Built on the site of the old Kapalua Bay Hotel, this 24-acre compound offers just 50 impeccably furnished rental residences, from one-bedroom to four-bedroom (1,250–4,050 sq. ft.). The low density—and astronomical prices—means there’s never a crush at the terraced Sunset Pool with gorgeous Lanai and Molokai views, or the more intimate infinity-edged Beach Club Pool, or anywhere else on the beautifully landscaped grounds. It’s hard to leave the cocoon of the roomy villas, which offer gourmet kitchens, high-end linens and robes, spa-like bathrooms, and lanais or balconies with massive daybeds. Still, you don’t want to miss the chance to “talk story” with cultural advisor Silla Kaina over lei-making, ukulele classes, or another of the free Hawaiian-themed activities. (Look for Kaina’s portrait by local artist Pegge Hopper, supplementing the series she did for the Kapalua Bay Hotel.) The 30,000-sq.-ft., two-story Spa Montage Kapalua Bay includes a vast fitness center with a raft of weekly classes, infinity-edge pool, and well-stocked boutique. The open-air restaurant Cane & Canoe epitomizes most of the culinary offerings at the resort: expensive, not particularly exciting, but satisfying enough and graciously served. An in-room poke-making cooking class (among others) with Executive Chef Chris Damskey, however, is an exceptional experience, as is renting the Cliff House overlooking Namalu Bay for a private meal. Note: It’s hard to believe at this price level, but room rates do not include the $48 daily resort fee.