VRS198 – Selecting the Right Property Management System for your Vacation Rental Business with Terry Whyte

If you asked a property manager what the hardest decision has been in their business so far, most would put choosing reservation software, right at the top. Not only is it a big financial decision, but the time taken in implementing a new platform and learning how to use the software can be a huge drain on resources.

We only have a limited amount of time available to us, and there are so many calls on that time. Carving out chunks of hours to watch demos; to speak to reps who only have one goal – to sell their product (regardless of your actual needs), and sit through on-boarding webinars, is challenging. Making the wrong decision is very costly.

Terry Whyte is a homeowner of property on Anna Maria Island in Florida, and he’s also a successful property manager who credits some of that success to the research he did before selecting his PMS. According to Terry, this is not a simple process because you have to know what you want the platform to do for you before you start. A lot of thought needs to go into the features you want, because every PMS is going to focus on its bells and whistles rather than the real meat of the system that will free up your time and make life easier for you.

This interview supplements a recent article Terry wrote for the Vacation Rental Marketing Blog (see link below), so it is worthwhile taking a look at this for some additional information. He talks about the wealth of advantages gained for a VR business by using a good property management system – these include time-saving, good process management, channel management, and email automation – and what a good software platform can offer in terms of features.

Terry also shares:

  • The story behind his stunning new website
  • What to look for in a property management system
  • His favourite technological resources
  • A simple reflection on channel management ( and why you may not need them at all)
  • The industry experts who contributed to his success
  • The 3 tips he would give to a start-up manager


Links mentioned in the episode:

Choosing the Right VR Software on VRMB

Anna Maria Island Condo Rentals

Boomerang for Gmail

Rentals United

Vacation Rental Secrets/Web Design

Alan Egan

VRS197 – The Essentials of a Vacation Rental Guest Agreement with Bryan Geon of Vacasa

We protect our homes in many ways with safety and security systems; video cameras; apps to prevent overcrowding or noise; monitors to prevent overheating or freezing; smoke and CO2 alarms etc., but how many vacation rental owners have a guest agreement?

If my last few reservations are anything to go by, it’s not as common as I would have expected with independent homeowners, so I was pleased to be able to discuss this at length with someone in the know.

[Read more…]

10 Keys To Vacation Rental Success


Vacation home owners are facing challenges if they need to sell.

Many are turning to rental as an alternative to having a property on the listings for many months.

There are a large number of owners choosing this route because they have either tried selling, or are not prepared to lower their asking price and want to ride out the economic decline by renting for a few years but the road to vacation rental success is a long one.

This creates an interesting situation as there will be a lot of new properties coming into, what is already a competitive market, and owners considering this option need to work hard to compete effectively and achieve vacation rental success.

Despite the current economic conditions, a well presented and effectively marketed property should have no challenge in renting in the traditional high season periods but to be successful, owners must also attract the elusive out-of-season renters and convert enquiries to bookings.

Renters have high expectations of a vacation home. Just having good waterfront is not sufficient – hi speed internet; a dishwasher; laundry facilities and satellite TV are high on criteria lists.

Fully equipped kitchens, top quality mattresses and a selection of non-motorised watercraft are expected as standard.

These keys to success are the basics to getting set up and achieving good occupancy. [Read more…]

VRS196 – Vacation Rental Insurance Explained with Darren Pettyjohn

Insurance may not seem the most exciting of topics but it is one that impacts every single one of us, whether it’s a single condo or multiple properties. The moment we exchange our property (or a part of it) for money, we are in business, and that brings with it all manner of risks.

In my day-to-day work as a property manager, I talk to many owners who are interested in renting out their homes and am often surprised at how little they have thought about insuring the property. Many think that their general home-owners policy will cover them for rentals without understanding the wider implications of operating in the short-term rental market, and what liability issues they may face.

In this episode of the podcast Darren Pettyjohn of Proper Insurance joins me to talk about what this means to every host and vacation rental owner.

Darren has been in the insurance industry for many years and specialises in vacation rental cover so we discuss every aspect of risk; what negligence means; when and how you could be sued, and the costs involved if you are, plus much more.

Darren shares:

  • The differences between a landlord policy and short-term rental cover
  • What premise liability means and the relevance to your vacation rental business
  • Why a home-owners policy could leave you uncovered
  • Why you are unlikely to have business loss coverage in the event of a hurricane
  • What supplemental insurance is and how it fits into the vacation rental industry
  • How short-term rental regulations can affect the insurance cover you might choose.
  • Apps that can reduce your premiums
  • The three questions you should ask your current provider – today!

You can contact Darren at Darren@proper.insure

Links mentioned in this episode:

Proper Insurance

Noise Aware

Party Squasher

Comet Home

VRS195 – Welcoming Vacation Rental Families in Style with Mary Ostyn

Creating a family-friendly vacation home is challenging, not least because children of different ages have different needs. Unless you have recent experience of vacationing with a lot of kids in tow, how can you really know what is going to make the experience the best possible? Should you provide lots of baby stuff? What types of beds are going to be best for family groups? What safety and liability issues do you need to consider?

These are all questions I asked of Mary Ostyn of Owlhaven.net. With ten children, six grandchildren and several books on the art of bringing up large families, and adoptive parenting, under her belt, she is infinitely qualified to answer them. Add to that a custom-built vacation home in Oregon that was completed and ready for rental just 9 months after breaking ground, and you have expertise in creating, delivering and operating a family friendly rental business unsurpassed by most.

In our conversation, we explore the design of the property, the importance of various aspects of it, and the choices made in marketing and promoting the business.

Mary shares:

  • How to overcome challenges of catering to large families and groups
  • Design features of the home and why they were included
  • Safety considerations when renting to large families
  • What she thinks about teen space, and why it’s smaller than you might imagine
  • Her reasons behind using a property management company
  • Tips for making a vacation home kid-friendly

Links from this episode:

Owlhaven on Bayshore Rentals

Owlhaven website

Woman’s Guide to Raising Large Families by Mary Ostyn

VRS194 – Dynamic Vacation Rental Pricing Explained with Andrew Kitchell of UseWheelHouse.com

Do you adjust your pricing according to the seasons?

I’m sure you do, if as is the case up here in Ontario you have clearly differentiated high and low periods of occupancy.

When demand is super-high and inventory is low you’ll have a much higher rate than at times when there’s a lot of properties available with a much lower demand.

This is the traditional method of pricing and it’s usually coupled with a rough comparison of similar properties in the area – a sort of wet finger approach that’s worked in the past.

But that was when we were all advertising on the old VRBO, and happy with the status quo.

However, now we have significantly more properties on the market and this makes it ever more important to price competitively, and move the rates up and down in accordance with changing criteria.

Andrew Kitchell of Wheelhouse.com joins me to explain how adopting a strategy of dynamic pricing can impact different types of vacation rental owners and increase occupancy levels.

We discuss how to analyse a property to establish it’s unique aspects and how the addition of a simple amenity can make a big difference in occupancy in some areas.

We talk about:

  • How dynamic pricing models are changing the way we present our properties
  • The importance of knowing what guests want the most in your area
  • How rural markets are growing and need to align with practices adopted in urban areas
  • Data science and how it is impacting our industry
  • What you need to know to price your property according to demand
  • How Wheelhouse.com can help owners and managers be more successful at pricing competitively.



VRS193 – Mid Summer Madness – A Diary of A Vacation Rental Property Manager

This week’s solo episode reflects on how this business has changed over the past twenty years, as I deal with numerous issues at properties through the first 6 weeks of the summer.

Back in the good old days we dealt directly with our guests, often took their cash when they arrived, trusted they would clean up before they left, and hoped they’d let us know if something broke down and needed fixing. It was an easier relationship with guests who were far more tolerant and forgiving of human error. They took more responsibility and showed greater self-reliance when things went wrong.

When the power went out, they saw it as an adventure; if something broke they fixed it as best they could and soldiered on until it was repaired; if it rained, they played board games and rummy, and spent hours on jigsaws even when they knew there were pieces missing.

OK – that’s enough of reminiscing the good old times.

Now we deal with a completely different perspective on our rental business and for those of us who have been in the business for a lot of years, we have to be attentive to this and stop bemoaning the changes and begin to recognise we are in a new era of the business of being accommodation providers. We have to stop clinging to the old ways of doing things and embrace new technology, appreciate the expectations of a new market and adapt accordingly, and learn how to market better in an increasingly competitive environment.

I share some of the problems that have been raised this season so far and talk about:

• How we have to deal with increased drama and occasionally group hysteria
• Why an appliance breakdown can lead to a ‘disaster’ scenario
• Power outages and what happens when the wifi goes down
• The importance of an emergency plan – be prepared for every situation
• When guest forget to leave or arrive a day early
• When to be tolerant and the cost of doing this business
• Emergency planning and being proactive
• Why some people should not be in this business
• Tinfoil hat neighbours and coping with the oddballs
• How we are planning for a new season

VRS192 – 10 Sure-fire Ways to Upset Your Guests at Check In

In this solo episode I’m getting back to some basics as I talk about the first 30 minutes your guests experience at your property, and why that is so important to the overall enjoyment of their vacation and to the review they subsequently may write.

There is a magic that accompanies arrival at a vacation rental.  It’s the culmination of months – sometimes years of planning – and all your guests have to go on is the 20 – 30 photos on a listing and the text that attracted them to the property in the first place.

All their expectation have been set, the anticipation and excitement is huge and everything should go according to plan….but so often it doesn’t.  And all it takes is one thing to take the whole group out of their happy place and into another state of mind.

In this episode I explore what can go wrong in the first 30 minutes and how attention to detail and a few little adjustments can make the difference between a successful vacation, and one that is dogged by memories of a poor first impression.

VRS191 – Airbnb Mastery with Eric Moeller

Today’s guest is an investor, home renovator, and Airbnb entrepreneur; the host of the upcoming Airbnb Mastery Summit and founder of Hometel – a luxury property Airbnb management service.

Erics expertise in home renovation and investment is rooted in an early interest in the topic after reading Robert Kiyosaki’s Rich Dad Poor Dad at age 17. From there he went on to score his first mortgage at 19 and renovated his first home while living in the basement. The next two became vacation rentals on the in-demand Jersey shores, and it looked like his future was going to be an easy run….until 2008.

Losing everything in the market crash didn’t deter Eric. In fact, if anything, it fired him up to learn more about investment and to achieve even greater heights, and in 2015 he made his way to San Diego – home of so many startups and entrepreneurs, where his investment portfolio grew. With his eye firmly on the short-term rental market, but ever watchful of the ups and downs of real estate, he founded Hometel, specializing in leasing luxury homes and converting them to profitable short term rentals on Airbnb.

Eric is also the host of the Airbnb Mastery Summit – an online event that brings 20 real estate investors, Airbnb and general vacation rental experts together. Over three days from 11 – 13 August 2017, you can get free access to the event. After that time, the replays and videos will be offered as a package for a reasonable fee. This is a great event full of outstanding information that shouldn’t be missed.

In this episode Eric shares:

  • How his early interest for property investment became a passion for short-term rental and the Airbnb model
  • Why he feels the market is right for buying distressed property, renovating, and posting on Airbnb
  • What an investor should consider when evaluating rural markets
  • The must-have features in all rental homes
  • His views on market saturation
  • The factors owners need to consider when planning an exit strategy
  • Why he founded Homtel and how this works
  • The line-up of speakers for the Airbnb Mastery Summit


Airbnb Mastery Summit



VRS190 – The Vacation Rental Adventures of Travelling Matt Landau – Part Two

Part 2 of the Adventures of Travelling Matt (Landau) takes us to Italy, and Matt’s journey to Rome, the Umbrian town of Guardea and Le Marche in the eastern Italian region of Ancona.

Matt’s telling of the trip takes us to out of the way places and shares his experiences of visiting a renowned silversmith’s workshop, taking a Vespa tour, playing with a local soccer team where he nearly flattened the 70 yr old linesman with an errant kick, and meeting an medley of amazing people along the way.

From Henrietta Kiss, the Hungarian-born owner of Treasure Rome, to Bob and Ian, proprietors of a beautifully restored farmhouse and Debra Haddock whose vacation rental challenges we all share, Matt’s essays draw us into the unique, yet familiar arena of our business, with a European flair.

Throughout the episode, Matt reflects on the similarities that vacation rental owners across the world share and demonstrates how personality, commitment and the drive towards hospitality can make an owner (and a property) stand out.

And just some of the things Matt talks about…

  • How personal passions are the conduit to creating memorable travel experiences for guests
  • The network of locals that create a win-win for guests and the community
  • Why regular discipline of the business needs to be offset by having fun and enjoying life to the full
  • How a host’s personality plays a major role in the success of a business
  • Cultural immersion on steroids while playing with the local soccer team
  • How an entrance to a vacation rental can have a huge impression
  • The magic he experienced with the artisan who made a fisherman’s ring for the Pope.
  • Espresso, chocolate covered hazelnuts, focaccia and plenty of gelato!

And so much more, as Matt reads from some of his wonderful essays on the trip.

Links mentioned in this episode

Treasure Rome – Henrietta Kiss

Casai Dei Fichi – Bob and Ian

Casale Pratto Del Coccinelle – Debra Haddock