About Towanda Stays

Towanda Stays was born from a deep love of travel, a decade of Airbnb hosting, and a desire to create truly exceptional guest experiences.

I’m Hailey, the founder of Towanda Stays. My journey began in a spare bedroom in Toronto and grew into managing thoughtfully designed homes in both Toronto and San Miguel de Allende, Mexico.

Before launching Towanda Stays, I spent nearly 10 years at Shopify, leading everything from events and product launches to brand campaigns and retail strategy. That experience shaped how I approach hosting — combining strong systems with storytelling, creativity, and an eye for detail.

I’ve travelled to 48 countries, staying everywhere from rustic hostels to five-star resorts like Richard Branson’s Necker Island. I’d always take notes and photos, capturing the small but meaningful details — a welcome basket with fresh fruit when you arrive hungry, a hook placed exactly where you need it, or a perfectly curated guidebook full of local gems. Those touches left an impression. They’re the kind of moments I now bring to every space I manage.

Towanda Stays is a people-first, systems-led service rooted in intentional design and seamless hospitality. Whether you’re a guest or a homeowner, we’re here to make the experience easy, elevated, and unforgettable.