Successful Vacation Rental Management: Expert Insights From Top Short-Term Rental Leaders 

Industry Insights, Property Manager Tips
Successful Vacation Rental Management: Expert Insights From Top Short-Term Rental Leaders 

Whether you’re just starting out in the field of vacation rental management or trying to revamp your existing business, getting some advice from successful property managers is always a good idea. Check out some helpful insights from some top notch leaders in the property management space.

Go Beyond the Title

Some of the best advice from property managers has to do with your mindset. Jeremy Gall, the founder and CEO of Breezeway, has an interesting take on the job title. He says, “[t]he title ‘property manager’ sounds really transactional and I think it under serves a lot of the work that people in the industry give.”

If you want to be a successful property manager, it’s wise to look at the field the same way Gall does. Great property managers don’t just sit back and handle bookings from afar. They strive to provide incredible hospitality for every single guest who stays at one of their properties.

Interestingly enough, Airbnb CEO Brian Chesky says that his company went wrong when he and other executives became further removed from customers: “We went from us talking to customers, to hiring people to talk to customers, to people who manage people who manage people who talk to customers.”

That’s not to say you shouldn’t hire employees to talk to your customers. However, as your company grows, it’s a good idea to make sure you’re still connected with the day-to-day of your business.

Focus on the Guest Experience

You want each of your properties to make a great impression on your guests. After all, the happier a guest is with a stay, the more likely they are to return — and to tell their friends!

George Tarnopolsky, Global Service Operations Leader at Tokeet, says that “[a]t the core, we are always thinking about the user experience — and ultimately, guest experience too.” 

When you think about the guest experience, you probably imagine great amenities, fluffy towels, and activities nearby. But even seemingly tiny touches can shape the guest experience. According to Ashley Kubiszyn, CEO of River Ridge Rentals, “Guests are more willing to communicate things over text message, and it takes a lot less work to send a text than it does to make a phone call.” 

Most guests appreciate that you’re checking up on them and that you can do it via text.

Make Your Properties Work for You

The Facebook page for Uplisting, a rental management platform, has a pithy bio: “Short-term rentals should be working for you, not the other way around.” It might sound like a cliche, but it does capture an important truth of property management — if you’re run ragged and feel like you’re working for your rental properties, there’s something amiss. 

Maybe your business has grown enough that you need an employee or two. Or maybe you’re barely scraping by because you’re pricing your properties too high for the market. It can take some trial and error to develop a successful management strategy, so don’t give up!

Another way to make sure you’re prepared for the unexpected is to keep your properties protected with a customized short-term rental insurance policy from Safely.

Be Mindful of Seasonal Demand

Many tips from property managers address situations you run into after you buy a rental property. But what about before you’ve purchased one? Before you invest in a short-term rental property, you should size it up carefully. It’s easy to get carried away with the possibilities. For example, if you invest in a beachside home, there’s a good chance it will be booked solid all summer long.

Gu Riva of Lofti encourages anyone thinking about investing to consider seasonal demand. He says, “Short-term rental rates can fluctuate based on seasonal demand. Research the peak and off-peak seasons in your location to adjust rates accordingly.”

Ideally, you’ll be able to find an investment property that has at least some desirable features every season. For example, if you’re considering a beach house, you already know it will draw in visitors over the summer. 

If there’s a nearby town with restaurants and other year-round attractions, your guests will have something to do in any season. Assuming everything else is equal, a beachside home with a nearby town is usually a better investment than one with no attractions nearby.

Service, Tech, and Pricing Matter

Jeff Nisuis owns a company called Titan Beach Rentals, and he has worked as both a property manager and business owner. During his time in the industry, Jeff was able to distill his knowledge into three simple points. “I’ve pinpointed three pivotal aspects that spell success for your enterprise,” he says. Here they are:

  • Customer service and follow-through is essential — especially promptly responding to guest messages and calls
  • You should have a well-rounded suite of modern technology — the most important is a quality property management system (ideally one that can automate some functions)
  • Accurate pricing is vital — the best way to price accurately is to use a dynamic pricing tool that automatically decides rates based on market conditions

This succinct, three-pronged piece of advice is one of the better tips from property managers out there.

Safety Matters

Many guests simply take safety for granted. But as a property manager, you have a duty to make sure the premises are safe at all times. From installing carbon monoxide detectors to repairing a wobbly step, every action matters. Safely CEO Andrew Bate notes that having short-term rental insurance with a guest screening component answers the two most pressing questions that homeowners have, “Who is staying in my home and what happens if something goes wrong?”

Justin Ford, the Director of Safety Programs at Breezeway, has an interesting take on safety. He states that because the short-term rental industry has grown so fast, hosts often don’t have the safety features guests want.

Ford says, “I think that property managers who are taking the steps to make their properties safe have a huge opportunity to broadcast that and share with their guests that staying with them will meet their expectations.” Essentially, you shouldn’t just install safety features — you should make sure your guests know about them!

Get the Right Coverage (and Peace of Mind) With Safely

You might not have heard many inspirational quotes from property managers about insurance. And surprisingly few pieces of advice from property managers suggest you get an insurance policy.

However, whether you manage one rental property or one thousand, the right short-term rental insurance is an absolute must. Safely’s Protection Plans with commercial insurance and guest screening included are designed for property managers just like you. Get a quote today!

Safely’s Short-Term Rental Protection

Predictable coverage for unpredicable moments
Get A Quote
Amanda is a licensed insurance agent and the Vice President of Sales at Safely and has been with the company since 2021, leading new client onboarding and client initiatives. She is especially proud of her team’s efforts to successfully drive down annual churn to 3% with a trending net revenue retention rate of 130%. Outside of Safely, you may catch a glimpse of Amanda playing a nurse on TV, prepping for her next art show, or on a date with her husband of 16 years.

Related Resources

What to Do When Your Rental Property Has Water Damage
Industry Insights, Property Manager Tips

What to Do When Your Rental Property Has Water Damage

Guest Screening vs. Airbnb ID Guest Verification
Guest Screening, Property Manager Tips

Guest Screening vs. Airbnb ID Guest Verification

The Essential Vacation Rental Inventory Checklist [+ PDF Download]
Property Manager Tips

The Essential Vacation Rental Inventory Checklist [+ PDF Download]

Tax Implications of Short-Term Rental Ownership
Industry Insights

Tax Implications of Short-Term Rental Ownership

Search Engine Optimization: A Guide for Short-Term Rental Property Managers and Hosts
Property Manager Tips

Search Engine Optimization: A Guide for Short-Term Rental Property Managers and Hosts

Best Tips for Staffing Your Growing Property Management Company
Property Manager Tips

Best Tips for Staffing Your Growing Property Management Company

Subscribe to our articles

Loading ...