Buying a condo in Kihei has long been a dream for people who fall in love with South Maui’s beaches, sunsets and easygoing pace. For many buyers, it is also an investment, with the hope of renting the condo to visitors when they are not using it. In 2026, that second goal needs more homework than ever. Maui County’s Bill 9 is now law, and it changes the long-term rental picture for many Kihei condos.
This guide covers what to understand before you buy, from zoning and short-term rental rules to HOA health, taxes and closing costs. It is general information, not legal or tax advice, so plan to confirm the details with a licensed real estate professional, attorney and CPA before you make an offer.
Bill 9: The Biggest Factor When Buying a Condo in Kihei
For decades, many condos in Maui’s apartment-zoned districts were allowed to operate as vacation rentals under a grandfathered framework often called the “Minatoya list.” In December 2025, Mayor Richard Bissen signed Bill 9, which phases out transient vacation rental use in apartment-zoned districts across Maui County.
Key points as reported so far:
- Timeline: The phase-out takes effect January 1, 2029 in West Maui and January 1, 2031 in the rest of Maui County, which includes Kihei.
- Scope: Roughly 6,000 apartment-zoned units countywide are affected. Hotel-zoned and resort-zoned properties are not part of this phase-out.
- Legal challenges: Lawsuits have been filed challenging the law. Outcomes and timing are uncertain, so check the current status before you buy.
What this means in practice: two condos on the same stretch of South Kihei Road can have very different futures as rentals, depending on zoning and permits. Before you fall in love with a view, find out which category the building falls into.
Questions to Ask About Any Kihei Condo
- What is the property’s zoning, and is it on the Minatoya list or in a hotel or resort district?
- Do the condo association’s bylaws and house rules allow short-term rentals, and are any changes being discussed?
- If short-term rental use ends in 2031, does the condo still make sense for you as a second home or long-term rental?
- What has the unit actually earned? Ask for rental history, not just projections.
Know the Building, Not Just the Unit
When you buy a condo, you are also buying into an association. A beautiful remodel can hide a building that needs expensive work.
- Reserve study and budget: Is the association setting aside enough for roofs, elevators, plumbing and concrete repairs?
- Special assessments: Are any planned or under discussion? Read recent board meeting minutes.
- Insurance: Condo master policy premiums in Hawaii have risen sharply in recent years. Ask how that has affected dues.
- Maintenance fees: Understand what your monthly fee covers, such as water, cable or internet, and common-area upkeep.
- Location factors: Ask about flood zone and tsunami evacuation zone status, which can affect insurance and peace of mind.
Also confirm whether the property is fee simple or leasehold. Most Kihei condos are fee simple, but leasehold properties exist in Hawaii and work very differently.
Taxes and Costs to Budget For
Maui’s property tax system uses classifications, and properties used as short-term rentals fall into a separate class taxed at significantly higher rates than owner-occupied homes. Rates are set each year by the County Council, so check current numbers when you run your budget.
If you rent to visitors, you will also owe Hawaii’s General Excise Tax and Transient Accommodations Tax, plus the Maui County TAT. When you eventually sell, Hawaii requires withholding under HARPTA for nonresident sellers, currently 7.25 percent of the gross sales price, and federal FIRPTA rules may apply to foreign sellers. These withholdings can often be adjusted or refunded at tax time, but they affect your cash at closing, so plan ahead with your CPA.
Other costs to include:
- Furnishing and setup if you plan to rent the unit
- Professional photography and listing creation
- Property management fees
- Ongoing repairs and replacements, which come faster in a salty, sunny climate
Running the Numbers Honestly
Kihei’s strengths are real. It is dry and sunny, central to the rest of Maui and close to great beaches. Winter brings strong demand thanks to whale season and the holidays. But smart buyers in 2026 run at least two scenarios:
- Scenario one: The unit can legally rent short-term through your expected hold period.
- Scenario two: Short-term rentals end, and the unit becomes a personal residence, second home or long-term rental.
If the property still works for you under scenario two, you are on much firmer ground. If it only works as a vacation rental, make sure the zoning supports that for the long run.
How Midway Vacations Realty Can Help
Midway Vacations has a licensed real estate team and a property management team under one roof, with offices in Waikiki and right in Kihei. That combination gives buyers a practical, on-the-ground view of how buildings actually perform, not just how they look in listing photos.
Through our real estate services, we can help you:
- Identify buildings and units that fit your goals and budget
- Understand the rental and regulatory picture for specific properties
- Review rental history and realistic income expectations
- Coordinate design, staging and setup through our project management and design team
- Transition smoothly into professional management after closing
You can read more about our approach in Why You Need Midway as a Partner in Your Next Realty Investment.
The Bottom Line on Buying a Condo in Kihei
Buying a condo in Kihei can still be a wonderful decision, whether it is your future retirement spot, a family getaway or a long-term investment. The key in 2026 is to go in with clear eyes: know the zoning, understand Bill 9, check the health of the association and run numbers that work even if the rules keep changing.
Thinking about buying in Kihei or Waikiki? Contact Midway Vacations Realty to schedule a no-pressure consultation in person, by phone or by video. We are happy to share what we are seeing on the ground and help you find a property that fits your plans. Mahalo!
