Hubby and I have stayed at the Fairmont x2 when we were young and childless :) We are now taking our 2 kids (14 and 10) back to Hawaii for the first time in mid-June. I am not sure that Wailea is the best area for visiting with children - honeymooners (as we were at the time), yes.
We have the opportunity to stay at the Grand Wailea using Hilton Honors points for half of our 6 night stay. Hubby is ALL about the GW - amazing pool for the kids, we're familiar with the area, enjoy the walkway between hotels... I'm not so sure. Review are saying the rooms look "tired," nickel and diming you for everything, and food is meh. My family also enjoys playing on the beach - swimming, building sand castes, etc - not sure the beach here is swimmable? My fear is that if we book using points, we'll get a room that reflects that, instead of one that a paying customer would receive.
On the flip side, we have the option to stay at the Westin Kaanapali Ocean Resort Villas in a 1BR, Island View room (no points). I know it has a pool and a slide, and appears to have a really good beach that's ideal for snorkeling and swimming (and sand castles). We have never stayed in Kaanapali, but we have spent time checking out the coves towards Kapalua for snorkeling. I don't know if we would receive a North room or a South room (and honestly don't think it much matters, since it's an Island View either way, and we're non-owners).
I think my hubby is enamored with the idea of going back to Wailea (champagne taste on a beer budget!), when the kids are going to want to hang out at the beach more than anything (many vacations to Grandparents in Cape Cod has proven this to be the case....).
Am I crazy to pass up the GW? (!) Is it better to be closer to Lahaina for meals/activities with 2 kids in tow?
Should add - we are spending 5 days prior to Maui on the Big Island, staying at Hilton Kings Land with access to the gigantic pool complex at the Hilton Waikoloa.