Originally Posted by DJ_Iceman

Of course opinions vary, but I've spent quite a bit of time in Wailea so am happy to share mine. My go-to place is the Marriott, as I find it offers the best value. The staff is great, it's right next to the upscale Shops at Wailea, the adults-only infinity pool is a delight, and I always get great upgrades as a Marriott plat.

I also used to stay at the Andaz years ago when it was the Renaissance (and therefore part of the Marriott family). I wandered over during my last stay in June and found it stuffy, pretentious, poorly laid-out, and generally disappointing. It's trying SO hard to be hip and cool that it was almost painful to watch.

The other place I don't care for (but many of my friends do) is the Waldorf=Astoria Grand Wailea. It's always been a bit of a circus, but they've let the place get run-down over time so now it's not even the sparkling circus it once was. My Hilton buddies complain about their lack of upgrades or elite treatment in general, but keep going back because at least they can earn points. And at the inflated prices the place charges, they do earn a lot of points.

I do, however, like the Fairmont. It's an all-suite layout and offer Fairmont's typical high level of service and amenities. The location is relatively poor, being all the way at the end of the Wailea beachwalk, but otherwise it's a good, solid choice.

The Four Seasons gets mixed reviews. I do think they charge more than what their rooms are worth, and you have to pay for a decently upgraded room to get even a hint of ocean view. I also had a very disappointing meal at Spago in June, when my wife and I ate there for our 20th anniversary based on the Beverly Hills Spago being one of the best dining experiences of our lives. But you can't judge the hotel just based on that.

If you're willing to forsake points, there are all kinds of timeshares and condos for rent up and down Wailea beach that probably offer a much better value proposition. But since you're posting here you probably a points-chaser like the rest of us, so that may not be a viable option. Good luck finding a room when you want to go, and please report back on what you pick and how you like it!

Oh, and I forgot to mention that the Sheraton in Ka'anapali is a pretty poor place, but the Westin looks wonderful. The Ritz is fantastic, but more remote and some people here have complained about cloudy days and rain up on that corner of the island. I only stayed up there once, and it was just as perfect as my many stays in Wailea so I can't vouch for the weather!