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

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Our top choices for Kissimmee cottages

1. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$218 nightly
The price is $247
Aug 17 - Aug 18
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$188 nightly
The price is $210
Aug 17 - Aug 18
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~

3. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$348 nightly
The price is $386
Aug 17 - Aug 18
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location

4. 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
$197 nightly
The price is $220
Aug 17 - Aug 18
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

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

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
$74 nightly
The price is $81
Aug 21 - Aug 22
Total with taxes and fees
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

6. 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
$148 nightly
The price is $165
Sep 1 - Sep 2
Total with taxes and fees
Tiny house close to Disney KISSIMMEE

7. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$175 nightly
The price is $195
Aug 30 - Aug 31
Total with taxes and fees
Perfect Place for a Perfect Vacation

8. 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.
$180 nightly
The price is $202
Sep 7 - Sep 8
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions

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.
$278 nightly
The price is $311
Sep 1 - Sep 2
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

10. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
$419 nightly
The price is $476
Aug 21 - Aug 22
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

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

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (12 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
$260 nightly
The price is $291
Aug 21 - Aug 22
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

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

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
$396 nightly
The price is $449
Aug 20 - Aug 21
Total with taxes and fees
Mvy7664 - 3BR House Near Disney With Hot Tub

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

Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.
Kissimmee
$453 nightly
The price is $507
Aug 18 - Aug 19
Total with taxes and fees
Pastel Paradise Villa near Disney With Margaritaville Resort and Island H20.

14. 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.
$484 nightly
The price is $542
Aug 26 - Aug 27
Total with taxes and fees
Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access.

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

Sunny Yellow Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
$484 nightly
The price is $542
Aug 26 - Aug 27
Total with taxes and fees
Sunny Yellow Cottage near Disney with Margaritaville Resort & Island H2O Access.

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

Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$484 nightly
The price is $542
Aug 26 - Aug 27
Total with taxes and fees
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.

17. Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.

Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.
Kissimmee
$480 nightly
The price is $538
Aug 18 - Aug 19
Total with taxes and fees
Livin' for the Weekend Cottage near Disney with Margaritaville Resort & Island.

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

Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$484 nightly
The price is $542
Aug 19 - Aug 20
Total with taxes and fees
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.

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

Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
$479 nightly
The price is $536
Aug 18 - Aug 19
Total with taxes and fees
Comfy Cottage near Disney with Margaritaville Resort & Island H2O Access -.

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

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
$239 nightly
The price is $271
Aug 17 - Aug 18
Total with taxes and fees
Pond Access & Grill! Group Escape, 19 Mi to WDW
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

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
25
Accommodation
1479 Cottages
Lowest Price
$165
Highest Price
$542

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between $165 and $542 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 9.6. 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 5 miles 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 5 miles 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.

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