5 Vacation Rental Experts Look Back on 2015 and Forward to 2016

2015. What a year! From Expedia’s purchase of HomeAway to Airbnb’s $26bn valuation, we’ve seen incredible changes in the vacation rental sector.

We could talk all day about it. But rather than simply waxing lyrical with our own views, we connected with a few industry friends to get their thoughts. And this is no ordinary group of friends… HomeAway’s COO, Airbnb’s Head of Global Vacation Rentals, a startup operator/investor, a former Chief Evangelist, and a fearless vacation rental marketing leader!

We’d like to thank Tom, Brent, Matt, Shaun, and Kirby for being so generous with their time here. In an industry that is running at 100mph we appreciate the moment they carved out to help us!

We asked them all the same two questions:

1. What has been the most exciting change to have happened in the VR industry in 2015?

2. What are you most excited for in 2016?

In last name alphabetical order (no favorites!), here’s what they had to say…

Tom Hale Profile Photo 3Tom Hale | HomeAway

Tom serves as Chief Operating Officer at HomeAway, overseeing all aspects of the product experience on a global basis, including engineering, product management, product marketing and customer experience.

2015’s most exciting change in the vacation rental industry?

Without a doubt, it has to be the day Expedia announced the acquisition of HomeAway as this moment further validated the exploding vacation rental category.  This partnership will accelerate the transition to a world where all vacation rental inventory is bookable online and available as an option alongside traditional travel offerings like flights, hotels, activities, and the like.

What are you most excited about for in 2016?

One of the most exciting trends is the burgeoning VR ecosystem. There is a new crop of companies and entrepreneurs building around big players in the vacation rentals space and this trend is going to go nonlinear in 2016. HomeAway opened up our platform and API to developers in 2015, and I can already see the explosion of new  solutions and innovations that are starting to emerge.

In 2016, HomeAway plans to spend a lot more money to promote vacation rentals and to drive demand for HomeAway partners, owners, and property managers. We’re already the highest ROI channel, and I believe we’re going to supercharge bookings via our family of sites (including vrbo.com) in 2016.  We’re going to do a lot to raise the visibility of the value of professional owners and property managers with a very funny campaign that will put a smile on everyone’s face!

Brent Hieggelke Profile PhotoBrent Hieggelke | Entrepreneur

Brent co-founded Second Porch, the first social channel for vacation homes integrated with Facebook. He sold the company to HomeAway in May 2011. For the last 4 years Brent has been the Chief Evangelist at Urban Airship, a role he left just last week!

Brent has been a good friend and sounding board for the last few years and we’ve had some great discussions over dinner and cocktails about the vacation rental industry, and life outside. Thanks, Brent, for agreeing to participate!



Matt Landau Profile PhotoMatt Landau | VRMB.com

As well as owning Los Cuatro Tulipanes, Matt is the Founder of VRMB.com, a cutting-edge resource in the vacation rental industry, and the co-founder of Esperanza Social Venture Club, a gang re-integration project in the historic district of Casco Viejo.

Matt frequently uses video, both in his blog posts but also in his weekly round-up to the members of his VRMB inner circle. His perspective is always thought-provoking and positive. True to form, he’s provided his response via video, in the same thought-provoking way.



Shaun Stewart Profile Photo 3Shaun Stewart | Airbnb

Shaun is the Head of Global Vacation Rentals at Airbnb, where he oversees the company’s vacation rental strategy and operations. Prior to joining Airbnb in August 2014, Shaun held various senior positions at Jetsetter and Expedia.

2015’s most exciting change in the vacation rental industry?

It’s too hard for me to to pick just one development, so I would point to the overall excitement surrounding the VR industry itself. In 2015, capital investment continued at record levels across a range of VR categories and the OTAs started to make waves in various ways, including the Expedia acquisition of HomeAway and Booking.com’s aggressive launch of Villas.com and their VR focus in general.

The industry is really starting to show the kind of innovation needed to compete on a level with more established travel players like hotels and airlines. As we start to take instant book more seriously, offer in-destination services, create superior experience tools like improved arrival preparation and mobile customer service support – VR is starting to become a world-class travel experience. The flaws that have held the VR world back in the past are fading away and I’m really excited to see what happens in 2016.

What are you most excited about for in 2016?

I truly feel we are watching the development of V2 for VR; a new version that removes the friction from the booking experience and dramatically improves the traveling experience through technology and service. It feels like we have the momentum to make this category of accommodations a leader within the travel industry.

Kirby Winfield Profile PhotoKirby Winfield | Startup Operator & Investor

Kirby built and sold mobile travel startup Dwellable to HomeAway, and before that, launched and sold analytics startup AdXpose to comScore. Kirby provides consultation to investors and startups in the digital advertising and travel categories.

Kirby has always been generous with his time, having racked up hours of phone calls with us over the last year. Thank you Kirby! His generosity continues here, as he brings us a 90-second response to the 2 questions.



2016-12-17T09:38:33+00:00 By |2015 Round Up|1 Comment