All Things Maui Real Estate - Discover Maui With Evan

Buying a Second Home on Maui: Insight, Tips, Do's and Don'ts

The Complete Guide to Buying a Second Home on Maui

Buying a second home on Maui can be one of the most exciting and life-changing decisions a person can make. I've worked with a lot of second-home buyers over the years, and what I've found is that most of them have been thinking about this for a long time.

Maybe they started coming to Maui as kids, and as adults, they want to share that with their children. Maybe they fell in love with the island on a honeymoon and have always felt a connection. Maybe they've been renting for longer periods each year and have finally decided it makes more sense to own than to keep renting.

Whatever has you thinking about buying a second home on Maui, I want to share my experience and help you navigate this…

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What Bill 88 Means for Kihei Condo Buyers and Sellers

What Bill 88 Means for Kihei Condo Buyers and Sellers

If you own a condo in Kihei, or you've been thinking about buying one and have been waiting on the sidelines while the Bill 9 situation played out, here is an update on how things are developing.

On June 19, 2026, the Maui County Council passed Bill 88 on second and final reading by a 7-2 vote. It now heads to Mayor Bissen for his signature, which is widely expected, given that he authored Bill 9 and testified in support of Bill 88 himself earlier this spring.

Once signed, it becomes law. This is a big deal for anyone with a stake in the Kihei condo market, as owners in several complexes are likely to be able to put this stress behind them while others will be looking to either appeal for…

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Upcountry Maui Real Estate Guide: Living in Kula, Makawao & Haiku

Upcountry Maui Real Estate: Your Guide to Kula, Makawao & Haiku

When most people think about buying real estate on Maui, their minds immediately jump to the ocean. They imagine beachfront condos in Kihei, luxury estates in Wailea, or resort living in Ka'anapali. And I get it. The coast is spectacular. But after 16 years of living and working on this island, I can tell you that some of the most unique, sought-after, and frankly underappreciated real estate on Maui is found somewhere else entirely — higher on the slopes of Haleakala.

Upcountry Maui is a world unto itself. The moment you start climbing Haleakalā Highway and the temperature drops a few degrees, the air gets a little crisp, and the landscape shifts from dry coastal scrub to lush…

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Short Term Rental Rules on Maui in 2026

A Guide For Maui's Short-Term Rental Rules in 2026

As a realtor on Maui who has helped buyers and sellers of short-term rental condos for years across many complexes on the island, I have developed a guide to help anyone navigate Maui County's rules on short-term rentals. 

In this guide, I’m going to discuss why Maui is such a popular choice for a location for investing in short-term rental condos (STR), all of the things you need to know about owning and operating an STR on Maui, and how the rules for short-term rentals govern owning and operating your investment here. 

You may be aware that Maui County is currently in the middle of efforts to pass a proposal from the Mayor to ban short-term rental rights for around 7,000 condo units across…

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Best Interior Designers on Maui: Transform Your Island Home or Condo

Choosing the Best Interior Designer on Maui

Transforming your space with the perfect interior design is easier said than done. Maui is a location unlike any other, and there are some unique challenges to successfully designing or redesigning your living space. Great designers will embrace the laid-back vibe of island life while balancing your taste, needs, and budget. 

Many of the newer condos and homes on Maui feature open floor plans and ample indoor-outdoor living spaces, while older properties may lack a contemporary layout and require more remodeling.

Either way, a great interior designer will usually strive to incorporate a tropical aesthetic with materials that withstand the area’s salty air and intense UV rays.

The best interior…

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Top 13 Vacation Rentals on Maui to Rent or Own

Maui's Best Vacation Rentals to Rent or Own

From Maui’s incredible beauty and world-class beaches to its unforgettable sunsets and breathtaking scenery, it is the ultimate destination for a tropical island getaway.

When searching for a vacation rental on Maui, either to rent or to own, most people are looking for something that combines the comforts and luxuries of home with the authentic feel of the islands.  However, with numerous vacation rentals on Maui to choose from, identifying the property that’s the best fit for you can be a little overwhelming.

After 16 years of living and working on Maui, with intimate knowledge of these complexes, I’ve put together a short list of some of the best options Maui has to offer at a variety of price…

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Wailea Real Estate Market Report April 2026

Wailea Real Estate Market Report April 2026

Wailea is one of Maui's most pristine and coveted resort areas. Known primarily for its amazing sunny weather, calm beaches, and luxury lifestyle, Wailea is also home to some of Maui's most beautiful properties and a robust luxury real estate market.

There are 18 different communities with condos for sale in Wailea, 9 of which are currently approved for short-term rentals and 9 of which are not. There are 8 residential neighborhoods with homes for sale in Wailea, all of which are gated. 

Makena, a smaller but more expensive market, is included in MLS statistical reporting alongside Wailea. However, with the addition of Makena Golf and Beach Club and the ultra-luxury oceanfront homes in Makena, the…

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Does Maui Have a Water Problem?

Does Maui Have a Water Problem? 

The Hawaiian Islands occupy a unique position on Planet Earth and are subject to distinct, sometimes extreme, weather patterns. Here in the middle of the Pacific Ocean, 2,300 miles from California, Hawaii exists because of a fixed volcanic hot spot in the ocean (a deep plume of magma under the slowly moving Pacific Plate) that has been flowing for millions of years and is currently creating the Big Island.

It's a miracle that life exists in Hawaii and living here in Hawaii, at least in my humble opinion, is also miraculous.

Amazingly, Hawaii Island, the largest of the chain, is still growing from its active volcanoes, while the rest of the main Hawaiian Islands, Maui, Oahu, Kauai, Lanai, Molokai, and Niihau,…

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Montage Kapalua To Become St. Regis Under Marriott Management

Montage at Kapalua to Become St. Regis 

It was recently announced that Marriott International signed a management agreement with the Tennessee-based owners of the Montage Resort at Kapalua Bay, KWC Management.

The former management agreement was between KWC Management and White Label Asset Management, who continued to operate under the Montage brand after KWC had purchased the property in November of 2023. Marriott will now operate the Resort under their luxury St. Regis Resort Division. 

The Montage Kapalua property has consistently been regarded as one of the very best resorts in the State of Hawaii, and last traded hands when Lantern Asset Management purchased it in 2013 through a foreclosure sale, after it was owned by the infamous Lehman…

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HOA Fees on Maui : Explained

HOA Fees on Maui: Explained

Homeowners’ Associations have been around in the United States since the mid-20th century. They operate as non-profit organizations whose primary objectives are to organize, maintain, and protect properties along with their owners within planned communities or subdivisions, condominium complexes, and cooperative ownership agreements. There is a wide variety of HOAs across the country, and specifically on Maui. 

Some HOAs can be very small, with only a few properties in the association, while others can involve 1,000s of homeowners. The most common type of HOA on Maui is a condominium community HOA.

There are hundreds of condo complexes on Maui, and their HOAs use the funds they collect from owners to cover things…

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