Have you looked into Sun City Center, between Tampa and Sarasota, just off of I-75 Ruskin exit. I have a friend living there, he hated it in the beginning but once he got involved with the activities and amenities you have access to, he loved it and was always talking about how great it was living there. He actually live in Kings Point, a gated 24/7/365 by volunteers of the community, 2 clubhouses, the main clubhouse always have something to offer, classes on how to's from crafts to computer courses to jewelry making, plus trips out of town all the month all on their own private buses. it is a golf cart friendly community that you can drive out to local shopping, wal-mart, Publix, Winn-Dixie, pharmacies, home improvement, retail and dining. Prices vary, depending on what you're looking for, most all include cable, association fees, water, basically you just pay for the electric and rental. Most rentals are not set in stone, spring is best time to look, prices usually cheaper and you have more bargain power.
Hope this shed some light on your search, noticed you are from Kissimmee area, I live in Winter Park and drove to Sun City in about 1 hour 20 minutes with no delays and within the speed limit. Sun city is about 1 mile east of I-75 S.