Top 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

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

1. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

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

2. Upstay: Bright Family-friendly Retreat With Patio

Chatham Park

6.490.701 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A single-story house with a covered patio area, a lawn, and a clear sky.

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

Kissimmee

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

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

Kissimmee

An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

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

Kissimmee

21.482.749 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A residential house with a garage, a front door, and a driveway.

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

Reunion

13.346.658 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

7. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Indian Ridge

12.368.725 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A modern hotel with a central courtyard, palm trees, and a parking area.

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

Kissimmee

11.669.033 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Excellent

"My mom, aunt and I stayed there and got adjoining rooms. The rooms were large, comfortable and clean and the beds were great. The large sofa in the living room was also nice as was the oversized fridge. A favorite of ours was the happy hour each night (free sangria or margaritas with snacks) and the made to order omelets for breakfast (all included). The location was also excellent- minutes to great restaurants, the parks, grocery and stores. We were not there for entertainment but due to the proximity of the hotel, we went to Old Town one night (7 mins drive) and enjoyed the year round haunted house, shops, fresh pina coladas. This Embassy Suites would also be a great affordable place to stay for families going to Disney who want to conserve their cash for the parks. You cannot go wrong with this hotel. Staff were at the ready with any need. Two quick notes: while the decor was a little outdated, it is very well maintained and we did have to request housekeeping after two days but they came immediately and did a great job."

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent

"A hidden jewel in Orlando. The suites are spacious and perfect for my family of four at the time. We had no complaints, this property is kid friendly with so much to do without having to leave the area. The shopping/dining strip is a plus on top of conveniently having Target and a few other stores in walking distance. We stayed during the summer which came with free water park passes, I recommended purchasing a cabana as we did because it gets pretty hot. Overall one of the best hotel stays, I hope they continue keeping up with the property and don’t allow travelers to run it down as many of the hotels near Disney seem to experience. We are looking forward to returning for the new year. The breakfast was a plus aside from being free it’s actually good! I would recommend the breakfast area to offer favored creamer aside from that it was perfect."

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent

"The space was excellent. Excellent value for what I paid for my family to stay in a two bedroom villa. I love the size of the entire property and especially loved how peaceful environment and the privacy that our villa provided. River Island was awesome, my entire family loved every bit of it. For a three night getaway I didn’t get to do all that this property has to offer, but I was perfectly fine with what we did enjoy doing. I must say, however, that being a first time renter at this property, I foolishly agreed to their “tour of the property“ that they offer you. After you complete the tour you would receive a $200 gift card to use on the property. I knew that this was an old school timeshare proposition, but they swore that they wouldn’t give you the hard sell at the end of the tour, and I foolishly believed it. Needless to say that what was supposed to be a 90 minute tour turned into 2 1/2 hours of wasted time and they just wouldn’t take no for an answer at least for a good 20 or 30 minutes or so. Then finally they gave in and I got myself the gift card. Now, if it wasn’t that, it was a rainy day to begin with, I perhaps would’ve been more upset at the experience. But since we were basically going to be rained in for most of that day, I just rolled with it as best as I could. Otherwise, I absolutely loved my time there, and I would absolutely look into renting there again in the future. I’ll just make sure to avoid their “tour of the property“… Never again."

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
Accommodation	1190 Cottages
Lowest Price	2.069.954 ₫
Highest Price	21.482.749 ₫

Frequently asked questions

How much do cottages in Kissimmee cost?

You can expect to pay between 2.069.954 ₫ and 21.482.749 ₫ 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 0.0. 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 1190 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?

Get cosy 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 holiday here in style! Why not choose 4720shd Ultimate New 6 Bedroom Storey Lake Home? Located around 8 kms 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 kms 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 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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Our top choices for Kissimmee cottages

1. Serenity - Family & Pet Friendly, Amazing Location

2. Upstay: Bright Family-friendly Retreat With Patio

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

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

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

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

7. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

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

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

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

11. Lake Ida Beach Resort

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

Find holiday rentals that suit your style

Top Kissimmee Hotel Reviews

Embassy Suites by Hilton Orlando Lake Buena Vista South

Hilton Vacation Club Mystic Dunes Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

Embassy Suites By Hilton Orlando Sunset Walk

Quality Inn & Suites By the Parks

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Galleria Palms Hotel

Holiday Inn Resort Kissimmee by the Parks by IHG

Find out more about Kissimmee

Kissimmee Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Cottages in Kissimmee

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. Upstay: Bright Family-friendly Retreat With Patio

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

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

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

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

7. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

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

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

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

11. Lake Ida Beach Resort

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

Find holiday 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