There is also one in the little shopping center that houses Winn-Dixie, on S. Apopka Vineland Road. It's not Kissimmee, but Orlando technically.
It's called NY Smoke Shop. If you leave Downtown Disney and make a left onto Hotel Plaza Boulevard and follow that to the end/traffic light. Make a left onto S. Apopka Vineland Road. About 1 or 2 traffic lights down, on your right, there is a small plaza, right past the ABC Liquor Store. The shop is in there and the prices are very reasonable. Not sure how much they have in the way of cigars since I never really paid attention buy my husband buys cigarettes there, very cheap. Here's a number, you could probably call them ahead of time and ask.
11945 S Apopka Vineland Rd
Orlando, FL 32836
(407) 239-9900