I Pricelined a 1* at $41 in KW itself (a block from Duval St, toward south end). Old, damp motel affiliated with a more expensive place nearby. The real jaw-dropper was that the 1* place charged at $10/night mandatory "resort fee," making the real total $51+ taxes +junk. At the time the Comfort Inn and another place on the other end of the island (near the bridge) were going for $55+. Of course, this is midweek if no events happening.

Generally, though, it's hard to get deals, though you often get a dollop of attitude thrown in for free. I remember back around 1987 the area still had some shabby-alternative cred, but today it's all "gingerbreaded" (i.e. renovated to give curb appeal, but in a very commercial way), and the cruise ship passengers will overwhelm the place. No wonder many of the locals are grouchy. And David Allan Coe points out that Jimmy Buffett sure don't live there anymore.