Great idea for a thread!
Any time I hear I'm Yours by Jason Mraz, I feel like I'm sitting by the adult pool. Also, many of those sail away party songs bring me right there. Off the top of my head I can think of, Dynamite, Timber, and Moves Like Jagger. On the rare occasion I hear I Need A Hero, I can just picture Mickey swooping in to save the day at the Pirate Party.
As for CC, Come Monday and A Pirate Looks at 40, that we usually hear at the Heads Up Bar, and I Can See Clearly Now, which we often hear around the island.