Re the ladies I'd put out an ISO on the Florida Board. Re places to stay there are a TON, but you'll need to say what your price range is to get any meaningful help.
You need to import whomever you plan to have fun with.
As for where to stay, I'd suggest a nice B&B near Duval Street, which is the main drag. In season, expect to pay around $400/night. The Heron House on Simonton is very nice. You can get cheapo motels for about half that but it will be a long hike to Duval from them. I've been going to KW just about every year for the last ten years.
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