We prefer the south shore, specifically in the hills overlooking Chocolate Hole. Key villa criteria for us include a pool, that we have wide distant views (so we like to be a bit higher up) and a generally south to southwest facing villa orientation for uninterrupted view of the sunset to the horizon. Others might prefer to have sunrise views. From this area you're a 7-8 minute drive into Cruz Bay (very convenient if going to town for dinners) and less than 5 minutes to the market just outside the Westin Resort or to Starfish Market. It's about 25 minutes to Francis Bay and Annaberg Ruins on the north shore, and less time to Trunk Bay or Cinnamon Bay. There is also a pretty large selection of 2- and 3-bedroom villas at "reasonable" prices on the south shore. I've not researched it much, but it appears the villa rentals in the Coral Bay area tend on average to cost a bit less. If money were no object, I would love to stay in the upscale villas at Peter Bay. I suggest going to VRBO.com to start your search.