We are looking at doing the exact same thing, possibly Islamorada. Funny thing is I had already requested info about the property inanna stayed at before seeing these posts. Our biggest problem is finding a beach house that can handle an outdoor party the size we want (100). I really hope we can figure it out.
A big headache we've found at the resorts is they want to charge an exorbitant amount for bar service and liquor costs. And you have to buy all your liquor through only them, and no cash bar, etc etc. I just get tired of all the rules that force you to pay up.
Inanna, I sent you a pm, hope you get it.