In October, the weather in Kailua-Kona is typically warm. Average daily high temperature in October is about 24 degrees above zero. On average, Kailua-Kona has 28 rainy, 2 sunny, and 1 partly cloudy day in October. The rains are usually heavy. October as well as January, February, March, and April is considered the most uncomfortable time to visit Kailua-Kona.