Let’s start with the not-so-sexy stuff.

First is income, in other words, your ability to rent the unit when you are not staying on the island. Rental income is important because it helps you defray the costs of owning the property, and even helps you qualify for a mortgage if you are not paying cash.

You may have heard of the Minatoya List, which is Maui County’s list of condos allowed to offer vacation-rentals in Apartment-Zoned complexes. Being on the list used to mean you were safe. But these days? Not so much. 

With ongoing housing shortages and potential regulatory changes, even Minatoya List properties could lose their ability to do short-term rentals if Maui County decides to tighten the rules, which looks to be likely.

That uncertainty has a lot of owners sweating right now, and it’s why we recommend that anyone who needs rental-income purchase only in a Hotel-Zoned complex, which is approved for short-term use.

Outside of zoning issues, there are also insurance spikes. Thanks to a combo of wildfires, rising construction costs, and changes in weather patterns, insurance today costs more than it did a couple of years ago. That plus higher property maintenance costs leads to increased HOA fees.

And let’s talk about the buildings themselves. Many Maui condos were built back in the 70s and 80s, which often means deferred maintenance. There are roofs that need to be replaced, plumbing that needs to be upgraded, parking lots that need to be repaved, and buildings that need to be repainted, all contributing to increased costs, and sometimes leading to special assessments. 

Oh, and don’t forget potentially lower visitor counts since the Lahaina fires. With more vacation rental options on the market and fewer tourists, some lower end units are sitting empty longer than their owners would like.

I don’t mean to burst your bubble, but I’d rather you know the truth before we get into escrow and you learn the facts. 🙂

The bottom line is that if you’re thinking a Maui vacation rental is going to be your golden goose, you might want to reconsider. When you factor in all the costs, maintenance, and fluctuating rental income, your actual cash-on-cash return might not even beat a boring old index fund.

With all that said, if you worry that you missed the boat, you may be looking at the wrong end of the equation because…

Okay, now let’s flip the script and talk about why people are still buying vacation rentals — because there is a lot more to the story than dollars and cents.

That condo on Maui? It’s not just an asset. It’s your front-row seat to humpback whales breaching at sunrise. It’s where your kids learn how to surf. Where you sip wine on the lanai and watch the sky turn pink and gold while holding the hand of someone you love. 

It’s memories in the making, year after year, with the people you care about most.

Some of my earliest, happiest memories are of family trips to Maui, playing in the waves, sandy towels draped over beach chairs, the smell of salt air mixing with sunscreen as we headed off to explore some new restaurant or attend a Luau. 

Those vacations were more than just time off, they were the foundation of my lifelong love for this island. And in 2001, when I had the chance to move here and build a life on Maui, those memories were a big part of why I said yes.

Now, when walking down the beach with family and friends, I’m reminded this isn’t just about real estate. It’s about building a legacy, and creating new traditions with people you love. 

It’s about giving your family the same gift my parents gave me: Time together in paradise, making memories that last long after the sun has set.