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 […]
Tag Archives: wailea condos
Maui H3/H4 Zoning update – What vacation condo owners need to know
What’s actually happening with Maui vacation rental condos and the new H3/H4 zoning? There’s been A LOT of noise surrounding this issue over the past couple years. And if you own a Maui condo, are thinking about selling one, or are considering buying one, it can be difficult to separate the facts from the headlines. […]
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 […]
Hoolei Villa 99-5 Epitomizes Upper Level Value
Hoolei Villa 99-5 offers Elevated Living in Wailea’s Premier Resort Community Hoolei Villa 99-5 aka The View from the Top There are views, and then there is the view from the 4th tier of Hoolei. If you’ve spent any time in Wailea, you know that elevation is everything. Villa 99-5 sits on the “top row,” […]
La‘i Loa 4C is Your Front-Row Seat to Wailea Living
Positioned in what we here at the Sayles Team consider one of the most desirable buildings within the community, La’i Loa 4C (also known as 30-201) is a standout in every sense. This second-floor corner residence delivers panoramic views that stretch across the Pacific Ocean and down the lush fairways of the Wailea Blue Course. […]
Villa 57-2: Sayles Team Closes First Ho’olei in 10 Months
The Sayles Team has once again proven their unrivaled expertise in the Ho’olei community with the successful closing of Villa 57-2 for $4,150,000 on April 4, 2025. This marks the first sale in the coveted neighborhood in over 10 months—since the sale of Villa 69-4 in May 2024 for $5,750,000, which was also represented by […]
Rediscover The Revitalized Spoon & Key Market!
Reflecting the ever-evolving landscape of our Wailea culinary scene, a beloved South Maui favorite has embarked on an exciting new journey. The Market Maui, formerly nestled in the Wailea Gateway Center, recently made a significant move—and rebrand—to become Spoon & Key Market. Now located a stone’s throw away from some of the more popular Wailea […]
Discover Unmatched Luxury at Wailea Point 2004
Nestled in the heart of South Maui, Wailea Point 2004 is a singularly magnificent villa offering breathtaking views of the main pool pavilion and the grand expanse of the Pacific Ocean. This exceptional property, in one of the more prestigious Wailea condo communities, is ideally located just steps away from a host of on-site amenities […]
Expansive Ocean Views and Luxury Living at Ho’olei 69-3
Designed for Elegance: Inside Ho’olei 69-3 Experience the pinnacle of luxury living in the heart of South Maui at Ho’olei 69-3. This exquisite town home is a rare gem in the highly coveted hotel-zoned community, offering a unique blend of modern elegance and thoughtful design. With three bedrooms and 3.5 bathrooms, this villa not only […]









