Big Island Memory Making

Timing Is Everything...

What weeks are the least and most expensive to visit the big island?

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Big Island Memory Making
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Eddie Yoon
Sep 08, 2025
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Credit: Michela Buttignol/Travel+Leisure

Aloha,

A vacation in Hawaii is not cheap. But timing is everything. If you have flexibility, there are times of the year that are meaningfully cheaper. The least expensive week is 37% cheaper, whereas the most expensive week is more than double the average price.

Low Season vs. High Season


We scrape prices for 120 single family home VRBOs in the Waikoloa, Mauna Lani and Mauna Kea region of the big island. This gives us a robust database of pricing across a wide array of VRBOs at a week by week level. To simplify things, we normalized all the data on a per bedroom basis.

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A guest post by
Eddie Yoon
Co founder of Category Pirates Founder of EddieWouldGrow, LLC Co-founder of Big Island Memory Making Author of Superconsumers & 60+ HBR articles
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