Kissimmee cottage rentals

We found 264 cottage rentals — enter your dates for availability

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any cottage rentals in Kissimmee?
Pick from 264 cottage rentals in Kissimmee that offer a quiet, cosy retreat amid the sights and sounds of nature. Check out cottages in sought-after neighbourhoods such as Historic Downtown Kissimmee, Mill Run and Magic Landings.
How much does it cost to stay in a cottage rental in Kissimmee?
Check out our cottage rental listings in Kissimmee for an idea of costs. If you want to make some savings, use our "Discounts" filter. It'll show you any cottages with special deals, whether that's a monthly, weekly or new listing discount.
When is the best time to rent a cottage in Kissimmee?
Consider taking a trip to Kissimmee in March, when average daily temperatures range between 15ºC and 25ºC. This is the most popular time of year for guests to stay in a cosy cottage rental in this well-known destination, which is located in Orlando.
Where can I rent a Kissimmee holiday cottage with great views?
When searching for your cottage rental in Kissimmee, make use of our "Location" filter. This lets you choose the sorts of areas you prefer to stay in, whether that's around nature or somewhere more central.
Does Kissimmee have any lakeside cottages?
Stunning views of glittering water, the beauty of nature and outdoor pursuits are just some of the things to enjoy in one of Stayz's lakeside cottage rentals. Try out our "Location" filter and check the "Lake" box to see if there are any cosy retreats in Kissimmee near the water.
What are the top things to do in Kissimmee?
Disney's Animal Kingdom® Theme Park, Orange County Convention Centre and Epcot® are top-rated attractions that'll keep the whole family busy in Kissimmee. There's nothing like travel to get everyone together, so check out our cottage rentals in this vibrant destination.
Why should I book my holiday cottage with Stayz?
With Stayz you'll never have to share your cottage rental with strangers, whether you're looking for a rustic stay in the mountains or a swanky pad by the beach. Another awesome thing about booking with us? You can filter your search by nightly price, amenities and more to find a cottage rental that matches your style and needs. Our flexible cancellation policies and first-class customer support also ensure a hassle-free trip.