Built by an operator. Run like a hospitality company.
The Kressley Group was founded on a simple premise: short-term rental properties perform better when they are managed at a hospitality standard — by people who understand both the property and the guest.
How We Got Here
The Kressley Group started in Toronto, where founder Brendan McKenna left a corporate career to pursue what he saw as a fundamental gap in the short-term rental market: most properties were being listed and cleaned, but almost none were being managed as genuine hospitality operations.
What began as a single property in a major urban market grew into a management company built around a specific thesis — that short-term rental properties are hospitality assets, and that treating them as such produces better outcomes for owners, better experiences for guests, and a more durable business for everyone involved.
Today, Kressley operates across select Ontario markets, with our deepest presence in Stratford — where we are the #1-ranked host — and a founding footprint rooted in the Toronto market.
Leadership
Brendan McKenna — Managing Director
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Brendan founded The Kressley Group after a career in [corporate background — Brendan to provide], recognizing that the growing short-term rental market lacked operators who combined hospitality discipline with property management expertise. He serves on the boards of Destination Stratford and the Accommodation Tourism Advisory Committee.
Vinny Donker — Director of Sales & Operations
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[Bio to be provided by Brendan]
What Guides Our Work
Selectivity over volume.
We do not accept every property. Every engagement begins with an evaluation, because our performance — and our reputation — depends on starting with the right foundation.
Hospitality standard, not listing standard.
Guest experience, property condition, and operational execution are managed at the level of a boutique hotel, not a rental listing.
Aligned incentives.
Our commission-based compensation model means we earn more when your property performs better. We have a direct economic interest in your success.
Operational depth.
We manage the full operational stack: guest communication, dynamic pricing, cleaning coordination, maintenance, compliance, and financial reporting. Nothing is outsourced to the owner.
Recognition & Involvement
#1-ranked host in Stratford (per AirDNA)
Board member, Destination Stratford
Member, Accommodation Tourism Advisory Committee
[Additional affiliations, awards, or recognitions — Brendan to confirm]
Want to know more about how we work?
We are happy to talk through our approach, our standards, and whether we might be the right fit for your property or project.