In the New York Times, Christopher Percy Collier describes kayaking the shallows around the lower and middle Florida Keys. He lists a number of kayak rental places along U.S. 1 where, as he says, "finding a kayak outfitter has come to be about as difficult as spotting a pelican." Add finding a bar to the same list.
There are plenty of bonefish flats that are accessible via kayak, if you know where to go, or just care to do some exploring. My advice: stay near the mainland and look for light colored bottom either north or south of the highway. Without the advantage of height, you'll need all the help you can get. Speaking of which, if you really want to see fish anywhere in the Florida Keys, hiring a guide and fishing from a skiff is your best option. Because of the lousy economy, plenty of top guides who would otherwise be booked for the entire year already are going to have openings here and there. It's a great opportunity to get some recurring dates.
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