Kissimmee rentals with pool

Book one of our 28,015 vacation 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 neighborhood, you’ll discover the perfect poolside property on Vrbo.

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, Vrbo has vacation rentals with a pool in Kissimmee for every type of guest.

Consider booking your poolside retreat to Kissimmee in March, when average daily temperatures range between 59ºF (15ºC) and 77ºF (25ºC). This is the most popular time of year for guests to get a vacation rental with a pool in this destination, which is located in Orlando.

When searching for your vacation 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 favorite and remember to pack your swimwear.

From making whirlpools with the kids to moonlit swims, a vacation 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.

Disney’s Animal Kingdom® Theme Park, Orange County Convention Center and Epcot® are places to add to your itinerary while staying at a vacation 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.

Whether you’re traveling as a couple or with the entire crew, staying at a vacation rental with a pool promises another level of relaxation and fun to your break. And with our flexible cancellation policies, if you have to change plans, you’ll get a complete refund as long as you cancel within the time frame stated by the property owner. On top of all that, our One Key™ rewards program lets you earn OneKeyCash™* on all eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.