Ok - Cypress Dunes is beautiful but there is no beach access. The others are ok but I think you will find Watersound West Beach a perfect fit for all. Option to join beach club includes Golf at 2 courses. The beach is a 10 minute walk or quick bike ride and the most beautiful we've seen. The Beach Club has gorgeous beach, too, and bar/restaurant w huge pool.
Plus, prices are reasonable but already starting to creep up. Good investment !
Kurt is right. First you need to decide on townhouse, condo, or house.
I know someone who lost a million dollars at Cypress Dunes due to no beach access. If you can get a house there for the $500's or below, that would be a good deal. You'll have to drive or trepass on state park property to get to the beach.
The named resorts are popular for those who like a homogeneous neighborhood with not-so-private beaches. But the HOA fees are outrageous in comparison to the neighborhoods that aren't named resorts. For example, our HOA fees in Seagrove for a large home in a low density neighborhood 1 minute from a very private beach and south of 30A are $800 a year. Compare that to up to $3000 a quarter for the named resorts. You need to factor that into your costs.
As far as the named resorts go, you also need to make the walk and bike ride down to the beach from the property in which you are interested on a hot day. You need to know how miserable and buggy that would be at certain times of the year and how far you'd be from a bathroom. And are there bike paths all the way to the beach, or is your family going to have to be subjected to sharing the road with vehicles on the "short" ride to the beach?
As far as WSW goes, you have to pay a premium on top of your HOA fees at WSW to use the amenities at the "main" Watersound mentioned by vcalhoun such as the beach club, the golf courses, the Watersound pool, and the Watersound beach.
Just basically you need to have your eyes wide open.