Expert Tips on Fostering Guest Loyalty to Maximise Repeat and Direct Bookings

Are you looking for ways to elevate your short-term rental business and secure direct bookings throughout the year to fill up those gaps in your calendar? In that case, you need to know how to attract the right guests, convert them from lookers to bookers and provide exceptional experiences to make them want to book again.  Our inside look at how to attract repeat guests is loaded with industry expertise to help build your strategies for success.

Whether you’re a host with a single property or a property manager with an extensive portfolio, the goal remains the same – to attract guests, accept bookings and build revenue.

However, to be successful, many hosts believe that attracting new guests is the only way to continue to drive traffic to your short-term rental business. This, in fact, can:

  • Take up a large proportion of your time
  • Be costly to you and impact your bottom line

We’re here to debunk the myth that new is always better and show you that there are other ways to build your business and fill those gaps in your calendar. 

Industry Insights

According to AirDNA’s mid-market review of the industry’s performance, although hosts are currently facing economic uncertainty, cost-conscious travellers and an evolving and changing market, the STR industry has defied slowdown predictions. 

We’re seeing travellers:

  • Spend more nights in STRs than ever before
  • Consistent double-demand growth in the last 6 months
  • A shift in demand as traveller interest in shoulder season bookings increases

What does this mean for hosts?

  • Travellers are hunting for value: Despite the economic climate demand is still rife for travel.  
  • A shift in seasonal popularity: Bookings for ‘typical’ quieter months are increasing

However, the current growth of supply, combined with the decrease in occupancy rates, also shows us the industry is flooded with short-term rental options – great for guests, not so much for hosts – and with hotels now inching their way into the short-term rental space, the market is even more competitive than before. 

Travel consumers (potential guests) have to scroll through a multitude of options before making a booking decision. 

So, what are you doing as a host to combat this?

Attention-grabbing imagery? Well-written listing descriptions? These are all great to help grab the attention of new guests, but what about guests who have already stayed with you? 

Are your efforts targeted towards attracting them to book again? If not, fear not!  

We’ve interviewed 6 industry experts to highlight the importance of direct bookings and all the ways you can foster guest loyalty and captivate your guests for endless return visits. 

Who we asked:

According to Airbnb Coach Tatianna, many hosts commonly ask about direct bookings and the opportunities they bring. 

We will answer these questions through insights shared by our following industry experts:

Andrew Schorr

Director of Product at Hospitable

Attention to detail when communicating with your guests can really allow you to stand out from other hosts.

Book Direct Founder

Arthur Colker

Founder and CEO of StayFi

“The best place to start with direct bookings is by marketing to individuals who already trust your brand.”

Book Direct Founder

Damian Sheridan

Founder of The Book Direct Show and Scale Rentals

“Communication is key. Keep in touch. Be authentic. Be the local expert. Be passionate. Be real.”

Kelly Odor

Marketing Director at Bookster

“Attracting direct bookings needs two aspects to be present; having the right tools, and having the right knowledge”

Boostly CEO

Mark Simpson

Founder and CEO of Boostly

“Your website should sell your unique offerings from the offset and ooze your brand from every corner.”

Tatianna Taylor-Tate

Short-Term Rental Coach

“Find unique ways to set yourself apart while making the guests feel special.”

Ready to convert your guests into repeat bookers and reap the benefits they bring? 

The ideal percentage of direct bookings vs third-party bookings

For property managers and hosts, measuring your performance of bookings will not be a one size fits all. 

Given the dominance of OTAs (Airbnb, Vrbo,, Expedia) in the short-term rental market, aspiring for 100% direct bookings is overly-optimistic and may bring challenges, especially when first starting in the industry. 

Therefore, the ideal percentage of direct bookings, in comparison to third-party bookings, will depend on your distribution strategy and goals as a property manager. 

Our experts said:

“There is no right or wrong answer here. Any STR host/manager who is looking to generate more direct bookings can look at increasing numbers in very modest milestones. If that’s going from 0% to 1%, that’s fine. It’s what is right for you given your time and talent resources.

However, there are certain things that we should all be analysing when addressing the goal of increasing direct bookings:

  • What is your current cost of acquiring direct bookings (think about your time, SEO, and paid advertising budgets)? This may be costing you more than you might think.
  • Is the lack of data alongside your OTA bookings costing you your communication and relationship with guests?
  • Are you over-compromising on your T&Cs (e.g. cancellation policy, deposits, payment terms)? 
  • Are you reliant on 2/3 booking channels for the majority of your bookings? If so, what happens if your listings get pulled overnight without any reason or explanation? (It happens!)”

Damian Sheridan, The Book Direct Show.

“We’re advocates of using third-party OTAs to list your own property, especially if you are just starting out and do not have your own captive audience of new or repeat bookers just yet.

As you grow your business, it’s great to see your calendar expand with direct bookings vs third-party, as it means you are becoming less reliant on the search algorithms of those third parties.

Andrew Schorr, Hospitable

“This is entirely down to the strategy of the property managers and hosts. Some property managers want to attract 100% direct. This can be for a variety of reasons; from reducing channel fees, maintaining control of booking and cancellation terms and conditions, wanting to build their brand, to an outright dislike of the channels.”

Kelly Odor, Bookster

Happy Guests

The benefits of direct bookings and repeat guests

Listing on multiple channels is a great way to help attract guests to your property, but what if they’ve already stayed with you? How are you ensuring these guests don’t just forget you after their stay? 

Building a direct booking strategy can in fact help you nurture current and past guests which will help secure repeat bookings and fill those gaps in your calendar. 

The benefits of direct repeat bookings include:

  • Increase your direct booking performance percentage: Guests are more likely to book direct than through a third-party channel if they have had a previous booking with you where you have gone above and beyond in meeting guest expectations.
  • Reduce third-party channel and booking fees: Say goodbye to paying fees for every booking you receive when you go direct. 
  • Build your brand and reputation: The more guests book again, the more memorable you are to them, which includes your branding and your reputation – don’t forget, consumers are 90% more likely to trust brands recommended by friends.

So, when do hosts typically turn to direct bookings?

“Hosts with 1-5 units who have overcome the early daunting obstacles like creating their own website, forming a company, taking deposits and payments and the risk of unknown guests, are usually ready to explore the many ways to generate direct bookings. 

This usually speeds up at the point when the business becomes full-time.”

– Damian Sheridan, The Book Direct Show

It’s useful to know when the shift towards direct bookings occurred. In the past few years, we can see that the Covid pandemic has had a huge impact on this. 

Covid was clearly the seismic catalyst for many hosts around the world to begin exploring direct booking strategies. When several of the major OTAs were effectively closed for business (and enforcing cancellation refunds) many property managers who relied exclusively on them were left without any paths to revenue.”

Damian Sheridan, The Book Direct Show

Attracting repeat guests

Using your direct booking website to attract repeat guests 

Repeat guests will typically skip the middle man (the OTAs) and come straight to your direct booking website when looking to make their next online booking. It’s important to ensure you make your website easy to use, with a simple booking process and attention-grabbing media to ultimately secure that repeat booking.

Mark Simpson, CEO of Boostly said, “Your website content is a great way to connect with previous, potential and current guests. A regularly updated blog targeting specific keywords will do wonders for your SEO, but it also provides interesting content for guests to read too. At Boostly, we’ve recently integrated ChatGPT into our direct booking sites, so hosts can create unique optimised content for their site at a click of a button.

Remember, your booking engine should be easy-to-use and display real-time pricing and availability – the last thing you want is a guest jumping through all the hoops only to be met with ‘Sorry, these dates aren’t available ”

It’s important to build trust with your direct bookings. Guests won’t book direct when they don’t feel comfortable with your brand or website. 

“We believe that the best place to start with direct bookings is by marketing to individuals who already trust your brand and have stayed with you before. In StayFi’s case, guests are always providing this data when they log into the WiFi, and they are opting in for a vacation rental operator’s email marketing program”

Arthur Colker, StayFi

Here are some of the key areas property managers and hosts should focus on to help build a website that converts:

  • High-quality imagery: including every room and a detailed property description. Give them everything they need at their fingertips
  • A clear homepage: showcase your best properties to really grab their attention. Their top properties for a reason.
  • FAQ page: cover all the frequently asked questions, this will save you and your guests time. You can even include a chatbot feature should they want to know more.
  • Contact details: Make it easy for your guests to reach out. Communication is key in building and retaining relationships with guests.
  • Trust: Create company about pages to show a human side to the business and ensure your website uses SSL encryption to help enforce the legitimacy of your website and prevent website fraud. 
Repeat Guests

The importance of targeting guests that have already stayed at your vacation rental

Converting a guest to book again directly will be easier if they have had an exceptional experience, in comparison to someone who is unfamiliar with your brand/company or had a sub-par experience. 

“One issue in the vacation rental industry is that guests have a great deal of trust in the OTAs, but may never have booked directly with an operator before. Once the guest stays with you, we can eliminate the missing trust factor and, if marketed to properly, the guest will be much more likely to book again directly.”

– Arthur Colker, StayFi 

Are repeat guests risk-free bookings?

“Repeat guests can offer you greater reassurances as you have already previously hosted them. However, this does not mean their booking is risk-free! Guest screening and other risk management measures should always be undertaken with every booking. Remember, accidents can happen, and it’s better to be prepared than out of pocket or even closed down.”

Leo Walton, Know Your Guest by Superhog

Using comprehensive guest screening measures to mitigate the risks of fraudulent bookings, parties, damage and even illicit activities, is essential for every booking, no matter what channel they have come from. 

“Considering fraud alone, in most cases, yes, we could assume the risk decreases. However, even if the person making the booking is the same, the nature of the trip and the guests travelling with them could be different. A guest whose first trip to your property was on business and travelling alone is much different than when they return for a weekend with a bunch of friends.” 

– Andrew Schorr, Hospitable

The risk is a lot lower if the guest is a repeat guest. However, for the safety and security of your property and future guests, you always want to ensure you have a strong verification or screening process, just in case.”

Tatianna Tate, Short-Term Rental Coach

Start screening your guests and protecting your properties today

Utilising your direct booking risk management strategy

It’s always important to ensure you have the right risk management strategy in place. After all, your property is a large investment. 

A risk management strategy is extremely important when building your direct booking strategy. In order to protect your direct booking business and property you want to have a strategy in place to firstly prevent risky bookings and ultimately, be there in case any issues were to arise.  

This can include:

  • Clearly stating your cancellation and refund policy
  • Securing the correct insurance coverage for your properties 
  • Having a strong guest screening process for new bookings or enquiries.”

– Tatianna Tate, Airbnb Coach

Know Your Guest CTA

Creating opportunities for repeat and direct bookings 

As a property manager or host, the growing circulation of short-term rental technology means it is more important than ever to start streamlining your operations. 

Property management software providers can help you do just that, with integrations with all key short-term rental tech companies. 

Not only that, but a PMS can, in fact, help you build your direct bookings and increase your repeat booking performance.

“Hosts using Hospitable’s Direct Premium features get to keep full control of their bookings and the way they market their properties, but we’re lightening the load by taking administrative hassles and many of the risks associated with direct bookings off of their plates. Premium is a unique offering in the marketplace that is a hybrid of the good things OTAs do, combined with the freedom and cost savings of direct bookings and it is also supported by our core time-saving features that allow you to automate guest messaging, schedule tasks for your team, and avoid double bookings with a centralised calendar.”

– Andrew Schorr, Hospitable

“Attracting direct bookings is not just about having the right tools. It’s the knowledge behind the process. It’s about understanding where guests come from, how to attract new guests, how to encourage repeat bookers, and how to improve the guest experience to boost referrals, and for that, Bookster provides education and training covering a range of topics and the latest insights.”

– Kelly Odor, Bookster

So, how important is email marketing when optimising your conversion of guests to repeat bookers?

“Without some branded post-stay touch points, guests will not remember your brand when starting the planning process of their next trip.”

– Arthur Colker, StayFi

“Email marketing has to be done carefully, and for those with guests from Europe and the UK, following GDPR regulations. 

Following the departure of the guest, a follow-up email is essential to thank the guest for booking with them, ask for a review and to promote the opportunity to book again directly. 

Those who have signed up for email marketing should continue to get regular, but not too frequent emails, with reasons to come back: whether that’s special offers, exciting events nearby or top attractions of the area.”

– Kelly Odor, Bookster

To help you stay ahead of the competition and deliver great guest experiences each and every time, check out our ultimate A-Z guide on how to have good guests by being a great host. 

6 tips you can use to help convert guests to repeat and direct bookers

  1. The guest experience: Look at the journey a guest goes through, from the moment they find your home and book, to the time that they return home. Be warm, welcoming and accommodating at every stage. If you know a child is staying or even a pet, leave little extras that will make their stay more comfortable. It really can be the little things that make all the difference.
  1. Email marketing: Use short-term rental technology to capture email addresses from your guests and add them to marketing campaigns in Mailchimp or other email marketing software. A good email marketing strategy will automate emails so that you don’t have to worry about sending them – but you can easily track who has clicked through and booked as a result. 
  1. Multiple brand touchpoints before, during and after the stay: Reinforce your brand identity throughout the whole guest journey, including your website, social media, communication and in-home branded items (fridge magnets, coasters etc).
  1. Loyalty programs: Offering exclusive benefits such as discounts, free upgrades, priority services, or other perks, loyalty programs create a sense of value and encourage guests to book again to take advantage of these rewards. For example, properties can provide extra rewards or discounts for guests who book multiple times within a specific period or reach certain milestones in their loyalty journey.
  1. Stay active and up-to-date marketing your property on social media: Focus on growing an engaged community either through socials or community groups. Offer giveaway opportunities (the chance to win a free night etc) to help build social branding, reshares, reviews and your own community.
  1. Communicate regularly with guests: Explore the potential of a Whatsapp business profile to engage with those in the ‘dreaming’ stage of their next holiday.

Are you ready to debunk common direct booking myths? Sign up to our exclusive webinar including our 6 industry experts, today!

6 reasons why a guest won’t become a repeat booker

  1. Poor guest experience: The most common reason a guest won’t convert to a repeat booking is because of an average or poor experience. Travellers and guests want value for money – and they certainly don’t want to pay again for poor service.
  1. No communication post-stay: If you’re trying to manually keep in touch with your guests before, during and after their stay, it’s going to be difficult to be super helpful and super responsive all the time – especially if you’re managing multiple properties at a time. Messaging automation and AI tools can help you keep your communication to a high standard.
  1. Lack of cleanliness: A missed clean can really set you back. Ensure you’re utilising automated calendar scheduling with your short-term rental cleaners through a PMS, to not miss a clean.
  1. Not visiting the area again: Sometimes, it is as simple as the guest not looking to visit the location again, rather than you missing the mark.
  1. Lack of competitive advantage over others in the market, including OTAs and similar listings: This includes your pricing, availability, location and even amenities
  1. No optimised direct booking website: Make it as easy as possible for guests to book on your website, but make it secure. Guests need to feel secure when booking online. Are you telling your website visitors how their payments are completely safe? 

Know how to track your repeat booking KPIs

Finally, if you are looking to increase your repeat bookings, you’ll want to look into your conversion rate KPI. This will help you measure, monitor and manage your repeat booking performance. 

So, how do you track your conversion of guests to repeat bookers?

“You can create unique coupon codes and ask guests to use these when booking another stay. This is one of the easiest ways to track the conversion KPI of quests to repeat bookers. A coupon code field can easily be added to a booking system and property managers can easily view the number of guests who have redeemed a certain coupon code – from here, they can identify trends, patterns, and insights related to guest behaviour and repeat bookings.”

– Mark Simpson, Boostly

By not tracking your repeat booking performance, how will you know what is working and what isn’t?  You can also potentially miss out on great opportunities that can help:

  • Build revenue
  • Fill gaps in your calendar
  • Build company reviews and reputation
  • Build independence away from OTAs

So, are you ready for safer bookings and more independence as a host?

Get started with the leading risk management platform and start protecting your repeat bookings today!

Speak to us today!

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