We just came back from our first trip to HH on Sat. We stayed 5 nights, and drove there from Chicago. Our first contract was at HH as a resale since I thought it would be a great place for dh and I after the kids got older. We got a good price and it was loaded.
We loved the resort, but surprisingly we didn't love the vacation as much as I thought we would. Don't get me wrong, I loved the resort, location, villas and many of the hotel activities. It's just that we realized that we are not beach people, and I have a hard time spending hours at the pool. The difficulty for us is that we have three kids under age 7 with the youngest being only 20 months. At WDW, there is always something to do or somewhere to go with a little pool time thrown in for the kids. At HH island, there are lots of great outdoor activities, but they're not great for young kids. Dh and I would have loved to go hiking, on a long bike ride, or to explore some of the shops. Our kids are too young for these activities. We went on a couple of bike rides, but dd who is 7 could only go for a couple of miles. The nature stuff is not interesting to them yet, and none of them really liked the beach for more than about an hour tops. We spent a majority of the vacation in the main pool which dds liked, but I got bored with.
I know we will love a HH island vacation one day. Our plan is to go again in about 3-4 years when dd3 is 4-5 and our oldest will be 10-11. At that time, they will be able participate in more activities, (including the kids night out), and hopefully will be more interested in the beach and other outdoor activities.
This was just our experience with our family this year. The resort is fantastic and I'm sure will be a family favorite soon. (And BTW, dd1 said she liked HH better than WDW, but that's because she would live in a pool if we let her). Hopefully, I'll get a TR together soon. It was a fun week, it was just so different than being at WDW which I felt like I missed while we were there.