For Tropical Storm force winds to occur in Key West, with a radius of 205nm. Dean would have to pass over the Isla de Juvidad-Isle of Youth, or just to it's west.
Something strange is going on with Dean...
A Major Hurricane with 145mph winds should be more symmetrical than Dean is. The latest IR loop from GHCC shows some strange Vortice swirls spinning off of the Eye. http://wwwghcc.msfc.nasa.gov/GOES/goeseastconusir.html