I don't know how your kids are or how you are. I don't mean that in a bad way just that do your kids, spouse and yourself like to travel around or lounge by the pool? One option could be to spend a week up in Kaanapali and then a week down in Wailea. You would almost get to different experinces. Which resort in Wailea are you staying at if I may ask? Also, are you getting two rooms or a suite? Over in Kaanapali, maybe a two bedroom condo would do nicely. There are a couple that are right on the beach. I just stayed at the Kaanapali Alii. I had a two bedroom, two bath that was ocean front. It was expensive but it was school vacation. It was a really nice, high end condo. Any other questions please ask.