Big Island Stays Blog

Should You Rent Out Your Hawaii Property? One of the biggest questions buyers ask when purchasing a property in Hawaii is: Should I rent it out? For many, the dream is to own a second home in paradise while also earning income when they’re not here. But the answer isn’t always straightforward—especially when it comes to short-term vacation rentals. The Demand for Short-Term Vacation Rentals Nearly every buyer we work...

From May 2025 video Why Real Estate Appreciation on Hawaii’s Big Island Stands Out If you’re dreaming of investing in paradise, the Big Island of Hawai‘i might be calling your name — and not just for its views. Unlike many parts of the mainland where real estate appreciates slowly over time, the Big Island is one of those rare markets where appreciation can happen quickly and significantly. Think of places...

By Dan Polimino – KW Big Island & The Hawaii Team If you’re thinking about buying a vacation property in Hawaii and turning it into a short-term rental, the most important question you can ask is: Will it cash flow? As a self-proclaimed data geek, I believe numbers tell the real story—and I use them to help buyers make informed decisions. Here’s how we do that at The Hawaii Team....

When people think about buying a short-term vacation rental here on the Big Island of Hawaii, they always want to know one thing: “Dan, will it cash flow?” But how will you know—and will you have the right real estate professional to guide you? Over the years, I’ve said this many times: rarely do short-term vacation rentals cash flow here on the island. That’s mostly due to the high purchase...

video from July 2024 By Dan Polimino, KW Big Island | The Hawai‘i Team One of the most common questions I get is: “Dan, what are the best islands in Hawai‘i to buy a short-term vacation rental?” Let’s break it down. First, What to Avoid Right Now Let’s start with where I’d recommend not buying at the moment: Maui. As much as I love every part of Hawai‘i, the situation...

Exploring the Hybrid Rental Model in Hawai‘iBy Dan Polimino, Keller Williams Big Island | The Hawai‘i Team Here are the three common ownership models people explore here in Hawaii: 1. Traditional Second Home You buy a home simply to use as a second residence. When you’re not on the island, the property stays vacant. Simple, straightforward—but not income-producing. 2. Short-Term Vacation Rental (STVR) This is the most popular model buyers...

To Rent or Not to Rent in Hawai‘i: Understanding Your OptionsBy Dan Polimino, Keller Williams Big Island | The Hawai‘i Team Today, we’re talking about a big question many buyers have: Should you rent out your property in Hawai‘i, or not? And what about a third option—a hybrid model like a 30-day-plus rental? Nearly every buyer who contacts us at The Hawai‘i Team is interested in a short-term vacation rental....

Short-Term Vacation Rentals in Hawai‘i: What You Need to Know Today, I’m diving into one of the most frequently asked questions we get—by far the number one question we hear from clients: “Tell me about short-term vacation rentals.” Everyone wants to know the rules. Where can you do them? Where can’t you? How much money can you make? This post is meant to give you a foundational understanding of how...

What’s the ROI on a Short-Term Vacation Rental in Hawaiʻi? Hi, I’m Dan Polimino with Keller Williams Big Island and The Hawai‘i Team. Today, I’m sharing part three of our series on short-term vacation rentals. If you missed parts one and two, you can find them on our YouTube channel. Part one covers what homes or condos qualify for short-term vacation rentals. Part two discusses how to manage one of...

Short-Term Vacation Rentals in Hawaii: What You Need to Know (Part 1) By Dan Polimino, The Hawaii Team at Keller Williams Realty, Big Island Today, we’re kicking off a three-part series on short-term vacation rentals. This is a huge topic. Nearly every buyer who calls us at The Hawaii Team asks about short-term vacation rentals—specifically, whether they can rent out a property they purchase. Because the topic is so extensive,...