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Kailua, HI
Challenging To Investors
Local STR Agent

Short-term rentals are strictly limited in Kailua, Hawaii. Kailua operates under the City and County of Honolulu's short-term rental regulations, which permit STRs only in resort-zoned areas and a few specific apartment-zoned locations. Outside these designated zones, short-term rentals (rentals under 30 consecutive days) are prohibited, with very limited exceptions for grandfathered properties operating prior to October 22, 1986.
The legal framework is enforced by the Honolulu Department of Planning and Permitting (DPP), and while recent legislative changes have created some enforcement confusion regarding 30-day vs. 90-day minimums, the practical reality is that non-resort zoned areas, including most of Kailua, do not permit new short-term rental operations.
Starting a legal STR business in Kailua requires careful navigation of restrictive zoning laws and a multi-step compliance process:
Bed and Breakfast Homes (B&Bs)
Transient Vacation Units (TVUs)
Honolulu Department of Planning and Permitting
Key Staff Contacts:
Office Hours: Monday-Friday, 7:45 AM - 4:30 PM
Email: Contact through official DPP website contact forms
Important Disclaimer: The legal landscape for short-term rentals in Kailua and across Oahu remains complex and evolving. Given the extremely restrictive zoning requirements and recent legislative changes, most residential properties in Kailua are not eligible for short-term rental operations. Investors and property owners should consult with local real estate attorneys and the Honolulu Department of Planning and Permitting before proceeding with any STR-related investments or operations.
Enforcement Note: The Department of Planning and Permitting continues to enforce STR regulations as "less than 30 consecutive days across the board," with active citations and penalties for illegal operations ranging from $1,000 to $10,000 per day.



Kailua (Hawaiian pronunciation: [kɐjˈluwə]) is a census-designated place (CDP) in Honolulu County, Hawaii, United States. It lies in the Koʻolaupoko District of the island of Oʻahu on the windward coast at Kailua Bay. It is in the judicial district and the ahupua'a named Ko'olaupoko. It is 12 miles (19 km) northeast of Honolulu – over Nu‘uanu Pali. In the Hawaiian language Kailua means "two seas" or "two currents", a contraction of the words kai (meaning "sea" or "sea water") and ʻelua (meaning "two"); it is so named because of the two former fishponds in the district (Kawainui and Kaʻelepulu) or the two currents that run through Kailua Bay.Kailua is primarily a residential community, with a centralized commercial district along Kailua Road. The population was 50,000 in 1992. In 2017 census, the population had dropped to 38,000. The population was 40,514 at the 2020 census. Places of note in Kailua include Kailua Beach Park, Kaʻōhao or Lanikai Beach, Kawainui Marsh, Maunawili Falls, and Marine Corps Base Hawaii. It was home to Barack Obama’s winter White House.
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