We were just there in June and already have 3 days reserved for next June. We try to open up a few days before or after our week in Maui at either WKORV or MOC to spend at the Grand Wailea. I booked next year in points and it cost 240k in points at 80k a night which sounds like a lot and it is, but Hilton points are only worth 1/4 of SPG points and generally easier to build up.
The Grand Wailea has so much to offer and truly is a "resort". They have multiple pools on different levels most of which are linked together with slides and mini rapids. There is a water elevator that is truly unique that takes you from the lowest pool all the way up to the highest pool in a sealed chamber and basket where the chamber is filled with water that floats the basket carrying around ten people to the top so you can start your fun all over again down to the lower pool. There is a lazy river to float around in. There is a grotto to get some snacks and cocktails. And my kids favorite is the Tarzan rope swing where they can spend hours jumping off the ledge screaming crazy slogans and trying to backflip off the rope. Loads of fun!!!
In the many times we have been there we have yet to step foot on the beach there but from what we hear they offer chaise lounges and umbrellas for guests. Each time we go to the Grand Wailea we tell our selves we have to check out the beach but we have so much fun at the resort we just never find time to do that, plus we usually spend most of our time at the beach when we stay at our other TS resorts. We come to Grand Wailea to enjoy the resort and the pools water features.
If possible I recommend upgrading to the Napua club level. Being Hilton Honors Diamond does not automatically upgrade to the Napua Level but it is possible to pay for the upgrade and it includes an exclusive wing that requires card access, with decent breakfast, afternoon tea and cookies and evening hors d'eouvres with cocktails with very generous pours.
We can't wait to get back there!!!