You should really consider Puerto Rico. Beautiful warm waters and great surfing especially in the winter months. Rincon on the west side of the island is becoming quite the surfer's mecca in the winter months, but places book up quickly.
The east side of the island is great for beginners as there is a sand bottom beach so no worries about rocks and reefs and the waves are not overpowering.
There are also many great guest houses/B&B's to choose from on the island which may be a great way for your family to enjoy the island.
Go to the Puerto Rico forum search Rincon for information on the west side and look at the El Yunque section for information on the east side of the island.
