Get all of the information you need to make an informed decision about buying or selling real estate on Maui. 

The Complete Guide to Buying a Second Home on Maui

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

Maui Short Term Rental Rules

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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Maui's Best Vacation Rentals to Rent or Own

Vacation Rentals Maui

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

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

1031 Exchange Maui

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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HOA Fees on Maui: Explained

Why are HOA Fees on Maui So Expensive?

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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Explore Maui Neighborhoods and Communities for Families

Neighborhoods on Maui for Families

For a relatively small island, Maui offers a large diversity of lifestyles and microclimates that appeal to a wide range of people.

If you would like a hot, sunny, and dry climate with a beach lifestyle, you’ll find yourself drawn to Kihei, Wailea, Lahaina, or Ka’anapali.

Windsports and surfing enthusiasts are typically drawn to the windswept Northshore, where the community of Spreckelsville offers unparalleled access to extreme ocean sports and the Maui Country Club. Others are seeking a cooler, more rural, tropical rainforest setting in places like Makawao, Haiku, and Hana. Or even a relatively cold setting in upper Kula.

As you search for the ideal community for you and your…

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The 10 Best Luxury Residential Condo Communities on Maui

 Maui's Best Luxury Condo Communties

While much of the focus on Maui’s condo communities over the last two years has centered on short-term rental complexes and which ones are possibly affected by Bill 9, many buyers still prefer condos for personal use only, as primary residences or second homes. 

There are many benefits of using a condo zoned for long-term use only if your plans are to live in it full-time or spend more than just a few weeks in the unit per year. The first benefit is significant savings on property tax rates. 

Short-term rental condo owners pay a much higher property tax rate, approximately double that of the non-owner-occupied rate. If you're purchasing the unit as your primary residence, you’ll pay an…

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Coldwell Banker Global Luxury Real Estate Market in Review 2025

Coldwell Banker Global Luxury Market Report

Every January, Coldwell Banker Global Luxury provides a year-in-review report for the global luxury real estate market. It is a wealth of information that provides in-depth analysis, supported by data, helping add context and color to what we are seeing here on Maui in our own luxury market. 

While the general Maui real estate market has been down due to a variety of factors (bill 9, interest rates, rising insurance premiums, etc) the luxury market showed resilience while navigating the current set of geopolitical and economic factors and was able to preserve values better during this market cool-down period.

The Trend Report, as it is called, is a fairly long read and, I must…

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The Best Golf Course Homes and Neighborhoods on Maui — and What They’re Asking

Best Golf Course Real Estate Maui

I should start by saying that I’m writing this from the perspective of a true golf lover. Taught to play by my grandfather, I’ve been playing since I was about 7. Admittedly, I should score better than I do for having played for over 35 years now, I just love the game.  One of the reasons I moved to Maui back in 2010 was to be able to play golf in near-perfect weather 12 months a year. 

I’ve played all of the golf courses on Maui.  Many of them I’ve played dozens, if not hundreds, of times. Safe to say, I’m a fan. 

I also know a few things about real estate and golf course homes on Maui. I actually live on a golf course myself. So, this isn’t some generic AI…

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