Photo by Sophia Hatchitt

Kissimmee rentals with pool

We found 29,162 rentals with pool — enter your dates for availability

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  • More quality time

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  • 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 holiday rentals with a pool in Kissimmee?
Book one of our 29,162 holiday rentals with a pool and start making plans for your Kissimmee trip. Whether you'd like to be in Historic Downtown Kissimmee, Mill Run, Magic Landings or another much-visited neighbourhood, you'll discover the perfect poolside property on Stayz.
How much does it cost to stay in a holiday rental with a pool in Kissimmee?
Prices vary depending on season, length of stay and specific location, so enter your travel details to find a property offering a splashing good time. Whatever your budget or plans, Stayz has holiday rentals with a pool in Kissimmee for every type of guest.
When is the best time to book a holiday rental with a pool in Kissimmee?
Consider booking your poolside retreat to Kissimmee in March, when average daily temperatures range between 15ºC and 25ºC. This is the most popular time of year for guests to get a holiday rental with a pool in this destination, which is located in Orlando.
What holiday rentals with a pool in Kissimmee have nice views?
When searching for your holiday rental with a pool in Kissimmee, use the "Location" filter. This lets you choose the types of areas you prefer to stay in, whether that's around nature or somewhere close to the action. Pick your favourite and remember to pack your swimwear.
Are there holiday rentals with a private pool in Kissimmee?
From making whirlpools with the kids to moonlit swims, a holiday rental with a private pool offers plenty of possibilities for fun and relaxation. If you're visiting Kissimmee, use our "Private pool" filter to look for properties that come with this exclusive amenity.
What are the top things to do in Kissimmee?
Disney's Animal Kingdom® Theme Park, Orange County Convention Centre and Epcot® are places to add to your itinerary while staying at a holiday home rental with a pool in Kissimmee. The only thing that beats discovering this city's leading attractions? Chilling out poolside with the crew after a busy day of tours and activities.
Why should I book my holiday rental with a pool with Stayz?
No sharing your space, no awkward encounters with people you don't know. When you stay in a Stayz holiday rental with a pool, you'll have the whole place to yourself to have a splashing good time. Need to amend or cancel your travel itinerary? Our flexible cancellation policies mean you're able to book your rental house with complete peace of mind.