Kissimmee is home to a 650-person capacity outdoor water park, in addition to multiple golf courses.

Kissimmee is also home to the Loop, a large outdoor shopping mall at John Young and Osceola Parkways on the Orange/Osceola County line. It features stores such as American Eagle, Kohls, and Best Buy. There is also a multi-plex theater.

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Osceola Heritage Park is an event facility featuring a concert arena (Silver Spurs Arena) and professional sports stadium (Osceola County Stadium). The Silver Spurs Arena has been host to many acts, ranging from Hilary Duff and Bob Dylan to an annual rodeo event. Jehovah's Witnesses also use The Silver Spurs Arena for their annual District Conventions. In 2008, a number of English and Spanish conventions will be held by the Witnesses, bringing thousands of delegates to the Kissimmee area for the three-day events.

The Houston Astros conduct spring training in Kissimmee, at Osceola County Stadium. The stadium also hosts numerous amateur baseball events throughout the remainder of the year in conjunction with; USSSA, Triple Crown Sports, World Baseball Federation and Promotion Sports. The Jim Evan's Academy of Professional Umpiring has also called Osceola County Stadium home since 1994.

The Osceola County Softball Complex is a facility of five (5) softball fields which are host to a variety of amateur sports events. It is the home of the USSSA 2005 Complex of the Year Award, the Rebel Spring Games, and numerous other fast-pitch softball, slow-pitch softball, and youth baseball events.

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