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

Search Kissimmee Cottages

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$218 nightly
The price is $247
Sep 23 - Sep 24
Total with taxes and fees
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
$148 nightly
The price is $165
Sep 22 - Sep 23
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
Exterior

3. 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, (44 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
$139 nightly
The price is $155
Sep 30 - Oct 1
Total with taxes and fees
Enchanted Cottage with Pool and Mini-Golf Near Disney
House (3 Bedrooms) | Interior

4. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$347 nightly
The price is $385
Sep 22 - Sep 23
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
House (4 Bedrooms) | Interior

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

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
$178 nightly
The price is $202
Sep 22 - Sep 23
Total with taxes and fees
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

6. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
$171 nightly
The price is $191
Sep 22 - Sep 23
Total with taxes and fees
Perfect Place for a Perfect Vacation
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$186 nightly
The price is $208
Sep 22 - Sep 23
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
Dining

8. 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
$195 nightly
The price is $218
Sep 22 - Sep 23
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
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.
$274 nightly
The price is $307
Sep 22 - Sep 23
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Smart TV, books

10. 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.
$181 nightly
The price is $203
Sep 22 - Sep 23
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

11. 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
$753 nightly
The price is $855
Oct 5 - Oct 6
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (5 Bedrooms) | Interior

12. Upstay Luxury Home With Pool, Hot Tub, Games Room

Upstay Luxury Home With Pool, Hot Tub, Games Room
3.0 star property
Reunion
$415 nightly
The price is $471
Sep 24 - Sep 25
Total with taxes and fees
Upstay Luxury Home With Pool, Hot Tub, Games Room
Exterior

13. "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.
$236 nightly
The price is $264
Sep 23 - Sep 24
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

14. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
$420 nightly
The price is $476
Oct 6 - Oct 7
Total with taxes and fees
Mvy7632 - 4BR House Near Disney
House (4 Bedrooms) | Interior

15. ~ 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
Sep 22 - Sep 23
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

16. 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
Oct 15 - Oct 16
Total with taxes and fees
Mvy7664 - 3BR House Near Disney With Hot Tub
Exterior

17. Mvv7460 - 3BR House Near Disney w/ Hot tub

Mvv7460 - 3BR House Near Disney w/ Hot tub
3.0 star property
Kissimmee
$426 nightly
The price is $482
Oct 13 - Oct 14
Total with taxes and fees
Mvv7460 - 3BR House Near Disney w/ Hot tub
Exterior

18. Mvv7485 - 3BR House Near Disney With Hot Tub

Mvv7485 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
$428 nightly
The price is $485
Oct 13 - Oct 14
Total with taxes and fees
Mvv7485 - 3BR House Near Disney With Hot Tub
Exterior

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

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
$465 nightly
The price is $526
Oct 11 - Oct 12
Total with taxes and fees
Mvv7482 - 3BR House Near Disney at Magic Village
Porch

20. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (196 reviews)
"Clean room and private area loved it"
United States
Heather
$79 nightly
The price is $88
Sep 23 - Sep 24
Total with taxes and fees
Lake Ida Beach 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

Seasons Florida Resort

Seasons Florida Resort

10/10 Excellent
"Love this place! Beds were clean and comfortable! Pool was so nice! Price was right!! Will stay again!"
Hollis 1-night trip
Posted less than an hour ago
Seasons Florida Resort

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
265
Accommodation
1479 Cottages
Lowest Price
$88
Highest Price
$855

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between $88 and $855 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 9.1. 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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