Two Rare Kona Homes You Can Legally Rent on Airbnb

As the Big Island real estate market shifts and inventory grows, we’re entering a more balanced-if not buyer-friendly—market. With over 149 homes currently for sale in Kailua-Kona alone, unique investment opportunities are emerging. One of the rarest? Single-family homes with active short-term vacation rental permits and properties in a resort-zoned area.

I’m often asked: “Can I run a short-term rental in a single-family home?” The answer isn’t simple. The County of Hawaii continues to adjust and tighten regulations on vacation rentals, especially those in residential zones.

Suppose you’re considering owning a single-family home and running it as a business on Airbnb or VRBO. In that case, your best bet is to purchase a property within a Resort node or one that has an existing non-conforming use permit (NUP).

🔑 As of today, only one homes in Kailua-Kona hold an active non-conforming use short-term rental permit, and only three are for sale in a resort-zoned area of Kailua-Kona. As you can tell, they are rare, valuable, and can offer significant income potential.

In this post, I’ll highlight two of these rare properties, located in resort-zoned areas of Kona. Whether you’re looking for your dream investment, a second home with income potential, or a retirement plan with flexibility, these homes offer a smart way to purchase a home in today’s evolving market.

Let’s take a closer look at each of these rare opportunities in Kailua-Kona…

75-5952  Alii Dr, Kailua-Kona, HI 96740 | MLS 720834 | Listed by Mike Despard & Kristi Despard, Real Broker LLC

Located in resort zoning, this active STVR (short-term vacation rental) on Alii Drive is your opportunity to own an oceanfront property that you can rent short-term, long-term, or enjoy for yourself. Built in 2011, it’s one of the newest oceanfront homes on Kailua Kona’s scenic road that connects Kailua and Keauhou.

The three-story structure features a 1,332 SF carport on the bottom level, 3 bedrooms & 2 bathrooms (& laundry room) on the middle level, and the living area with kitchen/dining, office, and half-bath on the top level. All levels are connected with an elevator. The home also features two expansive, oceanfront lanais. Enjoy breathtaking sunsets and dolphins & whales splashing in the ocean.

This property is located within a resort zone in Kailua-Kona, where the zoning permits short-term vacation rentals. Like other properties in designated resort areas across the island, zoning in these locations is highly stable.

Discover more about this short-term rental property located at 75-5952 Alii Drive.

78-111-A Holua Rd, Kailua-Kona, HI 96740 | MLS 720834 | Listed by Daniel Polimino & Bruce W. Kekuewa, KW Big Island 

Perched atop a scenic bluff overlooking the sparkling waters of He‘eia Bay, “Kinohi at He‘eia” is a rare gem nestled in the heart of the historic Keauhou Resort region. This expansive two-story retreat offers five bedrooms, three baths, and a separate studio guest house, comfortably accommodating up to 14 guests, making it the ideal island getaway.

The home has a transferable short term vacation rental registration. Set on a lush half-acre, the property is graced with tropical landscaping, including ulu (breadfruit) and Samoan coconut trees, and features, a spacious lawn perfect for volleyball, lawn games, gazebo or simply relaxing by the magnificent pool and the double hammock as you watch surfers and, in season, migrating whales offshore.

This property is located within a resort zone in Kailua-Kona, where the zoning permits short-term vacation rentals. Like other properties in designated resort areas across the island, zoning in these locations is highly stable.

Learn more about this beautiful short-term rental property located moments away from the ocean – 78-111-A Holua Road.

Final Thoughts

In a shifting market where regulations are tightening and inventory is growing, finding a legally permitted short-term rental home in Kailua-Kona is more than just a potential investment—it’s a rare opportunity. Whether you’re looking to generate income, secure a flexible second home, or build long-term value in Hawaii real estate, these properties offer a unique way to own a single-family home with built-in rental income

If you’re curious about short-term rental opportunities or want to tour one of these rare homes in person, I’d be happy to guide you through the process. Let’s connect—your dream investment might be closer than you think.

With Aloha,
Leeana