Ho'olei At Grand Wailea

As much as we love a short term rental, they can leave a lot to be desired: namely, the confidence in knowing you’re heading to a truly pampering stay with all the activities and doting staff you’ll need for a topnotch trip. Ho’Olei at Grand Wailea combines the homey feel of a private villa with everything one could want from a resort, and the villas themselves are megawatt. Each is a minimum of 3,400 square feet, with 3.5 bathrooms, prime panoramas over the ocean and verdant gardens, and the ability to sleep up to 8. But our favorite thing might be the kitchens, so well stocked they would satisfy Ina Garten herself…and the perfect place to whip up whatever you’re craving, at any hour.

A collection of luxe villas overlooking the lush mountains and surrounding seas, with fully tricked out kitchens and private lanais.

Lacking the resort experience. Head to Grand Wailea to indulge at the new spa and nine restaurants (including a grotto bar, where you’ll sip cocktails in a cave).

You’re on a health kick and can’t eat out for every meal, so the fully equipped kitchens are a dream come true. That they overlook a turquoise span of Pacific Ocean is just a bonus.

You’ve spent the afternoon dipping your way through the 770,000-gallon activity pools, all connected by a “river” of whitewater rapids. So you’ve more than earned your drink in a cave at the Grotto Bar: a Mai Tai, of course.

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