Culture / Travel

Becoming a Maui ‘Homeowner’ (Even if it’s Only for a Vacation) — Luxury Hawaii Residences Often Beat a Hotel Stay

Living Large in Your Own Island Retreat

BY // 11.01.19

MAUI, Hawaii — When visitors arrive at the vacation behemoth that is the Hawaiian island of Maui, the question that is inevitably asked is not how many nights are you staying, but how many weeks. 

The quintessential Hawaiian island that seems to draw a bit of magic from the other seven islands in the state — luxury, authentic culture, incredible restaurants, plus jaw-dropping nature and a bit of glamour —  makes for a perfect playground to settle in for an extended vacation.

The island can accommodate all types of travel. It’s perfect for honeymooners, family vacations or wild getaways with friends. Maui is the place to stay awhile and enjoy the innumerable experiences on the island and even better, become a regular.  

The perfect complement to these long Maui visits are the luxury residences with five-star hotel amenities that are scattered across the island.

Whether it is a five-star hotel that feels like your own comfortable beach house or an oasis of chic island villas that come with the “lift no fingers” type of hotel services that make a vacation a true getaway, the combination of the two is rare, but a game-changer for a luxurious, long Maui stay.

Whether you buy your own place or just rent, while staying in these residence-style accommodations you get the best of both worlds.


  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October
  • Cotton Club Deck - October

The Wailea Beach Villas and the Montage Kapalua Bay are two of these resorts naming the game in the luxury, amenity-filled residences realm on the island. Both offer up to four bedroom residences with stunning views of the Maui coastline, while charming guests with their extravagant hospitality.  

Daily maid service, spas, grocery service, concierge, bellman, car services, beach and pool attendants — you name it, the spacious villas and penthouses will make you feel at home.

Wailea Beach Villas

The Wailea Beach Villas, tucked away in a prime spot along the famed Wailea Costal Walk, amidst a neighborhood of some of the best hotels and restaurants in Maui, offer penthouses and villas sizing up to 4,000-plus square feet for rent or purchase.

When you arrive in the swanky lobby of the villa resort greeted by the welcoming staff, you will forget you’re not actually at a hotel.

As guests hop on the private elevator designated for each residence, they can unwind in their serene space equipped with state-of-the-art appliances, fully stocked kitchens, wine fridges, enormous Lanais (the Hawaiian local’s way to say patio) all with postcard-level ocean views, and all possessing the comforts of your fanciest version of home. Many villas even come with private plunge pools and outdoor showers.

Adult Pool Wailea Beach Villas
The adult pool at the Wailea Beach villas.

Guests are welcomed with banana bread from a talented Hawaiian local using fresh island ingredients. This authentic greeting sets the standard for the additional local details scattered throughout the resort, including custom-created skincare products with aromatics from the island used in each villa.

When you are ready to venture out of their ultra-luxe living space, the property’s team of concierges can set up any off- property experiences and escort you there in the resort’s Tesla SUVs.

The property also recently debuted a new Bed and Breakfast package, which provides credit for a daily complimentary breakfast at Longhi’s restaurant, located right next door at The Shops at Wailea, a premier shopping and dining district on the island.

During the day of soaking up the famous local rays, the adult pool, family pool or beachfront areas offer attendant service and even a massage hut for midday relaxation.

After the sparkling Maui beaches are fully embraced, the private pedestrian access along the tiki-lit Wailea Path will lead to fun adventures to the neighboring hotels such as the Four Seasons Maui, boutiques and art galleries and star-studded restaurants such as Spago and Morimoto — just a walk away from your swanky residence.

The five-star hotel’s neighborly love has its extra perks. Get reservations at the traditional Luau or listen to the authentic island music with a wave-crashing backdrop while grilling out on your Lanai and watching the magical Maui sunset.

With the showcase residences and the top resort amenities, this is the kind of place that goes from second home to primary home.

Montage Kapalua Bay

The Montage Residences at Kapalua Bay bring 84 oceanfront luxury residences. These dream homes sit perched on a 22,000-acre enclave surrounded by nature preserves along the western shore of Maui and make the perfect place to call home for a long relaxing vacation.

Even if you’re just coming to the property as a hotel guest, you are welcomed into a spacious abode-like suite with a fully stocked kitchen and living room flowing seamlessly to a gigantic private Lanai to live the life of a true vacation homeowner.

Residence owners and hotel guests are treated with unscripted and gracious service. Even at full capacity, the property never feels crowded, and the hotel employees will recognize you by name as if you’re a local.

Each night at turndown service, guests are presented with the evening news and resort offerings including packed wellness and activities menus.

MKB-Architectural-Cane _ Canoe-Patio-Day
Cane and Canoe, The Montage’s signature dining destination is the perfect mix of authentic island luxury.

The property’s endless happenings — the Montage’s signature spa and wellness facility, two championship level golf courses, four restaurants, multi-tiered pools for both adults and families, five white sand beaches brimming with sea turtles for world class snorkeling and miles of hiking trails — will keep you busy in between all the relaxing at your residence.

The exceptional 30,000 square feet of spa wellness facilities harness the essence of Hawaii with a palette of spa therapies and beauty treatments inspired by the ancient history and tropical surroundings.

Walking down a fragrant garden path to a massage made to mimic the relaxing tempo of the waves of the ocean in a private open-air suite brings a whole new meaning to immersive relaxation.

The Montage Kapalua Bay brings the best of island culture with partners like Veuve Clicquot bringing weekly cocktail soirees at the aptly dubbed Champagne Hale in the charming Cliff House overlooking the ocean.

You’ve never seen a sunset until you’ve watched one from the Maui cliffside while sipping on a delectable champagne cocktail. The locals cliff jumping off the rocks make for super authentic and jovial entertainment.

The property’s cultural center captivates guests with the real Hawaiian experience thanks to Cultural Ambassador Silla Kaina at the helm. Silla works with guests each and every day to teach them about the deep seeded Hawaiian culture that shapes the island.

The natural and spiritual priority of connecting with the land and its past become clear in an afternoon spent making leis, learning the Hawaiian language or any of other unique experiences tailored for guests to feel a part of this magical place.

Become a Local

For those wanting to purchase their own piece of luxury resort living, both properties have coveted units on the market.

The Montage Residences recently unveiled a limited collection of three-bedroom, fully furnished 2000-plus square foot oceanfront residences for sale, ranging from $2.7 to $3.8 million. The completely turnkey residences and fully serviced amenities remain a crucial combination for discerning luxury real estate buyers.

Of course residents can double down on their investment and put their condos in the rental pool for lucky vacationers, too. The Wailea Beach Villas offer two- and four-bedroom villas for rent for around $1,500 a night with all the comforts of home plus the luxuries of a fancy hotel stay. At the Montage, one of the fifth floor grand residences with vaulted ceilings and prime oceanfront views would run about $15,000 a week during peak season.

Eloise at the Plaza has nothing on these vacationers and their luxury Hawaii living.

Featured Properties


Like PaperCity Dallas on Facebook

Beyond the magazine. Get more of Dallas’ top restaurant, real estate, society, fashion and art in your news feed.