Hostess With The Mostest: Homes With The Best Guesthouses

Posted by Staff Writer on Thursday, March 18th, 2021 at 11:49am

Here on Maui, aloha is at the core of everything in our daily lives. From waving at a friendly face on the street to letting someone go ahead of you in traffic, to helping your neighbor with their groceries. It’s no wonder that at any home on Maui, you’re likely to see friends and family gathering for no reason other than to “talk story” or hangout. 

What better way to accommodate Maui’s favorite pastime than gathering a list of homes with the best guesthouses!

A guesthouse is our favorite (and most stylish) way to host visiting guests. It’s both an extension of your home and a reflection of your hosting personality, whether it be clean towels, a signature welcome mat, or a mural of your favorite beach. Guests should feel like they are a part of the family while being able to sneak in a few relaxing moments at night in the comfort of their own space. 

We can’t think of a better way to start the summer of 2021 than having the ultimate Maui experience right in your backyard. This year, treat your guests to 2,300 square feet of living space and a private pool on the slopes of the West Maui Mountains or a luxury two-bedroom apartment with its own first-class Pilates, yoga, and dance studio (should we even mention the CrossFit room and climbing wall).  Or maybe they would prefer a private pool house overlooking the Wailuku cliffside or a completely separate home equipped with an outdoor soaking tub in the Makawao countryside. To be honest, any of these homes would leave guests breathless.

Whatever speaks to your hosting style, bring the spirit of “aloha” to everyone who graces your home right from the moment they arrive. This, paired with a weekend of hiking through the rainforest, playing in the Maui waves, and eating only the best local cuisine is enough to beat any overpriced 5-star resort.

55 N. Lauhoe Place Launiupoko, Hawaii

4725 Hana Highway Haiku, Hawaii

4933 Kahekili Hwy Wailuku, Hawaii

810 Piiholo Road Makawao, Hawaii

37 Lower Ulumalu Road Haiku, Hawaii





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