Questions to ask before handing over a holiday let

You've got a property that could work as a holiday let, or you're already managing one but thinking about handing it over to a professional. Either way, the conversation with a potential manager will make or break the decision. The right questions won't just fill dead air—they'll reveal whether this person actually understands your property, your expectations, and the work involved. Here's what to ask, why it matters, and what to listen for.

What systems do you use to track bookings and payments?

A manager who fumbles this answer or vaguely mentions "a spreadsheet" is already a red flag. You need to know whether they use dedicated short-let software, how they handle guest communication, and crucially, how and when you receive your money.

A strong answer names a specific platform—maybe Airbnb's tools plus Booking.com integration, or a management system that pulls data across channels. They'll explain how often you're paid (weekly, fortnightly, monthly), whether they hold a separate trust account, and how invoicing works. They should also mention how they track occupancy and pricing in real time. If they're evasive about payment timing or dismissive about systems, walk away.

How do you handle last-minute cancellations or guest disputes?

This matters because your income depends on it, but so does your peace of mind. A manager who says "guests cancel sometimes, that's just the business" hasn't thought this through. You need to know their actual strategy.

Listen for specifics: do they have a cancellation policy in place, and will they enforce it fairly? How do they respond to a guest claiming the property doesn't match photos, or that something is broken? Do they have authority to issue refunds, or do they escalate to you for every complaint? What's their timeline for resolving disputes? A manager confident in their process will walk you through a scenario and explain where the responsibility sits. They should also confirm they manage the review-and-response cycle so negative feedback doesn't sit unanswered.

Who cleans between guests, and what's the standard?

This is where dreams meet reality. A manager's cleaning protocol determines whether your property stays booked and your guests stay happy.

Ask whether they employ dedicated cleaners, use a rotation of contractors, or outsource to a cleaning company. Request specifics:

• How many hours do they budget per turnover?
• What's included in a standard clean versus a deep clean?
• Do they inspect the property after every guest, or spot-check?
• How quickly can they turn the property if a guest checks out early and another arrives the same day?
• What happens if a guest damages something or leaves the place unusable?

A manager should also explain how they manage the cleaning supplier relationship—do they pay the cleaner directly, or invoice you? If something goes wrong (a guest leaves stains, items go missing), who investigates and who pays? Good answers are detailed and honest about turnaround time. Vague answers like "we keep it clean" mean nobody's accountable.

What's your process if the property needs repair or maintenance?

Propertyies break. Geysers fail, locks jam, plumbing backs up. You need to know whether your manager can handle an emergency without leaving your guests in the dark or your costs spiralling.

Ask whether they have a roster of trusted tradespeople on speed-dial, or whether they'll source someone on the spot. Do they get quotes before authorising work, or do they have a spending threshold above which they contact you first? How quickly can they organise an emergency repair—same-day, next-day? Will they stay in communication with you and the guest throughout?

Then ask the financial question: if a repair costs more than expected, who decides whether to proceed? A manager worth hiring has relationships with plumbers, electricians and maintenance people already, knows what things typically cost, and won't wait for your approval while a guest is without water. But they'll also respect your budget and explain decisions after the fact.

These four conversations will show you whether a manager sees your property as their responsibility or as a job they're handling for you. The best ones answer with examples, admit what they don't handle themselves, and ask you questions back. When you find someone like that, you've found a partner worth trusting. Start your search on Strove, where you can vet managers by their reviews, verify their credentials, and read what other property owners experienced with them.