Perched 300 feet above the Pacific on 15 verdant acres, Hotel Wailea is a former members’ club that still feels like a hidden enclave of cool. In 2014, new owners invested $15 million in a redesign that left 72 one-bedroom suites with white oak floors, Sub-Zero appliances, and Hawaii-inspired art. Still, it’s the pool that really wins over guests—it’s calm and quiet (thanks to the hotel’s no-kids policy); there are umbrella-shaded loungers and bungalows with fans for when you’ve had too much sun; and the beyond-gracious staff are always at the ready with water, cocktails, kombucha, and coconut water. The hotel lounge offers free wine and appetizers at 5 p.m. on Friday nights, while the farm-to-fork restaurant highlights produce grown in the resort’s own garden. Complimentary on-site activities include yoga, outrigger canoeing, and mixology classes, but guests can take the hotel’s Tesla Model X house vehicles anywhere in Wailea or rent an electric bike and cruise the South Maui coast if they want to get off property.