this one is easy:

Caneel bay on St. Johns in the US Virgin Islands

http://www.caneelbay.com/
http://www.azurecollection.com/caneel_bay.htm

by far, one of the nicer places i have been. watch the timing because you are in the carribean (hurricanes possible from june to oct... none to speak of for the last 2 years, though). cost is moderate ($200-300/night/person) but low compared to NYC hotel prices.

St Thomas is right there, which i believe has gambling if you are so inclined. glass bottom boats, scuba, steel drum bands... and your villa is on the sand. just... awesome

whatever you do, if you are looking to make it nice... you cannot go wrong with the Rosewood Hotel & Resorts

http://www.rosewoodhotels.com/

the one place i wanted to try, but haven't yet... was Little Dix Bay on the British Virgin Islands, also a Rosewood location

http://www.villasatlittledixbay.com/