The Business of Short Term Rentals - What's all the fuss?


Chris is an entrepreneur and the co-founder of Staying Native.  He enjoys riding his bike (pedal kind) and relishes opportunities to share cycling adventures with friends.  On top of that, Chris is generally up for any adventure that provides him with stories to share.  He looks forward to sharing some of those adventures with his sons as they get a little older.

The Rise of the Experiential Traveler

The information available on the internet inspires and supports experiential travelers in their quest to 'Do it like a local'.  These travelers seek to immerse themselves in the cultures they visit, to see how they live and experience their way of life. There are mountains of information available. Reviews and advice on every conceivable component of the trip for the traveler who is willing to invest their time and search out the unique.  Sadly, large amounts information can be both a blessing and a curse.  Not only does it offer fact, but also opposing opinions that make it difficult to decide which reviews and recommendations to believe.

Toronto, Bathurst and Dundas, Crates

Experiencing the local culture at Dundas and Bathurst, Toronto

Rapid Evolution and Competing Agendas

The internet has enabled experiences and business models that weren't possible a number of years ago and suddenly are viable now.  Take, for example, short term rentals.  In the last couple of years, there have been a number of jurisdictions such as New York, Amsterdam, Quebec, and Dubai to name a few that have thrown confusion into the marketplace about the legitimacy of theses accommodations. Such reports cast doubt and cause concern for travelers who want to know that they aren’t at risk if they choose to embed themselves in local culture through a short term rental.

A backyard oasis - Perks of short term rentals

At the heart of the short term rental issue there are a number of competing agendas.  The hotel industry, existing homeowners and neighbours, local businesses competing for tourist dollars, as well as various levels of government which obtain tax revenue through various tourist taxes all have vested interest in short term rentals.  However, the ultimate influencer in the industry is, of course, the traveler, who continues to vote with their wallet.  In the United States alone over $23 billion is spent annually on short term rentals.

Trustworthy and Compliant?

The rate of change in this marketplace has been fast and furious. The main concerns of travelers using these types of accommodations are the ability to trust that the property is as represented and rented legally. Governments globally are playing catch-up with respect to the legalities, and dramatically different solutions are being adopted by various destinations.  Fortunately for the experiential traveler, the debate has begun  and should ultimately lead to solutions that benefit all parties involved.  Main components that we like to see jurisdictions adopt in the legitimization of short term rentals are:

  • Simple and fast registration process for short term rentals
  • Fair fees for property owners/managers
  • Clear rules on tax obligations and
  • Reasonable penalties for infractions.

A window with a view - Overlooking the canal in Amsterdam

Ultimately, it is incumbent upon the traveler to ensure that the place being rented complies with local laws.  We think that the big players (such as Airbnb, Homeaway, Flipkey) should make it easier and perhaps mandatory for property owners and managers to share compliance information, in order to give the traveler further reassurance that the rental property is legit.  There have been instances in places like Amsterdam where travelers have found themselves without a place to stay and without recourse. 

Our advice? Ensure the contract that you sign includes reference to be being compliant and includes the local registration number.  

Advocating for Legitimacy

The US advocacy site was setup by the big players in this industry (Airbnb, Homeaway and Flipkey).   They, along with are others, are advocating on behalf of short term accommodations providers elsewhere.  Their message is simple - to tell people that short term rentals are here to stay so let’s all work together to make them a viable and legal accommodation alternative.

What does it all mean?

The short term rental market continues to evolve for the better as the rules governing this industry are further clarified.  However, during the transition one is likely to hear and read conflicting opinions which will further muddy the waters around the legality of these options. 
Will experiential travelers be deterred?  We don't think so.  After all, it is the experience that makes experiential travellers who they are!  What we advise for now is to do your research before booking and then “do it like a local”.


What are your thoughts about short term rentals?  I would love to hear them.


Short Term Rentals in the News

New York





Short Term Rental Advocacy

blog comments powered by Disqus

Want to share your travel stories and more?

We're looking for authentic travel experiences and local insight into your city to give fellow travelers the inside scoop.

Contact us at