Where in the Keys are you staying?
I've never been to a dive shop actually. LOL Most resturants in Key West are pretty good, and there is a TV channel that will be in your hotel room, or where you stay [it is one of only 3 local stations] that shows commericals of a lot of resturants you'd want to consider and even places you might want go to [Key West only].
Sept is not a good time to visit the Keys, however, as Aug and Sept are our big hurricane mos. Not unusual for an evac to be ordered and tourists are the first to be asked to leave! Even if the storm doesn¡¦t even get here! Because we are tiny islands with only 1 way in and 1 way out, orders in regards to evacs are usually given days in advance. That would be a real downer. Being stuck in a hotel room with no electricity is even a bigger downer. Predictions with the National Hurricane Center this yr says it is going to be a busy season for us...but, you never really know.
Hotel prices in Key West will be steep. If you are staying up the Keys, you can probably find something more affordable, and, maybe even more enjoyable. However, summer prices are better. do you want luxury? or standard chains? There are a good many guest house, B&B's in Key West. Resorts and a lot of the chains. Expect to pay more than you would expect even for a chain hotel.
You might want to go up to John Pennekamp State Park, Key Largo. big reef, dive shop, boating, etc., located in all one place. The beaches: Fort Zackery Taylor and Bahia Honda State Park. Other Key West beaches are the pits. If you like to party, then Key West would be the place, closer to down town [Old Town] the better. That area of town is geared toward catering to tourists, but with plenty of local activity and "color" as well. No LFS here!
There are a lot of tourist sites on the area on the
www. Check 'em out!
But, if it were me, I'd go to Disney World.....lol