It's strange CanadaStays is raising funds as a six-year-old company but it will undoubtedly benefit from its partnership with HomeAway and access to that company's Canada rentals.
Without serving a real need of a large sector of the traveling population, it will be difficult to ever truly get many of these startups off the ground.
It's difficult to imagine a single kind of traveler that's underserved in today's market with so many niche services provided online. Despite that, new companies are launched every day to do just that.
It's better to be an early mover in an emerging trend than compete against a dozen or more established companies -- unless you can innovate on others' ideas and emerge with a far superior product.