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 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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 CA $115
CA $363 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Bright Family-friendly Retreat With Patio
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $117
CA $292 total
includes taxes & fees
Sep 11 - Sep 12
Newly Remodeled Tiny Home 20 minutes from Disney!~
Exterior

3. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $112
CA $267 total
includes taxes & fees
Sep 11 - Sep 12
Perfect Place for a Perfect Vacation
Private kitchen

4. 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 CA $93
CA $235 total
includes taxes & fees
Sep 14 - Sep 15
Tiny house close to Disney KISSIMMEE
Exterior

5. 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, (42 reviews)
"This place was the perfect little hideaway during our trip to the parks. Would most definitely stay again."
United States
Shane B.
The price is CA $111
CA $248 total
includes taxes & fees
Sep 17 - Sep 18
Enchanted Cottage with Pool and Mini-Golf Near Disney
Exterior

6. 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 CA $130
CA $428 total
includes taxes & fees
Sep 14 - Sep 15
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Dining

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
The price is CA $128
CA $305 total
includes taxes & fees
Sep 22 - Sep 23
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (4 Bedrooms) | Interior

8. 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 CA $203
CA $473 total
includes taxes & fees
Sep 14 - Sep 15
Pond Access & Grill! Group Escape, 19 Mi to WDW
Living area

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 CA $124
CA $281 total
includes taxes & fees
Sep 21 - Sep 22
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

10. 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 CA $221
CA $1,153 total
includes taxes & fees
Sep 20 - Sep 21
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (6 Bedrooms) | Interior

11. Bella Vida House With Pool and Games - Near Disney!

Bella Vida House With Pool and Games - Near Disney!
3.0 star property
Bellavida
The price is CA $183
CA $645 total
includes taxes & fees
Sep 13 - Sep 14
Bella Vida House With Pool and Games - Near Disney!
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 CA $123
CA $366 total
includes taxes & fees
Sep 13 - Sep 14
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Exterior

13. 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
House (4 Bedrooms) | Interior

14. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is CA $198
CA $656 total
includes taxes & fees
Sep 14 - Sep 15
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Porch

15. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (195 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is CA $93
CA $104 total
includes taxes & fees
Sep 14 - Sep 15
Lake Ida Beach Resort
Exterior

16. Garden Retreat in St. Cloud with WiFi, AC.

Garden Retreat in St. Cloud with WiFi, AC.
St. Cloud
10.0 out of 10, Exceptional, (32 reviews)
"Great cute and clean place."
United States
Victoria T.
The price is CA $131
CA $216 total
includes taxes & fees
Sep 13 - Sep 14
Garden Retreat in St. Cloud with WiFi, AC.
Exterior detail

17. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $88
CA $243 total
includes taxes & fees
Sep 13 - Sep 14
Downtown Cottage
House (4 Bedrooms) | Interior

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $157
CA $468 total
includes taxes & fees
Oct 1 - Oct 2
Family Resort Home w Pool, BBQ & Game Room
Exterior

19. 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 CA $98
CA $215 total
includes taxes & fees
Sep 11 - Sep 12
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (4 Bedrooms) | Floor plan

20. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is CA $124
CA $450 total
includes taxes & fees
Oct 5 - Oct 6
Family 4BR Home w/ Resort Pool Near 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.
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Top Kissimmee Hotel Reviews

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Everything was amazing! So amazing we booked another stay!!!!"
Deja 1-night trip
Posted less than an hour ago
Vacation Village Orlando, Celebration

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
294
Accommodation
1480 Cottages
Lowest Price
CA $104
Highest Price
CA $1,153

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between CA $104 and CA $1,153 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 9.2. 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 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 traveller favourite. 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 kilometres 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 kilometres from the centre 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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