Spent a couple of days in Key West about a month ago to use the Kite House. I highly recommend "Popular Guest House". My friend and I ended up paying about $100/night but it was well worth it. First, you are doors down from the Kite House guys....it includes an unbelievable breakfast...and you are walking distance from the main strip. Have a great time! Check out my pictures from kitesurfing down there....
http://picasaweb.google.com/pramco/KitesurfKeyWest
you will love the flats where they take you...clear crystal water and shallow (below the waist). Have a blast then tell us about it!
http://picasaweb.google.com/pramco/KitesurfKeyWest