimmee cottages

House (3 Bedrooms) | Interior

1. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is ￥13,137
￥42,004 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Bright Family-friendly Retreat With Patio
Microwave, stovetop

2. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is ￥10,067
￥26,410 total
includes taxes & fees
Sep 3 - Sep 4
Tiny house close to Disney KISSIMMEE
Property grounds

3. Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
The price is ￥10,930
￥15,601 total
includes taxes & fees
Sep 3 - Sep 4
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Exterior

4. Enchanted Cottage with Pool and Mini-Golf Near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney
Kissimmee
9.4 out of 10, Exceptional, (40 reviews)
"Very nice place! Great location!"
United States
Katie W.
The price is ￥12,903
￥28,724 total
includes taxes & fees
Sep 15 - Sep 16
Enchanted Cottage with Pool and Mini-Golf Near Disney
Exterior

5. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,943
￥30,582 total
includes taxes & fees
Sep 3 - Sep 4
Perfect Place for a Perfect Vacation
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is ￥13,582
￥33,600 total
includes taxes & fees
Sep 15 - Sep 16
Newly Remodeled Tiny Home 20 minutes from Disney!~
Smart TV, books

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 ￥14,381
￥32,693 total
includes taxes & fees
Sep 22 - Sep 23
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

8. 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 ￥25,542
￥133,519 total
includes taxes & fees
Sep 3 - Sep 4
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior

9. 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 ￥15,028
￥49,672 total
includes taxes & fees
Sep 8 - Sep 9
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

10. 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 ￥14,813
￥35,156 total
includes taxes & fees
Sep 15 - Sep 16
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (4 Bedrooms) | Interior

11. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is ￥23,489
￥54,837 total
includes taxes & fees
Sep 10 - Sep 11
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (13 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is ￥14,237
￥42,398 total
includes taxes & fees
Sep 13 - Sep 14
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

13. 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 ￥26,685
￥82,421 total
includes taxes & fees
Sep 10 - Sep 11
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Exterior

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is ￥30,760
￥71,732 total
includes taxes & fees
Sep 25 - Sep 26
Mvy7664 - 3BR House Near Disney With Hot Tub
Exterior

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

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ￥30,520
￥87,253 total
includes taxes & fees
Sep 10 - Sep 11
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ￥30,520
￥87,253 total
includes taxes & fees
Sep 8 - Sep 9
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

17. Island Life Cottage near Disney w/ Margaritaville & Island H2O Access - 8026SU

Island Life Cottage near Disney w/ Margaritaville & Island H2O Access - 8026SU
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Great location for all things Disney."
United States
Chris B.
Island Life Cottage near Disney w/ Margaritaville & Island H2O Access - 8026SU
Exterior

18. Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF

Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF
Kissimmee
The price is ￥30,520
￥87,253 total
includes taxes & fees
Sep 9 - Sep 10
Livin' for the Weekend Cottage near Disney with Island H2O Access - 8021FF
Exterior

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

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
The price is ￥30,520
￥87,071 total
includes taxes & fees
Sep 10 - Sep 11
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior

20. Island Time Cottage with Hot Tub Near Disney with Margaritaville Resort &.

Island Time Cottage with Hot Tub Near Disney with Margaritaville Resort &.
Kissimmee
The price is ￥30,520
￥87,253 total
includes taxes & fees
Sep 15 - Sep 16
Island Time Cottage with Hot Tub Near Disney with Margaritaville Resort &.
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Great place to stay"
Debra 2-night trip
Posted 2 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
66
Accommodation
1479 Cottages
Lowest Price
￥15,601
Highest Price
￥133,519

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between ￥15,601 and ￥133,519 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 9.5. 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 1479 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.