Who’s Actually Doing STRs in Waikiki Right Now?

Question

Based in Southern California and looking to break into the Waikiki short-term rental market and connect with someone experienced in this space.

My goal is to purchase an STR in Waikiki, primarily for the tax advantages and long-term appreciation, while also generating consistent cash flow. I understand this market is highly regulated and not all condos or zones allow short-term rentals, so I want to make sure I’m approaching this the right way from day one.

From what I’ve gathered, STRs are generally only permitted in resort-zoned areas or specific buildings with the proper approvals (or existing nonconforming use certificates), and navigating that correctly seems to be the biggest factor in making a good investment here.

I’m looking for:

• Guidance on identifying truly STR-eligible properties (not just “Airbnb-friendly” listings)• Insight into current regulations, zoning, and compliance requirements• A potential mentor

If you’ve invested in Waikiki or Oahu STRs and are open to sharing insight—or even just pointing me in the right direction—I’d really appreciate connecting.

Andrew Steffens · Answer

@Bryan Vukelich for all things Hawaii!

Bryan Vukelich · Answer

Aloha Samantha and as always, big mahalo @Andrew Steffens for the recommendation.

Samantha, I specialize in helping investors acquire STRs on O'ahu - many of them doing it for the tax advantages. I'll email you some information and you're welcome to contact me at any time - I'm here to serve way I can.

Jacob D Adamczak · Answer

@Samantha Zanotelli

Waikiki can be a great market, but you’re right that eligibility/regulations are the first hurdle and can make or break the deal. Once you narrow down properties, the underwriting side becomes huge too — projected STR revenue often gets overestimated or incorrect comps are used.

My team works on revenue management/pricing (not brokerage or zoning), but happy to run a free revenue estimate on any property you’re considering that passes the regulation check so you can pressure test the numbers. Feel free to DM me if helpful.

Duc Ong · Answer

@Samantha Zanotelli

Samantha, you’re asking all the right questions for Waikiki. This market rewards people who treat it as a zoning and underwriting puzzle first, and an Airbnb dream second.

Focus only on properties that clearly fall into one of the official “legal STR” buckets: resort‑mixed use / hotel‑type buildings, carved‑out Bill 41 buildings, or units with an active NUC. If it doesn’t fit one of those, assume it’s not a true STR, no matter what the listing says.

For anything you like, verify three things before getting attached: zoning on the tax map, condo docs/house rules, and either STR registration or NUC status through the city, not just from the MLS remarks.

Underwrite two stacks for every deal: legal STR numbers and a “worst‑case” 90‑day or long‑term rent. If the LTR side won’t cover debt service, you’re one ordinance away from a problem.

With TAT/GET, registration fees, and higher operating costs, you want to be conservative on occupancy and nightly rates instead of just copying AirDNA top‑line.

You already have the right thesis of tax advantages + long‑term appreciation, so it really comes down to picking the right building and not overpaying for “illegal yield.” If you want to sanity‑check a couple specific Waikiki buildings or listings, I’m happy to walk through how I’d pressure‑test them the same way I do for my own Oahu clients.

Leah Walczak · Answer

Samantha — love that you're approaching this deliberately from day one. Waikiki is one of the markets where the LTR pressure-test matters most, because the zoning restrictions that let your property operate as STR can also vanish. The question I'd make central to your underwriting: if you lose STR legality on this unit, does the LTR rent cover your debt service? If yes, you have real downside protection — you can hold. If no, you're exposed to a single regulatory change. Most Waikiki condos pencil a 20-30% gap between STR net and LTR net, but the LTR number is what determines your worst case.

Julie Bea · Answer

Welcome to the Waikiki madness, Samantha! It’s a goldmine but definitely a minefield with the 90-day rule. If you aren't in a Resort zoned building like the Ilikai or Waikiki Shore, you’re basically stuck with 3 month minimum stays, which usually doesn't hit those cash flow goals you're after.

Also, don't forget the hidden costs Hawaii just bumped the TAT tax to 11% this year, so your margins need to be tight from day one. I've spent a lot of time vetting buildings here that are actually legal for daily rentals so you don't get hit with those fines.

Mike Grudzien · Answer

This is a national forum. Have you thought of reaching out and networking locally (Facebook groups, REIA groups) in the specific local market that you are trying to understand?

Who’s Actually Doing STRs in Waikiki Right Now?

Who’s Actually Doing STRs in Waikiki Right Now?

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