Seasonal Living, Reimagined 

By Sean Landreth, CEO & Founder, Seasonal Properties and Founder, Property Valet

How tech-enabled escapes are reshaping the way we live, work, and travel 

In today’s world, the traditional idea of a single “home base” is quickly evolving. With flexible work schedules, remote access to business tools, and a surge in digital platforms designed to support working from anywhere, more people than ever are embracing the seasonal lifestyle—moving fluidly from one inspiring destination to the next. 

This shift, once reserved for the ultra-wealthy or retirees, has become accessible thanks to technology, vision, and the right support systems. At Seasonal Properties, we’ve seen how monthly and longer-term rentals are transforming travel, investment, and lifestyle choices for modern families, entrepreneurs, and experience-driven professionals. Whether it’s golfing in Scotland, hiking volcanic peaks in the Azores, skiing on the Escarpment, or swimming in Georgian Bay, our clients aren’t just vacationing—they’re living seasonally. 

One of the most exciting changes we’ve seen in real estate and hospitality is the transition from static homeownership to dynamic, experience-based living. Technology has removed many of the logistical barriers that once made seasonal living difficult. Cloud-based booking platforms, international payment gateways, remote security systems, digital concierge services, and instant communications mean that guests can enjoy high-quality seasonal stays with peace of mind— whether they’re in Ontario, Portugal, or the Scottish countryside. 

A family from Collingwood can now book a farmhouse on the cliffs of São Miguel and work or school remotely while immersing in a new culture. A couple from Toronto might spend spring playing links courses in Scotland, renting a luxury stone cottage near St Andrews for a month, complete with fast Wi-Fi, curated experiences, and local hospitality. These aren’t quick vacations—they’re immersive lifestyle chapters. 

My own journey into seasonal living started right here in Ontario’s Georgian Bay region—a place that continues to shape our company’s ethos. With four seasons, world-class skiing, championship golf, fresh lake air, and the charm of towns like The Blue Mountains, Meaford, and Collingwood, Georgian Bay has always been a microcosm of seasonal living at its best. 

In winter, families cozy up in Scandinavian-inspired chalets, with days filled with skiing, snowshoeing, and hot chocolate by the fire. In summer, those same properties open their decks to lake views, morning rounds at Lora Bay and Cobble Beach, and evening walks along the waterfront trails.

It’s not just inspirational—it’s livable. With great restaurants, local culture, and more professionals choosing to work remotely from their chalets or rentals, it has become a Canadian case study in seasonal living.

At Seasonal Properties, we’ve taken this philosophy global. As more people opt for experiences over material accumulation, we’re curating month-plus stays in places that offer not just beauty, but meaning. The Azores—a rugged Portuguese archipelago—is one such place. Guests live in lava-stone cottages surrounded by hydrangeas, explore waterfalls by day, and soak in hot springs by night—all while managing their businesses via seamless tech infrastructure. My wife Eva and I experienced this recently, and it was surreal and inspiring.

While we were there, I thought of another favourite spot— Scotland—which offers a different kind of richness. Between rounds on storied golf courses, guests stay in restored estates or shepherd’s huts in the hills of Fife or the Cairngorms. These are places steeped in heritage, yet fully equipped for modern living. 

What ties these destinations together is the quality of life they offer—the ability to settle in for more than just a quick getaway. Monthly or seasonal rentals let travellers slow down, engage with their surroundings, and feel part of a community, even if just temporarily. 

As this mindset grows, we’re seeing the rise of the lifestyle investor—individuals or families purchasing properties not just for return, but for the lifestyle they offer. These properties are often in destinations they love to return to, but when not in use, they’re available through platforms like ours to other travellers. 

It’s a win-win model: owners gain flexible income and long-term appreciation; guests enjoy access to unique properties they can treat like home. With management systems in place—from full-service marketing to guest relations and property oversight—owners can be as hands-on or hands-off as they like. 

We’re helping Canadians purchase cottages in the Azores, ski homes in B.C., and waterfront escapes in Nova Scotia—all tailored to their lifestyle ambitions. These properties are part of a larger, curated ecosystem that guests can move between, season after season. 

The backbone of seasonal living today is smart, intuitive technology. Our properties feature high-speed internet, remote workspaces, smart locks, climate control, and 24/7 support. We also offer 3D walkthroughs, drone previews, and curated guides so guests can book with confidence. 

But I want to do more. I want our clients to feel even more comfortable booking these amazing opportunities. We’re always looking for tech that will help us improve. 

On the back end, our systems let homeowners view bookings in real time, track income, and coordinate with our team for updates, deep cleans, and guest feedback. Technology doesn’t just enable seasonal living—it elevates it. 

In the wake of global shifts and new work paradigms, more people are asking: Where do I truly want to live, and how often? Increasingly, the answer is not one place, but many—connected by seasons, interests, and values. 

Seasonal living allows people to design a year around what matters to them—skiing in the winter, golfing in the fall, or being closer to family over the holidays. It brings new perspective, healthier routines, and a deeper appreciation for the world’s diversity. 

At Seasonal Properties, our goal is to keep building a trusted network of extraordinary homes, supported by technology and local expertise. We envision a world where a well-designed lifestyle isn’t about being tied down—but opened up to cultures, landscapes, and moments that define us. 

To those curious about living seasonally, I encourage you to take the first step. Whether it’s winter in Georgian Bay, a month in the Scottish Highlands, or summer in the Azores, the world is closer—and more livable—than ever. 

You bring the dream. We’ll bring the keys. E