10 Sincere Reasons My Friends And I Would Like To Stay At Your Vacation Rental – VRMB
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10 Sincere Reasons My Friends And I Would Like To Stay At Your Vacation Rental

I spent the last few weeks exploring the East and West coasts of the United States, mixing business with pleasure and basically eating too much.

Along with my three best friends from childhood below (who are in medicine, banking, and real estate) we stayed in a handful of vacation rentals, seizing the valuable opportunity to “put myself in the shoes” of the very travelers we work so hard to understand. (Tip: If you have not recently stayed in a vacation rental, I highly recommend this market research. It’s both fun and informative.)


Over the past years, I’ve learned that one cannot improve his or her vacation rental marketing individually – not because the discipline itself is difficult, but because good results in an emerging industry depend on bringing in as many perspectives as possible.

So while my trip brought me dozens of eye-opening vacation rental insights, perhaps the most powerful perspective of all that I can share with you today actually begins with who I am

We Are Millennials, Hear Us Roar

I don’t claim to be an all-around expert on travel or even necessarily marketing. But what I do know is that my friends and I fall into a demographic of traveler that vacation rental owners and managers should try desperately understand.


Because over the next few years, people my age will emerge as the holy grail of the vacation rental business. And if you manage to successfully earn our loyalty now, you may very well have it for life.

Born in 1982, I am of the Millennial generation (anyone born between 1981 and 1996).

Millenials are estimated to be 80 million strong, we spend approximately $600 billion per year, and will comprise roughly 40% of the U.S. workforce by 2020. We are some of your current vacation rental guests, most of your future ones, and we behave drastically different than any generation before us. We hate advertisements, we don’t open emails from people we don’t know, and we consider traveling our birthright.

In short, this is a demographic that all the biggest travel companies in the world are trying to figure out. And I am one of them about to share with you my feelings. Sound interesting? Read on…

How To Reach Millennials

Since many of my readers may only know Millenials as sons or daughters or even grandchildren, I thought it might be helpful to explain some of the ways I found my vacation rental experiences sub-par…as well as some concrete ways you can alleviate those pains in your marketing and secure more bookings from individuals I’ll hesitantly refer to as “my people.”


1. We Are Infovores

When considering a vacation rental in a new destination (for instance, Yosemite National Park), I found myself searching not just for the best property…but for the owner or manager who had the most useful information about the area. In an era of information-inundation, it’s super time consuming to have to scour the web for the best hikes, the tallest waterfalls, and the most likely place to see a bear. I was disappointed to see that very few of my shortlisted properties had their own blog or some cache of useful local information that could come endorsed.

2. We Prefer Off-The-Beaten-Path

On my trip, I found myself pretty much ignoring the vast amount of sterile roadside hotels and motels with their neon signs and massive parking lots. Even in mainstream destinations, my friends and I always sought out accommodations that were on dusty side roads, deep in the wilderness, and generally away from the masses. We like to feel secluded…like we’ve “discovered” a place to stay that few friends or family have stayed at before. For this reason, none of the rentals were “competing” with mainstream hotels in that sense.

3. We Like Bookings Made Quickly

After inquiring to what I thought were suitable vacation rentals for my group, I was flabbergasted by the amount of time that went between correspondences between myself and the majority of the hosts. In the end, the vacation rentals that got our booking were the ones who answered within a few minutes and accepted my credit card or Paypal payment on the spot. In retrospect, I probably booked a few rentals that were less nice than others, based exclusively on the speed at which I could get the booking done and out of the way.

4. We’re Always On The Fly

I need to be able to search for, identify, and book your rental from the convenience of my iPhone, was a thought that came across my mind more than once. Properties with websites that were not mobile friendly made for painful squinting. In one instance, I was gazing out over the most beautiful Santa Barbara sunset as a flock of seagulls flew over the hills when I received an email from one owner asking me to print, sign, and then fax them an attached contract for a stay the following evening. I don’t know why, but this seemed borderline offensive.

53% of millenials would rather lose their sense of smell than their technology1.

5. We Want Insider Access

My friends and I only have a limited amount of days we get to enjoy each other’s company each year. And so the time we do spend in a destination should be maximized…this means avoiding the tourist traps and immersing ourselves straight into the lives of locals (we love cultural nuances). We want to see and do the best stuff in the shortest period of time possible. The owners or managers that won our booking in the end offered something more than just a great property: they offered local contacts like a recommendation to eat at a cutting-edge restaurant in San Francisco or an introduction to the guy who bakes some of the most amazing donuts in the world (Los Angeles). To us, luxury is not 5,000 thread-count sheets. To us, luxury is access. And we were happy to pay extra to get it.

6. We Want Help Making Our Own Decisions

While this may sound paradoxical (yes, we’re complicated), we like to be presented with transparent options from which we can make our own educated decisions. In the case of our rental in Lake Tahoe, the owner actually shared with me the more expensive and less expensive lodging options he recommends in the area. I found this to be confoundingly charming and he won our business. Owners or managers who hoarded information or neglected to offer up alternatives were not helping themselves.

7. We Support Businesses With A Cause

I myself am the proprietor of a gang intervention program in Casco Viejo (Esperanza Social Venture Club) and it is very much part of my identity…so it should be no surprise that I appreciate and gave preference to any owner or manager who commits to a socially conscious component of their vacation rental business. Unfortunately, none of the individuals (of the roughly 20 that I spoke with) seemed to feel this way.

Millenials are considered to be the most culturally and ethnically diverse generation in history2.

8. We Know Good Photos

I read travel magazines, I love travel bloggers, and I follow some of the most absurdly talented Instagrammers on the planet. So I know what good photos look like and I know how easy it is these days to get professional photos done. So I have to say I was really disappointed to see the lack of passion that went into most of the vacation rental photos I was browsing. Some of them looked like Blair Witch Project sets. And oppositely, when I did happen to come across a property with beautiful photos, I was like BOOM! That’s the one! simply because I knew that the owner or manager cared. If you don’t have professional photos of your property, sorry but in my eyes you just don’t care enough.

9. We Appreciate Personality

I think I am accurately reflective of Millenials as a whole in my preference for unusual or interesting personalities. To me, the least intriguing vacation rental options were the ones with short descriptions, no Owner Bio or About Us story, and (my personal pet peeve) lifeless email responses (“Yes we have space. When do you want to arrive?”) While a “Chatty Cathy” may be perceived as unprofessional at a Holiday Inn counter, I love Chatty Cathys! I love the owners or managers who have interesting stories. I love the homes with unique histories. This doesn’t mean you have to give me TMI. But don’t be afraid to align your identity with your vacation rental brand.

10. We’re Not (Too) Judgmental

As someone who has grown up as a young adult with the likes of Yelp and TripAdvisor, I am all about reviews and how “the internet” advocates (or in some cases hates on) your vacation rental experience…so take heed of how you’re acclaimed online. Of course, a traveler these days needs to be weary of scams too. So it wasn’t unusual for me to find a property I liked, then to “Google” it as well as the host to see what others were saying. I was let down by how few owners had any other mentions outside their listing site page! I’m thinking to myself, How can you operate a business charging $350/night for your cabin and not have a website or at least some online equivalent of a business card? Those with few reviews or little/no independent online reputation brought about some suspicion in my eyes.

THE BONUS: Airbnb Rocks!!!

It’s easy to be critical of Airbnb without actively using it. And this trip was actually only the second time I experimented with the platform when looking for a place to stay. Airbnb was great for someone like me because it eliminated a lot of question marks (payment, correspondence, pricing) and made the whole process less difficult: having everything streamlined — from the search to the inquiries to the booking — was a lovely thing! This said, I was torn between wanting to support the owner or manager who was running a mom and pop vacation rental business versus the hosts on Airbnb who appeared (at least in my limited interaction) to be more hobbyists.

Now Is The Time People!

As you can tell, I’m not sharing these thoughts to prove any points or make anyone feel bad (note that I haven’t pointed out any of the properties). This is just the way I (and my friends) like to travel and I thought explaining these characteristics may be useful to non-Millenials.

I came away from these vacation rental stays a bit disappointed in the overall lack of innovation…I felt like most of the owners or managers were still living in the stone ages, advertising only in the proverbial classifieds section and asking me first to print, then to sign and then to fax.

Perhaps it’s because these owners and managers are still catering to bookings of people their own age, who don’t mind (or even prefer) this type of marketing or operations.

But for those who did successfully get my business and who delivered on their promises, I will recommend their rental to anyone I know visiting the area. I’ll brag about it on Facebook. And I’ll likely stay there next year when I visit my friends, or for many years to come with my wife and kids.

(Note: Wife and kids still pending.)

  1. What Millenials Expect From Excellent Customer Service | http://visual.ly/delivering-excellent-customer-service-what-millennials-expect
  2. What Millenials Expect From Excellent Customer Service | http://visual.ly/delivering-excellent-customer-service-what-millennials-expect

About the Author Matt Landau

Matt Landau is the Founder of the VRMB and the Inner Circle, two online resources dedicated to helping vacation rental owners and managers generate more bookings.


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