Clothing/Shoes/Weather Gear: When it comes to the weather in the greater Tampa Bay area, summer is the norm. Make sure you bring clothes for warm weather as you are almost guaranteed several temperate days. Toward the end of October, however, there are a couple days that might actually fool you. On the night before I flew it, it dropped to 62! It was quickly back up to 75 the following day, but make sure you bring a windbreaker just in case for the evenings or a cold day.
Shoes??? Forget about it!
Toiletries and Medical Supplies: Bring sunblock from home or pay a small fortune here! If you are the type to not care too much, I highly suggest bringing along a lidocaine based gel to soothe your poor burning skin! Store it in a refrigerator for greater relief when applying it!
Camping/Beach/Outdoor Gear: If you are vacationing with children, check with the hotel about a beach umbrella. Many vacationers buy them here and leave them for someone else to use. I think it is important for a child to take a break from the sun once in a while. Maybe you'll get lucky and they'll have some sand toys, too!