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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Kissimmee cottages

House (3 Bedrooms) | Interior
Upstay: Bright Family-friendly Retreat With Patio

Cottage in Chatham Park

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
The price is NZ$470
includes taxes & fees
6 Jan - 7 Jan 2026
Upstay: Bright Family-friendly Retreat With Patio
House (4 Bedrooms) | Interior
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is NZ$814
includes taxes & fees
10 Jan - 11 Jan 2026
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
Charming 1-bedroom cottage in Kissimmee

Cottage in Kissimmee

Charming 1-bedroom cottage in Kissimmee
Charming 1-bedroom cottage in Kissimmee
Microwave, stovetop
Tiny house close to Disney KISSIMMEE

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
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.
The price is NZ$305
includes taxes & fees
6 Jan - 7 Jan 2026
Tiny house close to Disney KISSIMMEE
Interior
Encore Swanky

Cottage in Kissimmee

Encore Swanky
3.0 star property
The price is NZ$1,461
includes taxes & fees
29 Dec - 30 Dec
Encore Swanky
Exterior
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Cottage in Kissimmee

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
The price is NZ$2,076
includes taxes & fees
29 Dec - 30 Dec
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Dining
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is NZ$364
includes taxes & fees
5 Jan - 6 Jan 2026
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Smart TV, books
Family-Friendly Cottage Near Orlando’s Top Attractions

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
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.
The price is NZ$348
includes taxes & fees
7 Jan - 8 Jan 2026
Family-Friendly Cottage Near Orlando’s Top Attractions
Private kitchen
Cozy Tropical Cottage - 4 mi to Disney

Cottage in Kissimmee

Cozy Tropical Cottage - 4 mi to Disney
The price is NZ$492
includes taxes & fees
28 Dec - 29 Dec
Cozy Tropical Cottage - 4 mi to Disney
Living area
Cozy Lake Cottage - 4 miles to Disney

Cottage in Kissimmee

Cozy Lake Cottage - 4 miles to Disney
The price is NZ$485
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy Lake Cottage - 4 miles to Disney
House (6 Bedrooms) | Interior
Upstay: 6BR Resort Home w Pool & Basketball Court

Cottage in Kissimmee

Upstay: 6BR Resort Home w Pool & Basketball Court
3.0 star property
Upstay: 6BR Resort Home w Pool & Basketball Court
Exterior
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
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.
The price is NZ$518
includes taxes & fees
7 Jan - 8 Jan 2026
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Seas the Day Cottage near Disney with Margaritaville Resort & Island H2O Access.
Exterior
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.

Cottage in Kissimmee

Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Inviting Cottage with Private Hot Tub near Disney with Margaritaville Resort &.
Exterior
Celestial Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Cottage in Kissimmee

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

Cottage in Kissimmee

Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
2.0 star property
Dreamy Coral Cottage with Hot Tub near Disney with Margaritaville Resort &.
Exterior
The Lime Life Cottage near Disney with Margaritaville Resort and Island H20.

Cottage in Kissmmmee

The Lime Life Cottage near Disney with Margaritaville Resort and Island H20.
2.0 star property
The Lime Life Cottage near Disney with Margaritaville Resort and Island H20.
Exterior
A Parrot's Live for Me Cottage with Private Pool near Disney with.

Cottage in Kissimmee

A Parrot's Live for Me Cottage with Private Pool near Disney with.
2.0 star property
A Parrot's Live for Me Cottage with Private Pool near Disney with.
Outdoor dining
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.

Cottage in Kissimmee

Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
2.0 star property
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
Exterior
Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.

Cottage in Kissimmee

Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.
Coral Reef Cottage! near Disney with Margaritaville Resort & Island H2O Access.
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

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"Clean, greate breakfast "
Leisvi 1-night trip
Posted 2 days ago
Palazzo Lakeside Hotel

Find out more about Kissimmee

Kissimmee Cottages information

Number of reviews
2
Accommodation
1056 Cottages
Lowest Price
NZ$305
Highest Price
NZ$2,076

Frequently asked questions

How much do cottages in Kissimmee cost?
You can expect to pay between NZ$305 and NZ$2,076 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.
How many cottages are there in Kissimmee?
Choose from 1056 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.
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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