10 Essential Questions to Ask Your Short-Term Rental Manager

Running a profitable short-term rental (STR) is more than great photos and stylish decor.

Behind the scenes, it takes systems, strategy, and day-to-day execution. For many owners, hiring a property manager is the smartest way to protect their investment and free up their time.

But not all managers are created equal. The right partner can maximize your revenue, protect your property, and deliver five-star guest experiences. The wrong one can drain profits and create endless headaches.

If you’re interviewing property managers, here are 10 essential questions every vacation rental owner should ask before signing a contract:

1. What services are included? What’s extra?

Some managers only handle bookings and guest communication, while others offer full-service packages that cover marketing, maintenance, and owner reporting.

Pro tip: Ask for a clear breakdown of what’s included in their base fee and what will cost extra (like deep cleans, linens, or after-hours emergency calls).

2. What technology do you use?

Modern STR management should include:

• Property management software (PMS)

• Dynamic pricing tools

• Automated messaging

• Smart home features like locks or thermostats

• Owner dashboards for real-time performance

Why it matters: The right tools save time, reduce mistakes, and keep you in the loop.

3. How do you structure your fees?

Some charge 20–30% of gross revenue, others a flat monthly rate. Ask about extra fees like onboarding costs, cancellation penalties, or upcharges on maintenance and cleaning.

Question to ask: “If I decide to end the contract, are there termination fees?”

4. How do you set and adjust pricing?

Pricing is the heartbeat of your rental’s revenue. A good manager should use dynamic pricing platforms and revenue management knowledge and strategies to adjust for seasonality, local events, competitor dynamics, and market shifts. Pricing adjustment should happen often.

HUGE Red flag: Managers who rely solely on dynamic pricing platforms, say they “set rates at the beginning of the year”, or managers who say they only adjust pricing occasionally.

5. How do you screen and protect against bad guests?

Effective guest screening prevents parties, damage, and neighbor complaints. Managers should use ID verification, minimum stay requirements, and security deposits or damage protection.

Why it matters: One bad stay can cost more than a year of management fees.

6. What’s your cleaning and maintenance process?

Guest reviews live and die on cleanliness. Ask if they:

• Follow checklists to ensure consistency

• Restock essentials between stays

• Schedule seasonal deep cleans and inspections

• Perform regular maintenance checks

Pro tip: Find out if they offer 24/7 emergency maintenance - a broken AC in July can’t wait in Florida!

7. How do you market my property?

Strong marketing goes beyond Airbnb and Vrbo. Look for managers who:

• Hire professional photographers

• Write optimized listing descriptions

• Use multiple booking channels

• Build direct booking websites for repeat guests

• Highlight unique amenities that set your property apart

Why it matters: More visibility = more opportunities for your place to get booked = higher occupancy and stronger revenue.

8. How will you communicate with me?

You should know exactly how your property is performing.

Ask: “Will I get monthly financial reports, access to a dashboard, and regular check-ins?”

Your manager should feel like a business partner, not a gatekeeper.

9. Can you show me results from similar properties?

A confident manager should provide:

• Revenue projections

• Occupancy benchmarks

• Average nightly rates

• References from current owners

Why it matters: You’re not just buying promises, you’re buying proven results.

10. Are you licensed, insured, and compliant with local regulations?

STR regulations differ by city and county. Your manager should handle permits, lodging taxes, and compliance requirements.

Ask: “Do you manage tax collection and remittance on my behalf?”

Non-compliance isn’t just inconvenient, it can shut your property down.

Final Thoughts

Your short-term rental manager isn’t just a vendor, they’re a business partner. The right partner will optimize your income, protect your property, and deliver five-star guest experiences.

When interviewing managers, use these 10 questions as your checklist. Pay attention not only to the answers but also to how clearly and confidently they respond. A professional manager will be transparent, data-driven, and fully aligned with your investment goals.

Free Resource for STR Owners

Want a ready-to-use version of these questions and more? Download our FREE STR Manager Interview Checklist containing 30 questions to ask and take it with you when interviewing property managers. This printable resource ensures you ask the right questions - and get the right answers - before you hand over your investment.

Grab your free checklist below: