What we think

Skylark only includes hotels that meet our stamp of approval. Our editorial review for this one isn’t ready yet — but we’re working on it! Below is the hotel’s own description.

Discover a blissful, breezy retreat on Maui's southern shore at Ho'olei at Grand Wailea. The neighbor of Grand Wailea, a Waldorf Astoria Resort, this private enclave blends residence living and resort amenities for the ultimate home away from home. Each of our two-story luxury villas features three bedrooms, three bathrooms, a lanai (balcony), full kitchen, private elevator and garage - perfect for a family getaway or destination wedding. Find the best of both vacation worlds at Ho'olei at Grand Wailea. Enjoy a laidback stay and peaceful Hawaiian living in our spacious luxury townhomes. And when you're ready for adventure, take our shuttle to the Grand Wailea resort for all the amenities and experiences you're looking for on a tropical getaway. Our resort in Hawaii offers access to a wealth of activities, whether you're here with family, on a work retreat, or simply feeling indulgent: sparkling pool with sandy beach entry, plus waterfalls and a children's pool, award-winning spa for pampering treatments, massage therapy and couples packages, free SCUBA lessons for ages 12+, and unlimited access to kayaks and snorkeling equipment, 8 restaurants and bars, all with distinct menus and panoramic views, 3 golf courses with tropical landscapes and the only David Leadbetter Golf Academy in Hawaii, award-winning event space, including elegant ballrooms and sunny waterfront gardens.

Restaurants & Bars

Humuhumunukunukuāpuaʻa - Savor artfully crafted Hawaiian cuisine and stunning Pacific views

Molokini Coastal - Delicious dishes reflecting classic American flavors and Mediterranean influences—all made with sustainable ingredients sourced from local farms

Café Kula - A fresh array of gourmet takeout items inspired by the farm-to-table movement

Aloha Trick Pony - Satisfy your gourmet food truck cravings with delicious Magical Tacos and fresh ‘ahi poke bowls

Wailea Surf Haus - Walk-up beach bar just steps from the surf