Email Automations: Build Guest Loyalty … and Get Bookings in Your Sleep

Jennifer Perez and Eric Taylor
8/8/2022

Automation is the name of the game for busy vacation rental managers looking to maximize their efficiency. With so many tasks to attend to on an average day, deploying emails to travelers throughout their guest cycle may fall low on the list. However, using your website visitor/guest data and your email marketing platform, you can set up a series of automated sends that not only build guest loyalty and engagement, but also send travelers to the “book now” button with virtually no effort on your part.

After consulting with 14-year vacation rental industry veteran and self-proclaimed “email marketing evangelist,” Eric Taylor (whose formal title is director of email marketing at Bluetent), we’ve put together the following information to help you get started on automated email sends.

We all know that data is the key to any successful marketing campaign, and that certainly holds true for your email marketing efforts. “The guest information data collected during the reservation process is, to me, as an email marketer, pure gold,” Taylor says. “All it takes is relatively simple data, and you can be sending automated emails out constantly, and they are huge drivers of revenue.”

Automated Emails Throughout the Guest Stay Cycle

Prior to Booking

For the details of what to send and when, Taylor outlines the progression using the guest stay cycle, starting with an automated welcome email when a website visitor subscribes to your email list. Welcome emails give you the opportunity to speak directly to travelers who are already interested in hearing from you. “You can set the tone for your new relationship, introduce your brand, and highlight why booking with you is a no-brainer,” Taylor says.

Another automated send triggered very early in the traveler’s journey is the booking abandonment email. Data shows that 68 percent of online shopping carts are abandoned before purchase. Booking abandonment emails allow you to re-engage with visitors who start, but don’t finish, their booking. With subject lines like “Your vacation is just a few clicks away,” these automated sends bring travelers back into the booking funnel.

“Booking abandonment emails have the highest conversion rate of any email we send,” Taylor says. “For instance, they made one vacation rental company more than $25,000 in bookings in just three months.”

Prior to Arrival

There are several automated emails Taylor’s team recommends deploying prior to guests’ arrival. These emails build on the anticipation and excitement that travelers have in the weeks and days prior to check-in. From reservation confirmation emails, to informational guides highlighting details for an optimal stay, to pre-arrival emails with complete check-in information, these messages build trust and confidence in your brand.

In addition, emails sent prior to arrival offer an important opportunity to upsell. Studies have shown that, for every $1,000 a traveler spends on vacation accommodations, they spend $400 on activities and add-ons. “Now is the perfect time to mention anything that will make the guests’ stay better. Travel insurance, early check-in, grocery shopping service, packages, or concierge services,” Taylor says. “Highlight your destination’s quintessential experiences and give your guests the opportunity to book those experiences through a link to your website.”

During the Stay

While guests are enjoying their vacation, Taylor and his team choose to only deploy emails if the message is incredibly compelling. “Some brands are willing to offer a significant percentage discount if guests book their next visit while still on-site,” he says. “Giving guests ‘first dibs’ on property availability before the general public is pretty persuasive.”

After Departure

Getting repeat guests takes infinitely less effort and marketing spend than cultivating new guests, so keeping your brand front of mind with past visitors is a key to success. After the vacation, email marketing becomes your main conduit for keeping your brand in front of travelers. Your automated emails—including review requests, follow-up series (three-month, six-month, etc.), booking anniversaries, and check-in anniversaries—help you maintain a relationship until they are ready to book again.

“I like the six-month email because it has the potential to hit at just the time of year when your past guest is at the ‘peak dreaming’ stage,” Taylor says. “Imagine sitting at your computer during a snowstorm and being reminded of a warm, sunny beach vacation six months ago.”

Taylor’s team advises that, regardless of whether your post-departure emails include a discount, they should always include a link back to your website, leading them back into the booking funnel.

‘Send More Emails’

This amount of interaction sounds like an incredible amount of work, but it’s not. Creating automated emails using reservation data means that, once the campaigns are set up, sends happen without you lifting a finger. Taylor recommends revisiting your email automations on a regular basis—just to keep information current and updated—but other than that, it’s an opportunity to build your brand and revenue for a relatively small investment.

“Our motto is: SEND MORE EMAILS,” Taylor says. “It’s a no-brainer because email marketing garners $44 ROI for every dollar spent.”

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