Get More Repeat Guests for Your Direct Bookings with Damian Sheridan

Masterclass - Tips and Tricks to get repeat direct bookings

By The Hospitable Team

Have you ever had a guest who loved your short-term rental so much that they couldn’t wait to book again? Well, imagine if every guest felt that way! That’s exactly what Damian Sheridan shared with us during the Hospitable Masterclass on March 2nd.

Damian is a true expert in the short-term rental world and a prominent direct bookings advocate. He offers a wealth of practical and actionable advice, together with like-minded hosts and professionals, at his two absolutely must-attend events – the Book Direct Show and the Scale Rental Show.

So, what can you learn from Damian at our Masterclass? The key to repeated direct bookings is exceptional communication and personalized experiences that keep guests coming back for more. One of the coolest things about the Masterclass was the open Q&A session, where our hosts got to ask Damian anything about his experience with direct bookings and beyond. 

In short, this workshop offered an interactive, fun, and informative session that will leave any host and property manager with actionable insights to apply on daily basis.

Missed the show live? Jump to the bottom of this blog to watch the full recording or buckle up as we bring you the best inspirational highlights below. 

Direct bookings. Why bother?

Damian opened up the discussion, “It’s simple – independence and control!” 

Being in the short-term rental game for over 20 years, before OTAs (online travel agencies) like have got their bite in the hospitality industry, Damian’s learned the ropes firsthand via, as he puts it, “practicing what he preaches.” In his talk, he emphasized that direct bookings give you the freedom to work as you like: from collecting clients’ data and leads to setting your own property rules and payment options. 

“It’s really just the simple freedom to work in a way that you should be allowed to based on the fact that you’re building your own business. You’re not building up someone else’s business! For me, it’s unsustainable to work for one or two behemoths in our industry and it’s something that needs to be changed. And the more people we have behind this movement the better.”

But while today OTAs enjoy a higher level of trust among the “net new guests,” your goal is to build a loyal customer base for further repeat bookings. So, don’t let Airbnb have all the control. How can you do it? Read on. 

Guest Experience and Communication

Damian emphasized that even an amazing website can be hard to convert and statistics report around 80% of STR guests not remembering who we are within 2 months after their stay. That’s why it’s important to “beat the statistics” and ensure your guests remember, especially in the early days. 

“We have to remember that we are accommodation providers. We are not just transactional. OTAs have made it far too easy to see each guest as just a transaction, like a conveyor belt. They come, they leave. Boom. Got the money. Move on to the next one… We have to remember that we’re here to serve their needs, not only thinking about a single transaction. People will be coming back years and years on, and what seemed to be a simple booking can turn into a longer story, if you ensure impeccable service.”

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Social media and Email marketing

Damian highlighted that one of the key factors in ensuring a unique guest experience is effective communication. In social media, being hospitable is essential (pun intended), but it’s important to go beyond simply offering discounts and deals. Share information about your area and showcase things that make your place special. And remember, social media isn’t just about selling; be genuine and connect with your audience.

“It’s not easy and it does take time sometimes if you do it all manually, especially at the early point of your journey. But I think it’s really important to build up your followers on one or two social media platforms and make sure you’re engaging with them consistently. It is fantastic to keep your little community updated, as long as you don’t spam them every day.” 

In terms of other communication channels, consider using email automation to keep in touch with your guests and follow up with them after their stay. As you continue your direct booking journey and scale, it might be worth exploring WhatsApp and SMS messaging as ways to reach out and engage with your guests.

Direct booking website

When it comes to your direct booking website, trust is crucial from the very first glance. Displaying membership in organizations, certifications, and any accreditations, such as local chambers of commerce, can help establish credibility. And don’t forget to update your site regularly with fresh content and use SEO to improve your search engine visibility.

“Show your reviews! And not just copying and pasting, I mean actually embedding them from other sites as a widget on your website. Also… try video testimonials! Ask your guests to record a 30-second video for you, ‘Hey we’re here and we’re having a great time. Damian was fantastic!’ These kinds of reviews resonate so much more than something that’s just copied.”

Finally, make sure your website is easy to navigate and that the booking process is as streamlined as possible. Avoid upselling and focus on creating a seamless experience for your guests. By prioritizing communication and guest experience, you can set yourself apart from the competition and build a loyal following of satisfied customers.

Advertising and Loyalty Programs

While free self-executed promotion efforts can be time-consuming, there are ways to make the most of your budget. Consider advertising via local partnerships with shops, restaurants, and organizations to reach your target audience. Damian also reminded hosts not to overlook Google ads – if you get creative chances are to maximize even a minimum ad budget.

“You can spend a lot of money on things like Google ads and Facebook ads, so I think you have to think quite creatively and beyond mainstream pay-per-click solutions to control your budget. Trust me, there are many ways, that different kinds of channels, that we can use to potentially advertise our properties and get people to come to our websites and book.”

Offering rewards and discounts are a great way to encourage repeat bookings. Hotel chains may have the advantage here with their global memberships, but you can still offer personalized loyalty benefits like early/late check-in or check-out, better service options, and loads of freebies or discounts from local attractions. And remember, a personalized touch can go a long way – reach out and make your guests feel special!

In-depth direct booking overview

Curious to watch the full Masterclass, as Damian Sheridan provides more insights on referral guest traffic, challenges and risks of direct bookings, and driving revenue with property management tools?

Then rush to get the best tips from our renowned industry expert in our Hospitable Masterclass!

Already noted all the details and want to get those direct bookings and repeat guests flowing with even more automated solutions around you? 

Hospitable is here to support a world where short-term hosting is just as carefree as simple property investment. Get your 14-day free trial now! 


Hospitable Masterclasses: STR Tips You Must Know in 2023

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