How It Works
From first conversation to ongoing management — here is what the process looks like, and answers to the questions we hear most often.
The Process: From Conversation to Management
Phase 1 — Discovery
We start with a conversation about your property, your goals, and your situation. We ask questions about the asset, the market, and what you are hoping to achieve. There is no cost and no obligation.
Phase 2 — Property Evaluation
We assess the property against our management criteria: financial viability, market quality, design suitability, and amenity standards. If the property is a good fit, we move to a proposal. If it is not, we will tell you directly and explain why.
Phase 3 — Proposal and Agreement
We present a management proposal tailored to the property — including scope, operating standard, and fee structure. If both sides agree, we formalize the engagement.
Phase 4 — Onboarding and Launch
We handle the operational transition: listing optimization, professional photography, pricing setup, cleaning coordination, guest communication systems, and everything required to bring the property to our operating standard. You hand off the day-to-day. We start managing.
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We manage short-term rental properties — from individual homes and lofts to multi-unit developments and boutique hospitality projects. We also offer residential property management for long-term rentals. Every property we take on must meet our management criteria through an initial evaluation.
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We operate across select Ontario markets, with our deepest presence in Stratford and a founding footprint in the Toronto market. We evaluate opportunities based on market quality and asset fit, not geography alone.
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Kressley operates on a commission-based model, aligning our incentives with the performance of your asset. Because every property, market, and opportunity is different, each engagement is scoped based on operational complexity, growth potential, and the level of hospitality execution required. Our fees reflect the scope of a full hospitality operation — not a listing-and-cleaning service.
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Our management agreements are designed to be fair and transparent. The specific terms — including duration, notice period, and scope — are tailored to each engagement and discussed during the proposal phase. We believe the quality of our work should be the reason you stay, not the terms of a contract.
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No. We evaluate every property before taking it on — assessing financial viability, growth potential, design suitability, and amenity standards. This selectivity exists because our compensation is tied to performance. We have a direct interest in starting with properties where we can deliver results.
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Once we agree on an engagement, we handle the full operational transition: listing optimization, professional photography, pricing setup, cleaning coordination, guest communication systems, and everything required to bring the property to our operating standard.
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We provide 24/7 guest communication and emergency support. Guests contact us directly — not you. We manage all guest interactions, from check-in to checkout and everything in between.
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Regular financial and operational reporting covering revenue, occupancy, expenses, and net returns. The frequency and format are established during the proposal phase based on your preferences.
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Yes. Owner use policies are established as part of the management agreement. We coordinate personal use around the booking calendar to minimize revenue impact.
Frequently Asked Questions