Kona Investment Property
Maile Woodhall (pronounced Miley) is a Kona born Realtor who helps investors buy vacation rentals, condos, homes, and land in Kona and across West Hawaiʻi. Many of her investment buyers live on the mainland or overseas. This page covers what to check before you buy. It is general information, not tax, legal, or investment advice.
Vacation Rentals in Kona
Two things must be true before a Kona property can be rented for less than 30 days. Hawaiʻi County must allow it, and the condo association must allow it.
The County allows short term vacation rentals mainly in resort zones and certain commercial zones. Outside those areas, a property needs a Nonconforming Use Certificate that was issued when the County rules began.
Since September 1, 2026, the County requires every rental of less than 180 days to be registered. A registration ends 90 days after a sale, so a new owner who plans to rent must register again. Registration needs a General Excise Tax license, Transient Accommodations Tax registration, and current property taxes.
Rules can change. Confirm the current status with the County of Hawaiʻi Planning Department before you count on rental income.
Kona Condos and Long Term Rentals
Each condo association sets its own rules. Some allow vacation rentals. Others require stays of 30 days or more. Before you make an offer, Maile looks at the monthly fee, the reserves, the rental rules, insurance, and whether the land is fee simple or leasehold. Some lenders also need to approve the condo building itself.
Where vacation rentals are not allowed, a long term rental can still work. Some investors like the steadier income and lower wear. Gather real fees, taxes, insurance, and management costs, and compare what similar units have earned.
Buying From the Mainland or Overseas
Maile can walk a property on video, gather the records, and handle the steps that need someone in Kona. Many owners hire a local property manager for bookings, cleaning, and taxes.
Plan for the sale too. When an owner who lives outside Hawaiʻi sells, State law (HARPTA) has escrow withhold 7.25 percent of the sale price, unless an exemption applies. Sellers who are not U.S. persons can also face a 15 percent federal withholding (FIRPTA). Ask a tax professional how these apply to you.
Buying a working farm instead? See Buying a Working Farm in Hawaiʻi.
1031 Exchange Basics
A 1031 exchange is a federal tax rule. It can let an investor sell an investment property and buy another one while putting off capital gains tax. Under IRS rules, you name the new property within 45 days of the sale and close within 180 days. A qualified intermediary holds the money in between. A home you live in does not qualify.
Hawaiʻi has its own forms for exchanges, and HARPTA withholding can still apply. Talk with your tax advisor and your escrow company before you list or make an offer.
Ready to look at Kona investment property? Call or text (808) 482-5800. Maile helps buyers and sellers in Kona, on every Hawaiian island, and on the mainland and overseas through eXp Realty.
Maile Woodhall, REALTOR, RS-88019. The Agency Team Hawaii, brokered by eXp Realty, RB-21841.