How Airbnb and Uber are transforming the modern vacation

Airbnb isn’t just a less expensive alternative to a hotel—it’s a subtly different kind of travel experience

Airstream trailer in a field near Portland


A few months ago, my wife and I were looking to book hotels for our upcoming vacation to the Western U.S., and we were dismayed. Seattle and Portland were two of our key stops and we couldn’t find anything decent for less than $300 a night.

Our trip was going to take us to Montana and Wyoming and eventually down into Idaho as well. We were shocked when hotels in Boise were similarly expensive. How the heck does Boise have the sort of demand to justify such prices?

We decided to give Airbnb a try. Neither of us had ever used the accommodation-sharing service before. It has felt a little sophomoric to me, like something I would have been into in my 20s, but not now as a supposedly sophisticated adult. (Why yes, I do still play with Lego – why do you ask?)

Our interest was piqued as we browsed at the comparative prices of listings, as well as by the photos and descriptions of many of the places. Oh look – here’s a treehouse we can stay in! Wow, an Airstream trailer – wouldn’t it be neat to sleep in one of those?

We booked an apartment in downtown Seattle (grand total: $160 a night), a studio attached to a garage in Columbia Falls, Montana ($125 a night) and an amazing-looking king suite in a forested house in the hills of Portland ($105 a night).

The process was painless and in each case, the proprietors were quick and friendly with their responses. Still, despite the simplicity and the obvious savings, we were a little hesitant about whether we were doing the right thing.

Once in Seattle, we called the number our host provided. No answer – uh oh. We started to wonder if it had all been too good to be true. Everyone has heard horror stories about Airbnb’ers getting stiffed by unscrupulous hosts. Were we about to become another anecdote?

We ended up getting into the building the old-fashioned way – we snuck in behind someone else – and headed to the apartment. Sure enough, the keys were under the doormat, right where the host said they’d be. A few minutes later, we got a text from the host, who apologized. He was in the shower when we called. Crisis averted.

Upon entering, we encountered a couple from California. They were renting another room in the apartment and were making their way up to Vancouver. We swapped travel tales, shared some tips and were on our way. Otherwise, we never saw them again.

Aside from the arrival hiccup, our stay was perfect. The room itself had everything we needed: private bathroom, comfy bed, a fridge to store food and drinks. I was exceptionally happy with the wi-fi – I’ve written several times about how universally bad it is at hotels, so having a decent connection was a refreshing change.

As an added bonus, our hosts had Hulu and Amazon Video hooked up on the TV. As a culturally protected Canadian suffering behind the oppressive wall of telecom company streaming rights, these are services I don’t get to experience regularly.

Our stay in Montana was similarly great. We actually met our hosts and they shared tips about good places to eat nearby. We played with their dogs and chatted about life in Montana. They even did our laundry. And the wi-fi was good.

With a couple solid experiences under our belt, we felt confident enough to expand our Airbnb horizons. We booked a place in Gardiner, Montana, right at the entrance to Yellowstone National Park. We had intended to camp in the park itself, but the forecasts of near-freezing temperatures had us worried since we hadn’t properly prepared.

The room came to $110 a night and the proprietor was an amazing woman who worked for the park. Naturally, she was full of useful information about Yellowstone and was happy to loan us books, her binoculars and some camping chairs. She even baked us cookies and yes, the wi-fi was great. It was fast enough to stream Netflix at night.

We also booked in Boise ($110 for one night), a fantastic house in the hills overlooking the city. We had a room on the bottom floor, complete with coffee and snacks in the morning. The views of the city – and the sunset – were magnificent. So was the wi-fi. The bathroom even had single-use bars of soap and shampoo.

Our trip ended in Portland at an incredible house that can only be described as a mansion. We luxuriated in an uber-comfortable king-size bed and took reading breaks on couches in the nearby study as a water fountain babbled peacefully in the background.

Our friendly hosts greeted us cheerfully and asked if we needed anything. We didn’t – they had thought of everything. The house itself, meanwhile, was situated on a hill amid Portland’s lush forests. It was idyllic, peaceful and the perfect place to end a vacation.

All told, we had nothing but good – even great – experiences with our Airbnb bookings, to the point where we wondered why we’d ever want to stay in a hotel again. A bad experience or two are inevitable down the road, but we’ve had plenty of those in hotels too.

The wi-fi situation alone is enough to get me to switch permanently. Airbnb hosts have to provide good connectivity, not just because their guests expect it, but because they usually have to use it themselves.

Hotel operators should similarly be made to live with the wi-fi they’re providing as a condition of their operating licence.

It’s worth mentioning that Uber played a key role in our vacation as well. The experience was also potentially transformative.

The 20-minute Uber taxi ride to the airport in Toronto cost us $45. In Seattle, a similar ride cost $8. The exasperating difference really highlighted the competitive problem we have at home.

Uber isn’t available in official Portland taxis, so we opted to give the much-maligned UberX a try. UberX allows anyone to become their own taxi service, provided they can pass a background check with the company and their vehicle meets certain standards.

As with Airbnb, we had never tried UberX before and were a bit nervous because of the horror stories. Passengers have apparently been insulted, robbed or even raped. With such tales circulating, how could anyone not be wary?

Our trepidation was misplaced, at least with the two rides we took. In both cases, the drivers were friendly, polite and engaging. Their cars were new and spotless. Most importantly, the 20-minute rides to our mansion in the hills cost about $13 each time.

We thought back to how much we paid in Toronto and wept. Something needs to change back home, and if it takes Uber to do it, then so be it.

Airbnb and Uber are at the vanguard of the so-called “sharing economy,” although a more accurate description of what they do might be person-to-person services. A big company is taking a slice at the top, but both services essentially allow individuals to connect with each other and keep the lion’s share of the money being exchanged.

For the most part, the virtual absence of a middle man – as well as greed by bigger companies for higher profits – is what allows for prices to be so much lower than the official competition’s. And it’s what has those competitors so angry.

Both Airbnb and Uber are at the centre of a veritable public policy maelstrom right now, given how they’re shaking up the incumbent system. Airbnb is being accused of contributing to real estate woes in several cities, as hosts take valuable inventory and rent it out. Uber, meanwhile, is taking flak for enabling unlicensed drivers to take money away from those who are playing by the rules.

The thing is, all of the Airbnb hosts we spoke with had nothing but praise for the service. The two drivers we rode with also love UberX – both said they make more money with it than through their day jobs (one was a teacher).

That’s a small, subjective sampling of opinion, but given the skyrocketing growth rates of both companies, it’s probably representative of the larger whole as far as service providers go.

If our outstanding experiences on the consumer’s side are similarly representative of the larger whole, well then it’s pretty clear the so-called sharing economy is here to stay.