Search Kissimmee Cottage Accommodations

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Cottages in Kissimmee

Our top choices for Kissimmee cottages

Jedi cottage 4 miles from Disney! Mins from universal!
Fridge, microwave, oven, stovetop

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
The price is AU$338
includes taxes & fees
3 Sept - 4 Sept
Jedi cottage 4 miles from Disney! Mins from universal!
Disney, Universal and Legoland Getaway
A heated pool

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is AU$338
includes taxes & fees
5 Sept - 6 Sept
Disney, Universal and Legoland Getaway
Hidden Lake View Cottage 5 miles from Disney!
Property grounds

Hidden Lake View Cottage 5 miles from Disney!

9.0 out of 10, Wonderful, (2)
"Awesome"
The price is AU$348
includes taxes & fees
5 Sept - 6 Sept
Hidden Lake View Cottage 5 miles from Disney!
Pool & Lazy River: Windsor House 9 Mi to Disney!
House (6 Bedrooms) | Interior

Pool & Lazy River: Windsor House 9 Mi to Disney!

3.0 star property
The price is AU$841
includes taxes & fees
25 Aug - 26 Aug
Pool & Lazy River: Windsor House 9 Mi to Disney!
Charming 2-bedroom cottage in Kissimmee
Children's area

Charming 2-bedroom cottage in Kissimmee

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
The price is AU$377
includes taxes & fees
7 Sept - 8 Sept
Charming 2-bedroom cottage in Kissimmee
Perfect Place for a Perfect Vacation
Outdoor dining

Perfect Place for a Perfect Vacation

3.0 star property
The price is AU$336
includes taxes & fees
5 Sept - 6 Sept
Perfect Place for a Perfect Vacation
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is AU$218
includes taxes & fees
24 Sept - 25 Sept
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Property grounds

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

The price is AU$273
includes taxes & fees
25 Aug - 26 Aug
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
**Charming Lakeview Cottage 4 Miles From Disney**
Smart TV, books

**Charming Lakeview Cottage 4 Miles From Disney**

The price is AU$470
includes taxes & fees
25 Aug - 26 Aug
**Charming Lakeview Cottage 4 Miles From Disney**
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (2)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
The price is AU$363
includes taxes & fees
24 Sept - 25 Sept
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Beautiful, family-friendly cottage just 4 miles from Disney World
Fridge, microwave, oven, stovetop

Beautiful, family-friendly cottage just 4 miles from Disney World

9.4 out of 10, Exceptional, (11)
"Perfect for our stay in Orlando/Kissimmee. Close to everything we were attending, quiet, clean, and well supplied with the basics."
The price is AU$338
includes taxes & fees
4 Sept - 5 Sept
Beautiful, family-friendly cottage just 4 miles from Disney World
Cozy Lake Cottage - 4 miles to Disney
Private kitchen

Cozy Lake Cottage - 4 miles to Disney

The price is AU$439
includes taxes & fees
25 Aug - 26 Aug
Cozy Lake Cottage - 4 miles to Disney
Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
Pool

Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.

2.0 star property
The price is AU$732
includes taxes & fees
27 Aug - 28 Aug
Caraway Cove Cottage near Disney with Margaritaville Resort & Island H2O Access.
161 - 4 bed Gem at Terraverde Resort
House (4 Bedrooms) | Interior

161 - 4 bed Gem at Terraverde Resort

161 - 4 bed Gem at Terraverde Resort
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
Pool

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

2.0 star property
The price is AU$1,060
includes taxes & fees
27 Aug - 28 Aug
Orange Creamsickle Cottage near Disney with Margaritaville Resort & Island H20.
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Property grounds

Fully-Stocked Cozy Tropical Cottage-4 mi to Disney

The price is AU$405
includes taxes & fees
31 Aug - 1 Sept
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney
Family-Friendly Cottage Near Orlando’s Top Attractions
Interior

Family-Friendly Cottage Near Orlando’s Top Attractions

The price is AU$314
includes taxes & fees
26 Aug - 27 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Dining

Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!

The price is AU$342
includes taxes & fees
31 Aug - 1 Sept
Charming cottage 10 mins to Disney, Pool, Mini Golf, Fitness room and more!
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Pool

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

The price is AU$732
includes taxes & fees
27 Aug - 28 Aug
Crystal Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Sunny Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Pool

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

The price is AU$732
includes taxes & fees
27 Aug - 28 Aug
Sunny 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kissimmee Hotel Reviews

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent
"Awesome experience "
Kiara 1-night trip
Posted 6 hours ago
Holiday Inn Resort Kissimmee by the Parks by IHG

Frequently asked questions

How much do cottages in Kissimmee cost?
Prepare to pay between AU$405 and AU$405 per night for cottages in Kissimmee. Whatever your budget, an excellent stay is only a click or two away on Expedia. This price was 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?
Pack your bags and pick from 1050 cottages in Kissimmee. Thinking about a place where you can relax and stay in touch with nature? Expedia will help you find the ideal escape in a few easy clicks.
What is there to do in Kissimmee near my cottage?
Whatever you're into, Kissimmee has loads to keep you occupied. Discovery Cove, Aquatica and Disneys Typhoon Lagoon Water Park are on most visitors' itineraries. Don't miss Gatorland®, Medieval Times and Fun Spot America either. With Expedia's hotel deals in Kissimmee, you'll be able to see more terrific attractions like these with the cash you save.