Frequently Asked Questions

Wisdom from the World's Top Vacation Rental Professionals

Welcome to most unusual FAQ video library of the most pressing vacation rental questions. Each video below was filmed with an acclaimed host from A Sense of Place / The Vacation Rental Show, the world's first vacation rental-themed travel show. Videos are organized by advancement level in order to streamline your learning experience. You can use the Table of Contents below or simply browse to get started...

Choosing The Right Property

What are good ways to do market research?

Ready for the most enjoyable market research ever? John recommends investing in a stay at the nicest vacation rental you can find. Take notes about the experience and how you can improve. Ask the host questions about how they operate and what products they use. Sit down at the end of the stay and create an Action List of next steps. Oh and in the process, don't forget to sit back and relax: this is the vacation rental industry after all.

What are the virtues of staying in vacation rentals when I travel?

When we travel, staying in other vacation rentals can provide great insight. Bradie always finds improvements and ideas when she travels. 

How can vacation rentals be such "a gamechanger"?

What do vacation rentals mean to Damien? They are a gamechanger. Not just in terms of income, but as a father, they make his travels less stressful and all-the-more enjoyable. 

How do I find the right property?

When considering investing in a vacation rental home, there are two layers of research that Nancy recommends: the first is to investigate city data such as crime, household income, taxes...etc. The second layer is the more granular vacation rental deep dive: browsing the major listing sites to gauge the supply (inventory) and demand (occupancy calendars) of the local market.

Why does local regulation matter so much?

San Diego has been dealing with tough regulatory battles now for some time. In this clip, Paul explains some of the more challenging elements of that predicament, but also the importance of a fighter mindset. 

How can fierce opposition to short terms rentals manifest itself?

Barcelona is one of the most controversial vacation rental cities in the world. Damien got to experience this up-close when one of his apartments was "infiltrated" by demonstrators -- he gives them credit for creativity. You can see the full article on this incident below...

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Personality Traits

Does this fit my definition of "a dream job"?

In our industry, many people do what they are super passionate about, they're incredibly good at it, and it earns them money. That is basically the picture-perfect definition of the dream job.

Why is being high maintenance good for this business?

When getting started in the vacation rental industry, it's hard to know exactly what guests will expect to be in your home. Nancy found that the easiest way to equip a vacation rental is to assume the role of "high maintenance" vacationer.

What does "pushing the envelope" look like?

Constantly look to improve your guest experience -- don't ever sit still or get complacent: this is one of the universal attitudes we've observed about the world's most successful vacation rental professionals. John is always on the look out for amenities or upgrades to his home -- in fact, he aims to have at least one improved element before any guest stays a second time.

Why is continual improvement obligatory?

Upgrades to your vacation rental properties should be viewed as investments. Not only are they generating better reviews, commanding a higher price per night, and setting you apart from the competitor down the street. But they are actually investment assets, increasing the overall value -- on paper -- of your business.

Why is validation so ingrained in this industry?

Validation is huge. And seeing the result of hard work is a really important thing. In many industries, professionals don't get enough of it. But in vacation rentals, our work is directly validated -- reviews are the vehicle for this validation and John considers his collection one of the most precious things he owns.

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The Background Experience

What if I don't have any experience?

So many people get started in the vacation rental industry as a result of adversity. When the recession hit, Darik lost his job in finance and Sally's work in design was down. "We had to come up with something," was the family's realization. This turning point, starting "out of necessity" is a common thread in so many accidental vacation rental stars career paths.

Have others fallen into this business "accidentally"?

Jim and Jennifer Kitts fell into their vacation rental business. After having their first child, then buying the family real estate company, and sniffing out the untapped potential of short term rentals, their innovations and trailblazing have created a well-rounded version of success.

Am I hospitable?

Damien got started with vacation rentals before Airbnb existed. He was hosting people in his home for the enjoyment (the income was fun too). While some of those original elements of his hospitality were unreplicable, it became something of a template for his now-thriving property management business.

Does a real estate background help with vacation rentals?

Like so many "accidental" vacation rental owners and managers, CJ started off professionally in hospitality. When family circumstances asked him to then dip his toes into real estate, he used it as a gateway into an industry which perfectly blends the two.

What if I feel naive and under-prepared?

Deciding to up and move to Hawaii was no obvious or scary task. And in hindsight, Amy and Scott attribute some of their decisions to naive youth. But in this case, the outcome was anything but irresponsible. In fact, it was that exact mindset which set them apart.

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Building A Support Team

Is it OK to weed people out?

For a small business, finding the right employees can be a long and arduous process. Unfortunately, there's no silver bullet or magic pill to the process. But as Frank and Kelly have found, weeding out those who don't seem to "get it" and doubling down on the employees that do -- this is the slow yet steady way to build a strong vacation rental team.

How do I form trusting partnerships?

Finding the right partners for a vacation rental venture can be challenging. And we've heard horror stories about choosing the wrong people. But Frank and Kelly seem to have lucked out with their partners Cassie and Mike: they all have their own strengths and above all else, seem to be proactive in getting stuff done.

The value of finding "a point person"

If you don't live in the same destination as your vacation rental, locals you can trust are worth their weight in gold. Even better when they're in the tourism business. Frank and Kelly were fortunate to meet Oliver of Xplore, a local adventure tour agency. A point person like Oliver, who meets guests upon arrival and facilitates activities during their stay, can lighten the managerial workload while enhancing the overall guest experience.

How much can one manager make a difference?

Hiring a new manager can be daunting. But Amy and Scott look back at the moment they hired Linda as the moment everything changed. When backed by a healthy dose of trust, a set of fresh eyes can mean all the difference.

What should I look for in employees?

One of the things we hear from a lot of professional VR hosts is "I wish I could duplicate myself." But can also be seen as a weakness of the business. Damien aims to "duplicate" himself using a balance of technology and in-person charm (in the form of staff). 

What are some of the secrets to remote management?

In addition to Your Welcome Tablet and the internet, Nancy practices a preemptive style of management that begins way before the guests arrive. She combines that with simple phone/text correspondence to ensure that guests are taken care of as well (if not better) than if she was living next door.

Can I manage my vacation rental business from another country?

Damien manages his Barcelona apartments from Berlin. This requires a unique dose of problem-solving in order to make sure things are smooth. Sometimes we see that managers from afar can teach on-site managers a whole lot (and of course, vice versa) because they're forced to break problems/challenges down to a molecular level. 

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Calibrating Expectations

What are the expected costs of doing business?

"The cost of doing business" is a phrase we heard from John several times. It can be easy to disregard small gestures like welcome snacks or courtesy drinks as additional expenses. But John views them as integral elements in the guest experience -- and so they are not added costs, but rather costs of doing business. Calculate these costs into your total nightly rate so that it's quite literally a line item in your business expenses.

Where do I draw the line between hobby and business?

Airbnb has cultivated this incredible generation of hospitality professionals. But it has also created a weird space in which some hosts feel like they're doing you a favor by letting you stay. When charging real dollars and competing with the hotel down the street, Damien believes there's a certain duty to run a true business in which the guest is always right. 

What should I expect from the learning curve?

When getting started, consider seriously the quality of items to put in your home. From a sheer investment standpoint, high-quality products that are durable end up costing you less in the long run. Nancy explains how this process takes time, but also some ways to speed it up. 

What are the lifestyle benefits of running a vacation rental business?

While the demands of the industry can be testing, vacation rentals afford Darik and Sally time with their kids, an avenue to pursue real estate investments, and the freedom to create their own balanced lifestyle. However, not unlike many avenues of entrepreneurship, it's not a walk in the park. 

What can vacation rentals bring to my life?

CJ's father once asked him this vital question: it was not just a pivotal moment in his professional career, but it ended up guiding the personal decisions CJ would make along the way.

What are some of the ups and downs I should expect?

The vacation rental industry isn’t for everyone. And it’s certainly not as easy or stress-free as it might appear. So when Jim walks us through the journey his family took to get here, it serves as a nice reminder that serendipity, combined with persistence through some of the harder times can be a recipe for great success.

What is a healthy way to define success?

One of the biggest “disrupting” factors about the vacation rental industry is that many hosts define success in ways other than cash flow. This “lifestyle” element of the business — getting to meet new people, pursuing passions, creating one’s own schedule — changes the terms of the playing field. It means hosts are making decisions through a different lens and the results are surprising.

How should I calibrate my goals?

Vacation rental business owners deal with all kinds of changes: market shifts, industry corrections, legal battles...etc. And it can be helpful to sit down to recalibrate your goals on a regular basis to account for all this chaos: Darik and Sally, for instance, find that their goals now are radically different than when they first started.

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The Guest Experience

How do I balance amenities and pricing?

What one single item gets featured the most in your reviews? Nancy says it's her towels. Splurging on extra comfortable towels is not just a way to generate 5-star's a way to command a higher nightly rate. 

How do I find a local touch?

Small touches like boutique soap and shampoo do indeed have a cost. But they also give a sheen of thoughtfulness to your vacation rental experience. They are the small touches that most other proprietors are not willing to do. And if you keep your eyes out for something local, and build the cost into your nightly rate, everybody wins.

Can a vacation rental look more like a boutique hotel?

Providing prepared meals at a vacation rental is not so common, due to the prohibitively high costs. But what Frank and Kelly discovered is that Hacienda Antigua has many of the same characteristics as a B&B: and that utilizing the on-site staff for small things like breakfast can make a huge impact on guests.

What so special about these makeup remover towels?

Running a vacation rental business can be frustrating, especially when it comes to sheets and towels: Frank and Kelly were faced with the challenge of women removing their makeup and staining luxury towels. So the two are considering one of those black "Makeup Remover" towels.

What business are we really in?

Many hospitality enterprises are in the business of making people smile. And by finding some of the other operations in your area that do it too, unique partnerships can emerge.

How can I really "wow" my guests?

Linda and Amy meet with their team once a week to review incoming guests -- to determine any special interests, motives, or qualities about the stay that might give hints on what "Wow" moment to curate. It's a signature initiative that has real impact on their bottom line. 

How powerful can reciprocity really be as a marketing tool?

As small business owners we're taught to sell, sell, sell and win, win, win. But in doing so, we realize that inevitably someone feels like they lost. Instead, Linda and Amy leverage the "help, don't sell" style of marketing, harnessing reciprocity and goodwill to draw the best kinds of clients forth.

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The Local Community

What is the "hub and spoke" concept?

CJ loves the metaphor of a hub and spoke: how when all parts are moving together in any organism, everybody pulls forward. This is a strong reminder to stay aware of your surroundings and the people and things that need to be involved.

How do I work with my competitors?

It can be easy to view our local nemesis as competition. But in Blue Ridge, CJ realized that all community members were actually in the same boat: create a prosperous destination and they all thrive. His spirit of unification is among the most progressive in the industry to date. 

Is there a way to give back to my local community?

All vacation rental managers possess a huge ability to impact the local community they call home. Playing on the idea of Pack for a Purpose, the team at Great Vacation Retreats contemplates asking guests to reserve a corner of their suitcases for donations to local causes. 

Can "giving back" be part of my business model from the start?


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Growing A Property Management Agency

What is "the partnership philosophy"?

CJ has a unique take on everyone he works with: from employees to property owners to guests. It's something he calls "the partnership philosophy" and it's a cornerstone of CJ's business model.

What is the primary mission for all property managers?

Property managers sometimes struggle to figure out who their "primary" client is: is it the owner of the property, or the guest themselves? At Bluewater, they believe that it has to be the guest -- this was something we learned from Luke at the beginning of the full episode. Learn here how the logic breaks down.

How do I upgrade to software?

In our industry, many people do what they are super passionate about, they're incredibly good at it, and it earns them money. That is basically the picture-perfect definition of the dream job.

How do I grow my team?

One of the most poignant lines of our entire visit: "If I'm going to invest in my company it's going to be in the people." CJ gives shows that in vacation rentals, it's less about the what and more about the who

Is there a "sweet spot" for property managers?

Strengthening one’s brand can be done all the time, and Jim is quick to point that out. But in terms of growing other elements of the business, Carolina Beach Realty recognizes the sweet spot it’s in: by tightening the bolts on the current variables, the Kitt’s create a more predictable and sustainable future.

What are the economics of in-person check-ins?

In person check-ins are not necessarily obligatory in the vacation rental industry: some companies use them because they can, other companies don’t use them for specific reasons. For a company like Seattle Oasis, the cost of one check-in is multiplied over many properties, making it prohibitively expensive.

What is "anti-scalability" and is it for me?

Figuring out the little things that will not scale is a core philosophy of the Limited Edition Theory. Here, we break down some of those elements that, while more expensive and less automatable, Bluewater uses with great success.

What are the virtues of developing in-house services?

Almost out of necessity, Frank and Kelly began to offer in-house services such as private chef, masseuse, and yoga: simply because those services were not available in town. But now that the local region has grown, these in-house services have improved. A vacation rental that offers in-house options lends an air of luxury, convenience, and distinction.

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