From Luxury Retreats to Building the Future of Vacation Rental Management at Gather with Andreea Grigore

It’s 2008. The financial world is crumbling, Wall Street is bleeding jobs, and a brand-new finance grad named Andreea Grigore is staring down a recession with no clear path forward.

Then, at a birthday party in Montreal, everything changes. She meets the founder of Luxury Retreats, one of the world’s first platforms for high-end villas, private islands, and over-the-top vacation rentals. A casual conversation turns into an unexpected offer — and what was supposed to be a stopgap job becomes a nine-year masterclass in luxury travel, entrepreneurship, and scaling a global brand that Airbnb would eventually acquire to form its Luxe division.

Fast forward, and Andreea is now the CEO of Gather Vacations, a company reshaping the playbook for property management. Instead of asking local managers to give up their independence, Gather powers them with the back-end systems, tech, and support they need so they can focus on what matters most: homeowners and guests.

In this conversation, you’ll hear:

• How a recession detour became a once-in-a-lifetime break into luxury hospitality
• The inside story of scaling Luxury Retreats and watching it become part of Airbnb Luxe
• Why Hawaii was the perfect test bed for rethinking property management
• How Gather’s model challenges the franchise status quo and sets a new standard for partnership
• What the future of vacation rentals looks like when brand, consistency, and local expertise collide

Explore Gather Vacations

Connect with Andreea

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.