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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Kissimmee cottages

Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
2.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
$165 nightly
The price is $185
Dec 23 - Dec 24
Total with taxes and fees
Tiny house close to Disney KISSIMMEE
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

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

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
$419 nightly
The price is $472
Dec 23 - Dec 24
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
Charming 1-bedroom cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee
Kissimmee
$208 nightly
The price is $234
Dec 30 - Dec 31
Total with taxes and fees
Charming 1-bedroom cottage in Kissimmee
Property grounds
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

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
$188 nightly
The price is $211
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
House (6 Bedrooms) | Interior
Encore Swanky

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
$738 nightly
The price is $836
Dec 29 - Dec 30
Total with taxes and fees
Encore Swanky
House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$239 nightly
The price is $271
Jan 7 - Jan 8, 2026
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
Exterior
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

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
$1,072 nightly
The price is $1,217
Dec 29 - Dec 30
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

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)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1)
"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.
$180 nightly
The price is $202
Jan 7 - Jan 8, 2026
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
Terrace/patio
Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney

Cozy Tropical Cottage - 4 mi to Disney
Kissimmee
$255 nightly
The price is $285
Dec 28 - Dec 29
Total with taxes and fees
Cozy Tropical Cottage - 4 mi to Disney
Private kitchen
Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney

Cozy Lake Cottage - 4 miles to Disney
Kissimmee
$253 nightly
The price is $283
Dec 23 - Dec 24
Total with taxes and fees
Cozy Lake Cottage - 4 miles to Disney
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.8 out of 10, Exceptional, (6)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
$268 nightly
The price is $300
Jan 7 - Jan 8, 2026
Total with taxes and fees
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Kissimmee
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
2.0 star property
Kissimmee
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.

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

Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Exterior
A Parrot's Live for Me Cottage with Private Pool near Disney with.

A Parrot's Live for Me Cottage with Private Pool near Disney with.

A Parrot's Live for Me Cottage with Private Pool near Disney with.
2.0 star property
Kissimmee
A Parrot's Live for Me Cottage with Private Pool near Disney with.
House, 6 Bedrooms | Exterior
Wellerden at Reunion Resort!by Shine Villas

Wellerden at Reunion Resort!by Shine Villas

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
Reunion
Wellerden at Reunion Resort!by Shine Villas
Exterior
Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

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

Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Kissimmee
Breezy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Exterior
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Kissimmee
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Outdoor dining
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.

Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.

Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
2.0 star property
Kissimmee
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
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

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

10/10 Excellent
"The kids had a great time! I regret that I didn’t have a longer stay to enjoy more of the amenities. The staff went above and beyond!"
Londrea 1-night trip
Posted 1 day ago
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
4
Accommodation
1055 Cottages
Lowest Price
$185
Highest Price
$1,217

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between $185 and $1,217 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 9.5. 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 1055 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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