I find it interesting that after a few days there are zero votes for the Disney Hilton Head resort. I guess I may scratch that one off of the contingency list!
I didn't vote, but we've done all the rounds of Disney properties, including Disney Hilton Head last year for spring break - and we loved it! It was an extended family trip with 3 generations, and everyone really liked the feel of the property, etc. The villas were nicely set up, and all of the hammocks, little outdoor games set around the resort, pool area, etc. were all perfect for our group. It's on the water but not the ocean beach, as someone mentioned, but is a quick drive or free shuttle; we did both on various days. The beach house was really nice too - well appointed, with a pool, ping pong, etc., much nicer than I had been envisioning in advance.
But you aren't going to spend that amount there. There isn't a table service restaurant - just one quick service at the main resort and one quick service at the beach house, and I wouldn't recommend them for 3 meals a day, all week (although we did like it - but it's not an extensive menu). They have a few up-charge activities/excursions. We spent maybe $100 total on a bunch of upcharge crafts for my family (champagne painting thing, Mickey burlap wreaths, etc.). The only paid excursion we kept trying to do was repeatedly canceled due to the tide (kayaking), but it was priced a bit less than a cruise excursion. We did rent bikes and spent a small amount in the gift shop. But that's pretty much it.
Long story short, if you were going to split the money into multiple trips, I'd keep it as an option. We'd go back there in a heartbeat, except it's kind of hard to get to if you can't drive. None of us are on the east coast. It's a lot more low-key than Aulani.
