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Most of us know a bit about the island of Maui, whether it’s from television, movies or personal experience. There’s something for everyone on the island, including day-trippers coming off a cruise to folks looking for a laid back party scene to those seeking completely remote areas where they can hang with locals. And then there’s Wailea, for those looking for some next level Maui, and which also happens to be one of my personal favorite places on the island and in the world.

Wailea is most definitely the affluent part of Maui, with some of the best luxury resorts all taking prime real estate on the coveted beachfront. The Shops at Wailea, the premiere shopping within, boasts retailers such as Gucci, Prada, Louis Vuitton, Tiffany & Co., and many other upscale brands (as well as some more affordable surf shops). The dining scene, mostly due to the top hotels, has exploded and reservations can be hard to come by during peak times. Cocktail culture has also cemented itself within Wailea, and mixologists aren’t afraid to step outside of the typical tropical concoction we are most accustomed to when we think of the islands.

Through my writing, I’ve been fortunate enough to experience Wailea more than a dozen times in recent years, and have typically spent time there with friends and family. It’s become a home away from home and through the luxury resorts, I’ve discovered the villas that each resort has available to their guests, making my time there even more over the top and glamorous. Below are the three top villa products in Wailea as well as a fourth option for times when our wallets aren’t as thick as we’d like them to be.

Ho’olei at Grand Wailea, A Waldorf Astoria Resort

Located adjacent to Grand Wailea, these private two-story two and three-bedroom villas feature finely appointed interiors with a modern kitchen, private elevator, attached one-car garage, and exclusive services. Ho'olei guests also have access to Grand Wailea's property amenities, including pools, waterslides, kids game room, restaurants, and shops. A stay here also comes with a dedicated concierge and on-site security, private interior elevator, deep soaking tub, fully stocked laundry room, sub-zero refrigerators and a private grill.

When I first pulled into my private garage and found myself on the bottom level of my two-story villa, with an elevator, I might have pinched myself a few times before I realized this was truly a real place. I was visiting with a group of friends and their kids, but since the villa was gigantic, space was never an issue. The entryway was my favorite though, as it led into an oversized kitchen and living room with a balcony that could fit a large group of friends. We were there during the Super Bowl, so, of course, I took advantage of the space and invited all my friends over for a party…the place is made for entertaining, to say the least. Although it’s not beachfront, it’s a very short walk across the street to the main resort as well as the beach. But the truth is, we loved the space so much, it was hard to find time to leave it. Ho’olei was the largest of all the villas I experienced, and the one that felt most like a home.

Fairmont Kea Lani

Steps from Polo Beach, the Villas at Fairmont Kea Lani resort are ideal for family or multi-couple Maui beach vacations. Two and three-bedroom villas offer 1800 and 2200 square feet of living space, featuring a full gourmet kitchen with dining area, two master bedrooms (each with an oversized Italian marble bathroom), full entertainment system with flat screen TVs, and a private furnished courtyard with plunge pool and barbeque grill. Villa guests receive premium amenities including complimentary valet parking, daily buffet breakfast, and a welcome basket filled with tropical fruits, Hawaiian jams, freshly baked banana bread, cream, milk, butter, snacks, and Ocean Vodka. Chilled waters and tropical juices are refreshed daily.



My most recent trip to Wailea included a stay at the Fairmont and I was very excited to experience their villa product with my sister. Ours was oceanfront, and from the moment we walked in, we raced to explore the top level. What we found was a very large master bedroom along with a gigantic bathroom. Being the gentleman that I am, I insisted that my sister take it, without even seeing the rest of the space. As I walked down the steps, I saw an expansive living space that led to a patio with a plunge pool and views of the ocean. Entering the second bedroom, I realized it was another master bedroom layout with the same gigantic bathroom, and this one was conveniently located next to the kitchen, so in the end, I had unknowingly positioned myself in the better of the two bedrooms, since I had direct beach and kitchen access.

Andaz Maui at Wailea Resort

Situated on Maui’s premier southwestern coastline and just steps from the sands of Mokapu Beach, Andaz Maui at Wailea Resort has various residential style villa products. The 3,234 sq. ft. villas at Andaz Maui at Wailea Resort, with up to three bedrooms, offer a secluded tropical hideaway with authentic modern touches such as private lanais for admiring magnificent Maui sunsets, baths with ocean and garden view showers, as well as luxurious bath amenities that invigorate body and mind. Designed by the award-winning architecture and design firm Rockwell Group, the villas boast a contemporary Andaz signature style while successfully capturing the spirit of the Hawaiian Islands. 

Without a doubt, the Andaz is the most contemporary of the three villas and staying there made me feel like a million bucks. The clean lines of the design coupled with the modern and minimalist furnishings and floor to ceiling windows, made this place feel ultra hip and well, expensive. My family and I spent the pre-holidays here, and we made use out of the kitchen and living space, including the outdoor BBQ. There were many moments where I found myself laying on a couch, just enjoying the ocean breeze as the doors to the outside opened up to create an indoor/outdoor living experience. This one truly felt like the home I dream of having one day, or at least the home I’ll always fantasize about having, so I made sure to spend adequate time in each room daydreaming, including the den (which I converted into my office).

Approachable Luxury

Hey, listen, we can’t always have villas or 5-star resorts, especially in an area that’s dominated by them. If #VillaLife is too far of a stretch of your financial reality, consider the Residence Inn Maui Wailea, the first of its kind in the typically costly Wailea. This place is truly the first affordable big box option in Wailea and I had the opportunity to stay there, and it was pretty awesome. Located just across the street from the beach, and walking distance (although they have free shuttle service to any destination within Wailea) to the Shops at Wailea, among other places. Each unit here comes with a kitchen and sizeable living space, so it’s kind of a mini-villa, but located alongside many other mini-villas, like a hotel, because well, it’s a hotel.  


David Duran
David Duran has traveled to all seven continents and more than 70 countries during his span as a world traveler who writes words.