The Only Questions That Actually Matter When Hiring a Vacation Rental Property Manager

If you’ve searched online for how to hire a vacation rental property manager, you’ve probably come across articles with 50 or even 100 questions to ask.

Honestly, most of them don’t matter.

Things like years in business, office size, software, or how many employees a company has don’t tell you whether your vacation rental is actually going to perform.

After nearly 5 years in this business, I’ve found that homeowners really care about two things. They want to maximize their rental income, and they want to know their property is being taken care of.

Everything else comes back to those two goals.

In my experience, there are five areas that make the biggest difference:

• Unique Offerings
• Marketing
• Cleaning
• Maintenance
• Pricing

If a property manager is strong in those five areas, you’re probably talking to the right company.

So instead of asking fifty different questions, focus on these nine.

Unique Offerings

Start here because this tells you how the company thinks about its business and, ultimately, how they’ll treat your property.

1. What guarantees do you offer related to revenue performance?

A company that’s confident in what they do should be willing to stand behind it. You’ll come across many companies that offer a complimentary rental projection, including us. 

These are great and I highly recommend getting them. However, just because Company A gives you the highest number doesn’t mean you should go with them. 

Proof that they’ll be able to produce that number is usually hard to trust. Again, anyone can put numbers on a paper and say “This is how we’ll improve your revenue by 20%.”

Instead, look for a performance guarantee or a revenue guarantee. You want something that will have an impact on the revenue they’re earning from you if they don’t hit the numbers they projected. 

If the answer is simply, “We’ll do our best,” I’d keep asking questions. A good company should be able to explain their guarantees clearly and give real examples of how they work.

2. What makes you different from other companies?

Almost every property manager says they have great customer service for their owners.

That’s expected.

Instead, ask what actually separates them from the competition.

Maybe they generate a large number of direct bookings, will send you monthly performance or review reports, or offer services other companies don’t.

Whatever their answer is, it should be specific.

Marketing

Marketing has one of the biggest impacts on your rental income because an empty calendar doesn’t make money.

A good property manager should have a strategy for attracting new guests while also encouraging previous guests to come back year after year.

3. How do your bookings break down by channel, and what percentage of guests come back?

Ask where their bookings come from.

A healthy mix of Airbnb, Vrbo, Booking.com, direct bookings, and other sources is usually a good sign.

Then ask what percentage of guests return each year. Look for a number in the 20% – 30% range. 

Think about this way: if you can fill 25% or so of your calendar each year with repeat bookings, you can really start to push the prices on the remaining available dates. It’s supply and demand. If you have less available, you can charge more. 

Repeat guests are some of the most valuable bookings you’ll ever get. They’re more likely to book directly, cost less to bring back, and often become long-term customers.

4. What do you do outside Airbnb, Vrbo, and social media to generate bookings? Can you show proof it works?

Listing properties on Airbnb and Vrbo is the minimum.

The better question is what they’re doing beyond those platforms.

Do they invest in SEO?

Email marketing?

Google Ads?

Partnerships with local businesses?

Most importantly, ask for proof. If they say they make great videos, go check out the videos. If they say we have a partnership with a golf company, have them send you a report of how many bookings came from that company last year. 

A good company should be able to show real examples instead of simply saying they market properties well.

Cleaning

Cleaning has a direct impact on guest satisfaction.

A clean property leads to better reviews, more repeat guests, and stronger rental performance over time.

You need great cleaning reviews, ideally a 4.8 on AirBnB or above, to have a successful rental. 

5. How do you maintain quality control on your cleaners?

Cleaning is a difficult and sometimes disgusting job. I can tell you first-hand that cleaning crews burn out quickly and their quality goes with it. 

The important question is how they verify every clean meets their standards.

Do they inspect every clean? It’s okay if they don’t, but what is their process. 

Do they use checklists?

Do cleaners submit photos after each turnover?

You want to know there’s a system in place that catches problems before guests arrive. 

Also, ask where you can see their AirBnB reviews. Look for most listings to have a 4.7 or above. 

6. If there’s a cleaning issue, how exactly do you handle it?

Even the best cleaners make mistakes from time to time.

The difference is how quickly the company responds. In most cases the cleaners should be going out same-day when there is an issue. 

Ask what happens if a guest checks in and reports a problem.

Who gets notified?

How quickly can someone get there?

Do they have cleaners available after hours?

A company with a good process should be able to answer these questions confidently.

Maintenance

Marketing gets bookings.

Cleaning earns great reviews.

Maintenance protects your investment. Myrtle Beach isn’t an ultra, high-end destination and the visitors we get can be careless at times. 

A good property manager should be focused on preventing problems before they become expensive repairs.

7. How do you protect my home and prevent expensive maintenance problems?

Ask how they handle guest damage. The best companies offer owners some damage protection coverage. Usually it’s anywhere between $1500 – $3000 per reservation. It just depends on the guest. 

It’s hard for a company to share proof on how well they maintain homes so I would look again at their reviews. If their reviews are high, it usually means they are doing well with maintenance at the properties. 

Companies get a bonus if they can share a detailed preventative maintenance program that they stick to. 

Preventive maintenance protects your investment and helps avoid expensive surprises down the road.

Pricing

Pricing isn’t something you set once and forget.

Demand changes throughout the year, and your rates should change with it.

The best property managers combine technology with local market knowledge to maximize revenue.

8. Can you provide projected revenue and expected annual expenses?

Before hiring anyone, ask them to prepare projections for your property.

They should estimate rental income using comparable homes they already manage.

They should also provide expected annual expenses, including:

• Cleaning
• Maintenance
• Pool service
• Landscaping
• Linens
• Deep cleans

The numbers should be based on your property, not a generic estimate.

9. How often do you review and adjust pricing?

Ask how often they review pricing.

The best managers don’t rely on software alone. They should be looking at things monthly at a minimum. 

We adjust our prices based on occupancy goals. If we are below a goal for a certain month and we know we are in a period where we should be getting bookings, we’ll bring down the price. 

Pricing isn’t rocket science but you need to be monitoring data constantly to have a good pulse on the market. 

You can miss out on a lot of bookings if you aren’t adjusting prices consistently. 

Conclusion

You don’t need fifty questions.

You need these nine, asked directly, with follow-up questions when the answer is vague.

A great property manager should be able to answer each one confidently, explain their process clearly, and back it up with real examples.

There’s nothing better than hard proof. 

If every answer sounds vague or generic, I’d keep looking.

Focus on these five areas:

• Unique Offerings
• Marketing
• Cleaning
• Maintenance
• Pricing

Get the answers to those five areas right, and the rest of the relationship tends to take care of itself.

At the end of the day, the right property manager should help you maximize your rental income while protecting your investment. Those are the two things that matter most.