There’s a lot you can say about where to stay in Maui, which side of the island is best, which resorts are best for families, for honeymooners, for visitors on a budget, for luxury splurges, etc. and I’ve pretty much hashed it all out on this blog.
I think the Four Seasons is the gold standard, the cream of the crop, the yardstick which all other luxury resorts are measured against…especially in Wailea.
For me, the pool set up wins as overall best. There are three infinity pools plus a lagoon pool and a separate adults only pool over by the spa. One of the infinity pools even has a hot tub in it.
Aesthetically, the Wailea Beach Resort has a modern vibe that’s more in line with the Andaz than the more traditional properties in Wailea (Four Seasons, Grand Wailea, Fairmont Kea Lani) and while it’s definitely a very high end resort, I wouldn’t call it luxury.
I think the Fairmont Kea Lani has the best rooms in Wailea. That is, the best standard price, entry level rooms. EVERY room at the Fairmont Kea Lani is actually a suite with a separate living area and that is a pretty big deal.
Grand really is the best way to describe this resort. It’s one of those places where your jaw is on the ground as you enter the lobby and walk around the property. The architecture, design, and layout is just over the top.