Best Cottages in Kissimmee in 2026

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

Chatham Park

includes taxes & fees

24 Aug - 25 Aug

2. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

includes taxes & fees

16 Aug - 17 Aug

3. Tiny house close to Disney KISSIMMEE

Kissimmee

NOLI

includes taxes & fees

1 Sept - 2 Sept

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

Kissimmee

includes taxes & fees

14 Aug - 15 Aug

5. Perfect Place for a Perfect Vacation

Kissimmee

includes taxes & fees

26 Aug - 27 Aug

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

Kissimmee

includes taxes & fees

14 Aug - 15 Aug

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

Kissimmee

Joyce R.

includes taxes & fees

7 Sept - 8 Sept

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

Kissimmee

Jennifer b.

includes taxes & fees

12 Sept - 13 Sept

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Top Kissimmee Hotel Reviews

Kompose Boutique Resort at Theme Parks

8/10 Good

"Great place centered everywhere"

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

10/10 Excellent

"Amazing resort - have stayed in both hotel room and cottages - loved both, for convenience of having a house we prefer the cottages. British family with two kids aged 7 and 9. Only negative review to leave is that the cottages can be quite far from the main resort area which we were not aware of to be honest but no problem driving around the resort - we’d just park near the pool every day or there is a shuttle service. Absolutely love this resort the sunset walk and h20 water park is an extra bonus to have in the area! We loved popping to the water park (free of charge every day also with your booking) every morning and then going off to do whatever we were doing! Staff so friendly entertainment great’ don’t hesitate to book here!"

Legacy Vacation Resorts - Kissimmee/Orlando

10/10 Excellent

"Like it because of convenient location to all surrounding activities ,amusements & town. Also ,the general property had everything needed to enjoy without ever leaving . Very well kept and clean throughout Hotel stay. Enjoyable for family of all ages."

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews	25
Accommodation	1191 Cottages
Lowest Price	£125
Highest Price	£352

Frequently asked questions

How much do cottages in Kissimmee cost?

You can expect to pay between £125 and £352 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?

Kissimmee has multiple cottages with a total average guest review rating of 9.6. 1702vp is a fantastic option if you love nature and an easy-breezy pace. Guests staying at this 3.5-star stay can enjoy amenities such as a swimming pool and WiFi. Stunning Lakeview Townhome With Private Pool is another popular pick. This 4-star cottage comes with a swimming pool and a lazy river.

How many cottages are there in Kissimmee?

Choose from 1191 cottages in Kissimmee. No matter if you're holidaying with the kids or organising 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?

Many travellers needing a family-friendly cottage in Kissimmee pick Stunning Lakeview Townhome With Private Pool. With a 4-star rating and amenities such as a lazy river and a waterslide, you'll get a good night's rest here. Another noteworthy pick for families who crave a break close to nature is 4720shd Ultimate New 6 Bedroom Storey Lake Home. WiFi and clothes washing facilities help make this 4-star cottage a comfortable base for your Kissimmee trip. Kissimmee boasts loads of family-friendly attractions to visit when you need to keep the kids busy. 192 Flea Market and Kissimmee Golf Club promise a fun day out for visitors of all ages.

Are there any 5-star cottages in Kissimmee?

There are no 5-star cottages in Kissimmee. However, you will find some comfy 4-star accommodation that are sure to impress. Reserve your spot at Stunning Lakeview Townhome With Private Pool, around 5 mi from downtown. a swimming pool and a patio are just two of the conveniences on offer here. 4720shd Ultimate New 6 Bedroom Storey Lake Home is another stylish pick with a swimming pool and spa facilities. It's about 5 mi from the centre of Kissimmee.

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 travellers' 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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Search Kissimmee Cottages

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Kissimmee cottages

1. Upstay: Bright Family-friendly Retreat With Patio

2. Serenity - Family & Pet Friendly, Amazing Location

3. Tiny house close to Disney KISSIMMEE

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

5. Perfect Place for a Perfect Vacation

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

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

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

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

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

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

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

13. Island Life Cottage near Disney with Margaritaville Resort & Island H2O Access.

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

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

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

17. Livin in Paradise Cottage with Private Hot Tub near Disney with Margaritaville.

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

19. Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

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

Find holiday rentals that suit your style

Top Kissimmee Hotel Reviews

Kompose Boutique Resort at Theme Parks

Find out more about Kissimmee

Kissimmee Cottages information

Frequently asked questions

Explore a world of travel with Expedia