What just happened with Bill 9 and Maui vacation rentals? A Lot. On September 22, 2026, after roughly five hours of public testimony, the Maui Planning Commission voted 6 to 2 to recommend against hotel zoning changes for 43 of the 48 properties being considered. That represents a rejection of 90% of the buildings that […]
Tag Archives: Anthony Sayles
Wailea Ekahi vs. Wailea Ekolu – condos with similar names that offer different lifestyles
Did you know that 8 out of the 18 Wailea condo communities have names that start with the word Wailea? It’s a certainly a prestigious word with a reputation built over decades as one of the top destinations for the enjoying luxury lifestyle on Maui, so it’s not surprising that the word Wailea is used […]
Wailea Point to potentially resume short term rentals after important court decision
If you’ve been following the recent legal battle involving Wailea Point, you’ve probably asked yourself one question: What does this actually mean? Here’s the short answer… The Ninth Circuit Court of Appeals has restored Wailea Point’s previous 30 day minimum lease policy, reversing the 2022 amendment that increased the community’s minimum lease term to one […]
Maui’s Vacation Rental Battle – Why Bill 88 Matters
Over the past two years, Maui has witnessed one of the most significant policy shifts in its real estate history. Whether you agree with the direction or not, one fact is difficult to ignore: the market responded long before any ordinance officially became law. The moment county leaders announced their intention to eliminate long-established vacation […]
Life of an Unemployed 41 Year Old Real Estate Agent
Celebrating Over 22 Years of Being “Unemployed” on Maui It was March of 2003. I got my real estate license when I turned 18. No salary. No guaranteed paycheck. Just me, a license, and the decision every morning to go find work. I was poor, hungry, and determined… Some call that having a PHD! Since then, for […]
A Local’s Guide to Maui Short-Term Rental Condos in 2025
The Maui short-term rental (STR) landscape is in a state of transition. Whether you’re an investor, second-home buyer, or current owner of a vacation condo, it’s more important than ever to understand how the latest rules and proposals may impact your investment. As someone who was born and raised on Maui and has spent decades […]
Just sold at Wailea Point – Villa 1501 for $8.655M
The Sayles Team had the absolute honor of representing the buyers of Wailea Point Villa 1501, which just closed on March 31st for $8,655,000! We couldn’t be happier for this amazing family, who truly deserve such an exceptional oceanfront property. This marks the second oceanfront sale for a direct oceanfront unit at Wailea Point so […]
How to appeal your Maui property tax assessment
If you own property on Maui, you may have noticed a sharp increase in your property tax assessment. Many non-residents feel they are being unfairly overtaxed by the county, and while appealing your assessment is a challenging process, it might be worth the effort. For official County information on the appeals process be sure to […]
Just sold in Kula – 592 Hapapa Road
We are thrilled to announce the successful sale of 592 Hapapa Road, an extraordinary property that perfectly embodies the essence of Upper Kula living! Located at 4200 feet from sea level, this agricultural estate, originally listed for around $5M, just closed at $4M which was an outstanding result for our buyer clients. Representing the buyers […]









