All Things Maui Real Estate - In-Depth Maui Short Term Rentable Condo Guides

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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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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Using a 1031 Exchange on Maui | What It Is and How It Works

Using a 1031 Exchange on Maui to Leverage Up Without Losing Your Gains to Taxes

From the stable cash flow of rental income to the exceptional growth of property value and more, Maui investment properties hold tremendous financial potential. When you sell a rental property or second home, you will ideally enjoy a handsome profit. As is the case with all types of income, Uncle Sam try to take a cut.

Depending on how much appreciation your subject property of the 1031 exchange has had, tax liabilities from selling can be substantial. So, you'll understandably want to avoid taxes, if possible, and maximize your return on your initial investment. Fortunately, you can do so legally with one of the largest wealth-building tools for real estate…

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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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The Risks of Buying Real Estate on Maui and How to Navigate Them

What Are The Risks of Buying Real Estate on Maui?

Selling real estate on Maui, or anywhere for that matter, is rarely, if ever, as glamorous as the reality TV shows like Selling Sunset or Million Dollar Listing make it look.

My day-to-day life as a Realtor looks a lot more like early morning emails with 17 open tabs on my Chrome browser, hours a day in my car driving around the island for appointments or check-ins, often making the whole circuit from Upcountry to Kapalua to Wailea and back while making calls and texts, to return home, just to send a few more emails. 

The best part of my work day is when I’m with clients, either on the phone or in person. I spend the rest of my time in front of the soft glow of my iMac, moving deals forward…

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Maui STR Ban Bill 9 Exemption List and Temporary Investigative Group Report (Proposed 10/14/25)

Maui STR Ban Bill 9 Exemption List and Temporary Investigative Group Report (Proposed 10/14/25)

On October 14th, the Temporary Investigative Group (TIG) of the Housing and Land Use Committee reported the results of their findings to the public, which included a much-welcomed determination that the bill to take away STR rights of owners on the Minatoya List should include an exemption list of 53 properties that includes many Minatoya List condo complexes and a few BnB residential properties.

Most of us in the Maui community have been hoping to see some logic and reason applied to this issue.  Aside from the economic consequences of such a possible ban, there are many reasons why simply banning short-term rentals in apartment-zoned complexes won't…

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The Best Condo Communities in Wailea Maui

The Best Condos in Wailea, Maui

Wailea is a master-planned community that is a part of the larger Wailea-Makena area in South Maui. Established in 1971 as a low-density resort community, the incomparable Wailea Resort covers over 1,500 acres and is home to world-class beaches, hotels, shopping, dining, golf, and much more.

The beaches of Wailea include Keawakapu, Mokapu, Ulua, Wailea, and Polo beaches. Nearby, you will find 54 holes of exceptional golf at the Wailea Golf Club, dozens of great restaurants, fine shopping destinations, and other fun island activities.

Many who visit Wailea regularly decide to invest in a home or condo for themselves and want to know what the best condo complexes in Wailea are. Having a condo in Wailea offers…

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Do These 10 Things To Become an AirBnB Super Host on Maui

Running a Successful AirBnB on Maui

While some visitors to Maui still prefer to stay in a hotel, more and more visitors each year are looking for a more affordable and more intimate experience on their Maui vacation by looking for AirBnB’s in smaller short term rentable communities. 

It’s no secret that Maui has a large variety of short term rentable communities, particularly in Kihei, Wailea, Ka’anapali and Kapalua, where owners utilize their units as investment properties and list for nightly rentals on AirBnb and VRBO. 

In addition to being a second home for the owners, these units produce considerable rental income and allows owners to continue building equity and working toward their financial goals. 

However, not all of these units…

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6 of the Best Kihei Condos For Sale

A Buyer's Guide To The Best Condos in Kihei

Kihei is a Hawaiian beach community on the southern shores of Maui. Kihei’s location means that it's perfectly placed for easy access to the best of what Maui has to offer, like the picture-perfect beaches of Wailea and Makena, surfing, snorkeling, ocean cruises, and more. There are so many great things to do in Kihei that many consider buying a home or condo here themselves. 

Specifically, there are considerable benefits to owning a short-term rentable condo in Kihei. Thanks to its proximity to some of Maui’s best beaches, Kihei is a popular vacation destination and therefore has a large number of condo complexes compared to other Maui communities.

The three Kamaole beaches along with Sugar Beach…

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