Kissimmee, FL Cottage Rentals from $151

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. Enchanted Cottage with Pool and Mini-Golf Near Disney

Kissimmee

Shane B.

$135 nightly

Sep 22 - Sep 23

Total with taxes and fees

2. Tiny house close to Disney KISSIMMEE

Kissimmee

NOLI

$148 nightly

Sep 19 - Sep 20

Total with taxes and fees

3. Upstay: Bright Family-friendly Retreat With Patio

Chatham Park

$226 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Kissimmee

$251 nightly

Sep 20 - Sep 21

Total with taxes and fees

5. Perfect Place for a Perfect Vacation

Kissimmee

$171 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Kissimmee

$186 nightly

Sep 19 - Sep 20

Total with taxes and fees

7. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

$347 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Kissimmee

$195 nightly

Sep 22 - Sep 23

Total with taxes and fees

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Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent

"The staff were very friendly. The breakfast was amazing: there was a wide variety and fresh omelets made to order! Everything was clean and towels were swapped out each day without asking. The parking lot was well lit and felt safe! It was very convenient to the parks. We did encounter 3 issues… 1st: 2/3 elevators did not work, we used the stairs because the entire hotel had to use 1 elevator. 2nd: I did not like the $25 per day parking fee: they should just increase the price per night without charging this fee. 3rd: our fridge did not work, luckily I know how to repair small appliances and I was able to fix it. Overall, it was a great hotel! We are going back this week for another 5 nights. I strongly suggest staying here!"

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews	69
Accommodation	1479 Cottages
Lowest Price	$151
Highest Price	$826

Frequently asked questions

How much do cottages in Kissimmee cost?

You can expect to pay between $151 and $826 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 9.4. 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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Things to do in Kissimmee

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Upfront pricing

Check prices for these dates

Our top choices for Kissimmee cottages

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

2. Tiny house close to Disney KISSIMMEE

3. Upstay: Bright Family-friendly Retreat With Patio

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

5. Perfect Place for a Perfect Vacation

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

7. Serenity - Family & Pet Friendly, Amazing Location

8. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

9. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

10. Family-Friendly Cottage Near Orlando’s Top Attractions

11. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

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

13. Stylish Home With Pool Hot Tub and Parking

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

15. Mvy7632 - 4BR House Near Disney

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

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

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

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

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

Find vacation rentals that suit your style

Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

Find out more about Kissimmee

Kissimmee Cottages information

Frequently asked questions

Explore a world of travel with Expedia