This week’s roundup covers Airbnb’s investment in WeRoad, Vrbo's latest AI features, proposed STR regulation changes in Tybee Island, Australia’s updated vacation rental tax laws, and new developments surrounding Bill 9 in Maui. Let’s dive in.
Meet Bianca Han, co-founder of Sapphire Vacations, a collection of luxury beachfront rentals in St. Thomas, U.S. Virgin Islands. After falling in love with the island in 2010, Bianca and her husband, Paul, built a thriving business by designing beautiful spaces and building efficient systems that allow them to manage everything remotely.
This week’s roundup covers Airbnb’s 2026 Summer Release, AI’s growing role in the guest booking journey, Booking Holdings’ long-term growth strategy, Nashville preparing for the 2030 Super Bowl, and a proposed statewide short-term rental tax in Illinois. Let’s dive in.
This week, we are featuring Tom May, founder of Fade Away Vacations. Tom has been partnering his business with OwnerRez since 2022, and what started as a small personal investment has grown into a portfolio of thoughtfully designed homes focused on helping guests “fade away” and create meaningful stays.
In Episode Thirteen, Paul and Chris break down the undervalued power of saying no and how that clears the way for the right yes. They talk through recent investment decisions, how their thinking has shifted over time, and how to recognize a property with the right “feeling.”
