Performance indicators for the Kailua short-term rental market based on reliable data.
Listings
Reliable / Active
Cap Rate
Middle-Earners Gross Yield
Revenue
Middle-Earners Revenue
Occupancy
Middle-Earners Occupancy
Home Value
Median Home Sale Price
Top Earners
Top-Earners Revenue
The highest-performing listings in Kailua.
Loading top listings...
Challenging to Investors
New STRs are practically limited to resort zones, with stringent caps (two rooms/occupants per bedroom) and high compliance burden (e.g., $1,000 registration + $1M liability insurance). The Department of Planning and Permitting actively enforces under a 30‑day minimum, penalizing illegal operations up to $10,000/day, creating substantial investor risk.
Local STR Agent
STR specialist · Kailua, HI
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.