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When my wife, Kati, and I hit the road in 2014, we had saved enough to travel for a good while, but we knew we’d need another “gig” soon enough. I had my mind set on figuring out something that could be done independently of location.

Our strategy was to book extended stays at vacation rentals for 1-6 months at a time. It was easier to get good discounts that way. But we also liked the idea of staying in one place long enough to get a real feel for it.

Whenever it was time to pick the next destination, I was in charge of researching new options.

I enjoyed it, but there was always inherent frustration because the quality of the offerings was always so uneven. We had to skip countless homes that mayhave been run by great people because their photos were bad or their descriptions unappealing, and we moved on to listings that were more polished…

We’re not picky, so we were pretty sure that if it was bad enough to bug us, it was probably a red flag for the host’s future business prospects. That’s how we began creating a business around teaching all the elements of running a vacation rental.

We ultimately narrowed our focus to just the photographic element of the vacation rental experience, primarily because of Kati’s exceptional talent for explaining how to take great photos in a way that even beginners can grasp quickly.

To skip the story and download the FREE eBook Vacation Rental Jumpstart immediately, click here!

Creating a resource for vacation rental professionals around the world

During these past three years, we never lost sight of the desire for a comprehensive resource that could cover most, if not all, of the critical pieces necessary to be successful.

We’ve pulled together an all-star team of vacation rental experts, covering a wide range of key topics that are germane to winning in the ever more competitive vacation rental landscape, to create our free eBook, Vacation Rental Jumpstart. It’s not the final word, but hopefully, it’s a decent start.

We are extremely pleased to have managed to wrangle more than an hour of undivided attention from 27 of the top minds in the industry. Their specialties vary from software to education, hospitality, regulations and more. We’re proud of both the depth and breadth of what we have been able to include.

I hesitate to summarize the key takeaways from the book because the value of the interviews compiled in the book come from their specificity, rather than any generalizations I can make about them. Like most skills, true proficiency comes from mastering the details. And these experts have been extremely generous in providing the details they believe are necessary to succeed.

Nevertheless, I will list a handful of themes that recurred. This is the equivalent of political analysis, while the book itself is meant to be the nuts and bolts of “how to win a campaign”.

The “bad” news

There are several challenges that exist that weren’t even on the horizon just a few years ago.

Competition has increased substantially

Many locations have three to six times as many listings as they did 36 months ago. To earn what a mediocre listing would have three years ago, you have to be substantially better today, in virtually every way. Period.

Guest expectations have risen dramatically

In a nutshell, guests’ tolerance for substandard hospitality has evaporated. Most travelers have expectations for their vacation rental that are on par with what they expect from a hotel.

The regulatory landscape is shifting rapidly

When it comes to the vacation rental business, it matters greatly where you are in the world. Some locales are embracing it fully. Some are trying to pass draconian laws (and a few have succeeded). It is paramount to research the local regulations on what is allowed wherever you are considering setting up shop.

The “good” news

Despite these few obstacles, the vacation rental industry is looking brighter and more lucrative than ever.

Now there is a path, and there are sherpas

Many of the folks interviewed are pioneers, hacking their way through the internet jungle. The plethora of tools, apps, services, and courses available today is monumental compared to even three years ago. Someone starting today doesn’t even need to make a to-do list – many versions already exist. And everything on the list can be done smoother, faster, or cheaper than in the recent past. Some of the solutions involve automation – of email, of guest access, of calendar synchronization, of evaluating cleanliness – you name it.

But it’s not that the vacation rental industry has become ruled by robots. It’s that tools have been developed to handle the mundane and the routine. There can now be more time available for the personal touch.

Hospitality still matters

The interviews were not primarily about the experts’ businesses. Many of the questions were asked to elicit advice and instruction: “What rookie mistakes do you often see?”; “What would you do differently if you were starting today?”; “What’s one tool/app/service (besides your own) that you would recommend everyone check out?”

But we also asked them about their favorite personal experiences as a vacation rental guest. Their stories often revolved around very small things that made very big differences. Cookies at the end of the day. Connections with hosts that transcended language barriers. A common room that allowed for group bonding in a way that hotel rooms never could.

There was universal recognition that a savvy host, who cares enough to do “the little things” can, and often does, beat out the big guys. Strategizing on how to improve the guest experience and forge a real, trusting relationship with guests is worth the effort. It can be the most potent tool in your arsenal to build a thriving vacation rental business.

What to take away

In over three fantastic years on the road, we’ve become good friends with many of our hosts. Some of them are gaining financial success but at the expense of a decent work/life balance. They don’t have time to research all the amazing new tools and services that have sprung up, many of which could help them grab back a good chunk of their time.

Our fondest wish is that this book finds its way into their hands. They deserve to experience more wonderful and relaxing days. Just like the ones they provide for their guests.

Click here to download the FREE eBook, Vacation Rental Jumpstart!

About the Author

Overlooked 2 Overlooked is a labor of love of two ‘super guests’,  Kati and Brian Greene. After lamenting that 1000s of vacation rental businesses needlessly suffer due to mediocre photos, they created an online training course that lets even novices with smartphones produce professional level images in a matter of hours.

What do you think about this article?

Vacation Rental Jumpstart: The Story Behind the Book
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(2) Comments
  1. David Frankin Reply

    Amazing post.Thanks for the post.Keep sharing.
    https://www.voyagesbooth.com/

  2. Jay Reply

    Great contribution to the VR community.

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