VRS137 – Lessons From Buying Your First Vacation Rental

“We need another cart” are the words that Gary Miller never wants to hear again.

He also wants to share that there is no such thing as ‘passive income’ in this business because it’s really hard work.

Gary is one of the thousands of new owners who will enter the vacation rental business this year. Some will be lured by the Airbnb concept of shared accommodation, while many will go the traditional route made popular by Home Away and VRBO. Whichever way they go, they will all realize pretty quickly that there are no shortcuts; no easy methods, and no minimal spending once this train leaves the station!

Gary, and fellow new owner Jan Kahlen, have both invested in Ontario waterfront properties this year with the intention of maximizing their income, while still having time to enjoy their properties, and in this episode we explore the world of the start-up owner.

From researching the locations and understanding the different seasonal demographics to making the purchase and starting on the never-ending spend to equip a property, Gary and Jan, share their journey with us.

You’ll learn:

  • How early cottage experiences impacted their motivation to buy a property
  • The research needed to pinpoint the right location
  • Why their properties will meet the needs of the target market
  • What they are doing to capture the market when the high season ends
  • Their favourite purchase
  • Where they found information and education to start off on the right footing
  • Why they are both using property management companies

Serenity Vacation Rentals – Muskoka Pines

CottageLINK Rental Management – Whispering Pines

Vacation Rental Formula

Both Gary Miller and Jan Kahlen are members of the Vacation Rental Formula and regular podcast listeners. They would love you to stop by and ask questions on the start up process so leave your comments below.

Where you can find Gary:






Where you can find Jan:



VRS133 – Getting Ready For My Vacation Rental Season

It’s that time of year again.

The cottage country tradition in Ontario has been part of the culture for generations, and in many areas the families that make the trip have been going to the same cottage for years. Then there’s the new Canadians – our most recently arrived immigrants who learn that the annual vacation to the lake is a rite of passage, and the first visit is often the catalyst to the cottage buying bug that impacts just about every one who experiences it.

Over the years, expectations have risen, and I have the conversation with every new owner about it, and say the same thing over and over. [Read more…]

VRS115 – Association of Vacation Rental Operators and Affiliates (AVROA) with Rod Fitts

I last spoke with today’s guest a year ago and we discussed his passion for the vacation rental industry and the background to his fledgling community organization, the American Vacation Rental Owners Association. At that time, Rod was working on yet another iteration of his website, and although he had a lot of motivation to make it work, there seemed to be a lot of obstacles in the way, notably getting the technical side running smoothly.

Fast forward a year, and with help from some highly respected industry experts, the newly minted Association of Vacation Rental Operators and Affiliates has been launched. [Read more…]

VRS105 – Is Your Vacation Rental Really Family Friendly?

From the early days of vacation rentals, families have found them to be a great alternative to hotels, and all the listing sites tout families as being a prime group to target.

So, why do so many owners fall short of expectations and fail to provide many of the essentials to modern day parents?

Probably because they haven’t been parents for a long time, and things have changed dramatically since the days they used to kick the kids out of the door at the start of the day and tell them not to be late for supper.

Parenting now involves a lot more and if owners are to meet the needs of families with all ages of children, they need to consider what is the new ‘normal’ and get equipped and prepared for them.

Nikki Woodson Blair is a mom to three kids and she has experienced many vacations where a little more attention to detail and an understand of parental (and child) needs would have made a big difference. [Read more…]

VRS089 – Keeping on the Right Side of Your Vacation Rental Neighbours

In this episode Mike and I sit down and chat about two issues that affect every vacation rental owner – neighbour relations and general safety, and discuss the importance of emergency planning.

I brought up the topic of keeping on side with the neighbours because I’m personally affected by super-noisy rental guests next door this week. Fortunately it only happens once a year but it got me thinking how I would feel if our neighbours rented indiscriminately every week of the summer. Then on the other side of the picture, Mike talks about the difficulties he faced with his neighbours at Sea Breeze when he started renting it out and shares his master stoke of genius to get them on side. [Read more…]

VRS086 – 10 Ways to Create a Great First Impression

Each week as the summer goes on, our rental agency deals with myriad issues. Most of them are minor – items left behind, appliances needing repair, requests for early check-in and late check-out etc.

Occasionally, a bigger problem arises like this past week, where an administrative error on our part had a family arriving at a property on Friday to begin their week of vacation, when in fact the owner expected them on Saturday! We had to scramble to find the family a hotel room for the first night and negotiate with the owner for an early check in the following day. Fortunately the guest had a sunny disposition and saw it all as an adventure and she and her family finally checked in on the Saturday for a full week. [Read more…]

VRS077 – 6 Questions Every New Vacation Rental Owner Asks

One of the best parts of my job as a vacation rental manager is to visit new properties, meet enthusiastic owners and talk rentals non-stop. I love to hear their goals for their property and to discuss marketing opportunities for them. On many occasions, I know they have called in other agencies and am always delighted to find they have chosen us over the competition.

Over the years some of the most pressing questions have changed a little but in general they are much the same. Apart from the two most asked questions….

“How much will it rent for and how many weeks am I likely to sell?”

….there are six common concerns that new owners have. [Read more…]

VRS051 – 12 Things That Shouldn’t be Seen in a Vacation Rental

It’s been a while since I had a rant so I guess the time is ripe to get back to basics and list out all those things that give vacation rentals a bad rap.

In my day job as the CEO of a Vacation Rental Management Agency I see a lot of properties. Owners send me photos of the place they want to list, and on occasions they don’t and it becomes a crapshoot. Then I might drive a couple of hours to visit a vacation home that has been described as “luxury”, “executive”, “high end” and just “special”, only to find a weary looking cabin crying out for a makeover and some TLC. The job of telling these owners their beloved cottage doesn’t cut it in the rental market isn’t easy, but it gets done.

I may then see it listed with another less demanding agency, or coming up on a listing site. So I know that some poor unsuspecting family will spend the first few days of their vacation cleaning windows and getting mouse poop out of the back of the food cabinets.

I get it. They love their home on the water; their paradise in the country; the place the family has been loving for years.

Sadly, they don’t get it! [Read more…]

The 10 Habits of Remarkable And Successful Vacation Rental Owners

Over the past ten years in my cottage rental business as well as through this blog and podcast, I have talked at length with hundreds of vacation rental owners, many of whom have been amazingly successful.

Those who have achieved great success share a set of perspectives and beliefs andhabits.


1. Treat their vacation rental as a business and not a hobby

Successful owners talk in terms of a business. They have a marketing strategy, they understand the demographic of their rental guests, and appreciate their role as a provider to the tourism and travel industry. They have great respect for their guests who have selected their property for a vacation and work hard to meet their needs and create guest satisfaction. [Read more…]

Instant Gratification and Other Guest Expectations – How the Vacation Rental Business is Changing

instant_vacation_rental_gratificationA late night phone call on the Friday of a holiday weekend (Canadian Thanksgiving).

An expectation that there would be ‘instant gratification’.

After all, it’s possible to order a pizza, book a flight to San Diego, and speak to a help-desk person in India to deal with a computer issue, so why not book a vacation rental.

What’s the difference?

So, on Friday night when our call centre paged one of our staff to ask him to call back a potential guest looking to book a rental immediately, there was a conflict of expectations.

On our part, we are a small agency covering a huge area with over 10 hours travelling time between our most easternmost and westernmost properties. We rely on our owners or their caretakers to ensure readiness of the properties under their management, but they generally need at least 24 hours notice of a reservation. Even in those properties that we know always maintain a rental-ready status, we can’t guarantee it without a check first.

On the guests part, she wanted accommodation and wanted it now.

In these days of the Book Now button, it should perhaps be easier all round for everyone to be satisfied, but let’s be practical. We are not Holiday Inn’s or Hilton’s that have 24-hour operations, yet vacation rentals are being touted as just as mainstream and therefore, in the perception of prospective guests we should be as accessible.

The expectation of immediacy of booking isn’t the only one that is impacting owners – demands are increasing and it’s worthwhile being aware of how this has come about and recognizing, it’s not about to go away. [Read more…]