I have been to HH in early November and it really isn't ocean swimming weather then. We were able to wade a little on both trips, but there were no lifeguards or anything, and not to many others in the water. There are a lot of activities at HH. Some free, such as Goofy Bingo, beach tours, nature tour, bedtime stories (with great cookies and milk) and the Campfire (with singing and smores) and others that cost, such as the tea party, and fish print tee shirts, dolphin tours, and nightouts for the kids, etc. We love it there. There is shopping within walking distance, you can rent or bring bikes. I compare it to the best campground experience you can have with the resort accomodations. You can fish or crab. The island has some good restaurants. The pool is heated so we were always in there no matter how cool it was out, not sure about Christmas. I'm sure they would have extra activities for the holiday. We are never board there, but can also find time to relax. Never stayed at VB, but would expect the weather to be warmer there, but also variable. More like Orlando in Dec. Good Luck!