I did the advanced race seminar there in March 2006. J World gave me a list of places to stay. The Cypress House Bed & Breakfast is within walking distance of the J World school and was very reasonable. Contact info is available at the link. They had a happy hour there every day with quite an assortment of drinks and food. Some of the J World instructors would crash that.

If you haven't been to Key West before, stand by for the "cultural enhancement".