As you scale up your airbnb (short term rental) business, look into tools like beyondpricing.com for revenue management and guesty.com for calendar/guest management.

As a matter of fact your transaction does technically meet the time period suggested by at least two court rulings where they attempted to describe an appropriate holding period as two tax years and two calendar years. 

Do you know of a system that the visitors can request a place to stay, when they are approved it will schedule the visit in a calendar and send them a confirmation email?

Keep in mind you could always do a Reverse Exchange which allows you to buy your replacement property first and then you have 180 calendar days to sell your current property.

I started off with Vrbo and Airbnb seems clunky to me.For example it is simple to set your minimum days on Vrbo and this is even displayed on the calendar.

I've been trying to research Ontarios capital gains taxes and it sounds like as long as I live in it during the calendar year as my primary residence I'd be exempt from the tax, so long as it isn't a pattern and the CRA can't say that it was done for income reasons.

@Richard Kapela I would definitely keep an eye on the Atlanta REIA event calendar.

Assume all this happens in less than a calendar year. 

Look on Vrbo and Airbnb and see how full calendars are and what rates they are getting.

But separating the two transactions on the calendar.