Each island is its own market and its own regulator. Oahu concentrates legal rentals in the Waikiki and Ko Olina resort zones; Maui’s resort districts carry its volume; the Big Island runs from Kona and the Kohala coast; and Kauai’s legal inventory sits in designated visitor areas. Values are high, rebuild costs are higher, and legal supply is deliberately scarce.
Ocean, lava, wind, and fireHawaii stacks perils most states never see together: hurricane and tropical-storm wind, coastal flood and surge, volcanic and lava-zone exposure on the Big Island that many carriers surcharge or decline, and, since Lahaina in 2023, wildfire treated as a first-order underwriting question. Standard policies exclude flood everywhere and treat catastrophe deductibles as percentages.
Hawaii claims most often fail on zone and status: an unpermitted or wrongly zoned rental gives a carrier an opening, lava-zone exclusions surprise Big Island owners, and hurricane deductibles land in the tens of thousands on high-value homes. Confirm the property’s legal rental status first, then your hurricane deductible in dollars, your flood coverage, and any lava-zone terms.
State law now lets the counties phase short-term rentals out entirely, and each county uses its authority differently. Oahu confines rentals to resort zones with registration and steep fines for illegal operation. Maui is phasing out roughly 7,000 apartment-zoned rentals on a 2029 to 2031 timeline, with litigation pending. The Big Island’s Bill 47, in effect since July 1, 2026, requires every rental to register with the county at $250 to $500 a year, with fines to $10,000 for operating unregistered. Kauai’s visitor-district model has been closed to new residential permits since 2008. Statewide, every operator carries GET and TAT licenses, displayed on listings, with combined taxes in the high teens. Verify the island, the zone, and the permit before anything else.