Hi there! We are also looking into where to do our Reception dinner for our Key West wedding. Rooftop Cafe and Conch Republic are both top spots on my list. I have eaten at both and they are both very good. I've heard about Louie's. Not sure about Rum Barrel. One spot i really wanted to look into was the Crowne Plaza. They have an awesome Rooftop view and fun happy hours with amazing sunset views. Not sure how expensive it would be though.With such a small group you could go to any restaurant really. Margaritaville is so touristy, i would avoid it.