Kissimmee Cottages from CA $122

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

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

1. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

CA $555 total

includes taxes & fees

Nov 15 - Nov 16

A hotel with a central entrance, palm trees, and a sunset sky.

2. Wp302 - 2BR Condo Near Walt Disney World

Kissimmee

CA $434 total

includes taxes & fees

Dec 12 - Dec 13

A residential area with houses featuring sloped roofs and solar panels.

3. Upstay: Bright Family-friendly Retreat With Patio

Chatham Park

CA $357 total

includes taxes & fees

Nov 22 - Nov 23

A well-maintained artificial green lawn with a flagstick, surrounded by a stone pathway and a large planter with flowers.

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

Kissimmee

CA $207 total

includes taxes & fees

Dec 9 - Dec 10

A single-story mobile home with a front porch and a small deck.

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

Kissimmee

CA $289 total

includes taxes & fees

Nov 18 - Nov 19

A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

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

Kissimmee

CA $301 total

includes taxes & fees

Dec 3 - Dec 4

A single-story house with a brick facade, a garage, and a well-maintained lawn.

7. Kissimmee Pool Home w/ Game Room Near Disney

Indian Ridge

CA $679 total

includes taxes & fees

Nov 16 - Nov 17

A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

8. Perfect Place for a Perfect Vacation

Kissimmee

Michael R.

CA $263 total

includes taxes & fees

Nov 18 - Nov 19

A modern living room with a sofa, a large wall clock, and a mirror.

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

Kissimmee

Joyce R.

CA $289 total

includes taxes & fees

Nov 17 - Nov 18

A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

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

Kissimmee

Jennifer b.

CA $423 total

includes taxes & fees

Nov 18 - Nov 19

A two-story house with a balcony, two garages, and a brick driveway.

11. Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Reunion

CA $1,111 total

includes taxes & fees

Nov 23 - Nov 24

A modern hotel with a curved driveway, large windows, and palm trees.

12. Mvv7561 - 4BR House Near Disney World

Kissimmee

CA $727 total

includes taxes & fees

Dec 8 - Dec 9

A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

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

Kissimmee

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

Kissimmee

CA $689 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with outdoor seating, a shed, and a view of the surrounding landscape.

15. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

winter have

Kyle P.

CA $201 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with lounge chairs, surrounded by palm trees and a dock extending into a body of water, during sunset.

16. The Russell Lake House

Winter Haven

Jake D.

CA $276 total

includes taxes & fees

Nov 16 - Nov 17

A residential property with a red carpet leading to a door, a small garden area with green turf and potted plants, and a wooden fence.

17. Garden in the Cloud- Cottage St. Cloud with WiFi, AC, Free parking

St. Cloud

Victoria T.

CA $186 total

includes taxes & fees

Nov 16 - Nov 17

A small, single-story house with a gray roof and white siding, featuring two white plastic chairs outside.

18. Lake Ida Beach Resort

Winter Haven

Heather

CA $122 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Solana

CA $468 total

includes taxes & fees

Nov 19 - Nov 20

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Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent

"Breakfast was amazing. The food was hot and fresh. I loved the omelet bar. The public areas were well-maintained."

Legacy Vacation Resorts - Kissimmee/Orlando

8/10 Good

"I was so excited about my birthday trip until I arrived at the resort and my room wasn’t ready. I had to wait an 1 hr pass check in and the receptionist promised to take one day resort fee off. Needless to say when I checked out she never did. I had a great time on my vacation other than this incident. I usually stay at this resort every year I was so disappointed at the check in this time. Please do better people."

Palazzo Lakeside Hotel

8/10 Good

"2nd time staying here and worth the price. Looksmlikentheres been some remodeling as the mattress seemed.new however nit was 4" sort and 4" narrower than the pedestal bedframe, but the bed was really comfortable. Also seems whoever did the floor laminate was inexperienced as there were small.gaps throughout the floor. Room had sufficient outlets to.handle my needs and lighting was good. Parking was secure and access to restaurants was convenient. Pool looked God and seems the even played movies at j right poolside. I'll stay again."

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent

"I had a great experience at this hotel! The room was clean, comfortable, and well-maintained. The staff was friendly and helpful, and the location was very convenient. Everything was pleasant, and I really enjoyed my stay. I would definitely recommend this hotel and would stay here again!"

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews	107
Accommodation	1590 Cottages
Lowest Price	CA $122
Highest Price	CA $1,111

Frequently asked questions

How much do cottages in Kissimmee cost?

You can expect to pay between CA $122 and CA $1,111 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 9.7. 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 1590 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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Kissimmee cottages

1. Serenity - Family & Pet Friendly, Amazing Location

2. Wp302 - 2BR Condo Near Walt Disney World

3. Upstay: Bright Family-friendly Retreat With Patio

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

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

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