A bad property manager can be worse than no manager at all — you find out about problems late, from guests instead of from them, and by the time you notice something’s wrong, it’s usually already cost you money or a booking. A good working relationship with a manager should feel like a professional partnership: transparent, responsive, and easy to check on whenever you want. Here’s what’s worth asking before you sign anything, wherever your property is.

Licensing and legal standing

Ask directly whether they operate under the current local short-term rental framework for your property — for example Alojamento Local in Portugal, or the regional registration and CIN code system in Italy. These rules vary by municipality and have been changing in several regions, so a manager who can’t answer this clearly, or who waves the question away, is a red flag. Also ask what liability insurance they carry, and what happens, concretely, if a guest causes damage or there’s an incident on the property.

How they report, and how often

Ask to see a sample monthly report before you commit — occupancy, revenue, expenses, upcoming bookings. Ask how you’ll access your own calendar (you should always be able to see it, not request it). And ask what their actual response time looks like, both for guests and for you, not just what it says in a brochure.

How the fee actually works

Flat fee, percentage of gross revenue, or percentage of net — each has very different incentives built into it. Ask exactly what’s included, and what gets billed separately: cleaning, laundry, guest turnover, maintenance call-outs, emergency repairs. Get the full breakdown in writing before you sign, not after your first invoice.

A good manager will welcome every one of these questions, because the answers are exactly what they’d want a prospective owner to know.

Who’s actually doing the work

Is cleaning in-house or subcontracted? What does staff turnover look like? Is there someone genuinely on the ground near your property, or is it managed remotely from a call centre? And who handles a burst pipe or a lockout at 2am — by name, not by department.

References, not testimonials

Testimonials on a website are curated. Ask instead to speak directly to one or two current owners — ideally ones who’ve been with the company for at least a full season, not just their newest, happiest client. Any manager confident in their own service will arrange this without hesitation.