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How To Increase Repeat Bookings From Guests

Repeat bookings – the gold standard for short term rental managers and the hospitality industry. They might seem like a pipe dream from where you’re sitting with your STR, but they are very achievable.

The perks to repeat bookings are endless – not only do they build brand and customer loyalty, but eventually your repeat guests become a passive form of booking out your short term let weeks, even months in advance. But don’t get ahead of yourself here – you need to continue to play an active role in the growth of your holiday rental business if you hope to eventually get to a point where repeat bookings are the ‘new normal’ for your vacation stay.

Today, we’ll explore how to increase repeat customers. Spoiler alert: Touch Stay digital guidebooks check all the boxes as an integral part of your STR toolkit in acquiring repeat bookings!

Why are repeat bookings so important for your short term rental business?


Before we can address how to increase your customer retention, let’s first dive into why they are so important for your short term rental business!

A blue question mark against a pink background

Repeat bookings mean increased chances of guests booking directly with your holiday let, leading to more money reinvested back into your business which would otherwise be allocated to OTA fees. They also boost guest loyalty with new and existing customers, helping you to build your brand and STR reviews.

Not to mention, if a guest has stayed with you previously with no reported issues, they are less likely to report issues when staying with you during future stays, making them a low risk guest to your rental. Let’s dive into a few more reasons why repeat business is vital to the success of your vacation rental business!

Repeat bookings are a fantastic marketing tool


Create an exceptional guest experience and you’ll not only transform your guests into loyal customers but also ambassadors for your business!

A black guest book with gold lettering, accompanied by a hand.

Through positive reviews, and friends and family referrals, a single guest stay can potentially convert into multiple guest stays, increasing revenue, occupancy rates, and guest loyalty for your business.

Your reviews are the gift that keeps on giving, eventually becoming a passive way for you to bring in more guests. Positive guest reviews not only extol the virtues of your fabulous vacation rental for you. They also invite potential new customers to explore more of your property listing, while serving as a fantastic tool to showcase unique touches as part of your guest experience.

On the other hand, reviews can make or break whether a guest decides to stay with you in a heartbeat, which is why we can’t stress enough the importance of adding those glowing reviews to your arsenal!

Repeat bookings increase your customer and brand loyalty


While you’re actively working to collect and compile your polished portfolio of stellar guest reviews and word-of-mouth referrals, you’re building customer and brand loyalty in the process.

a face with a smile on pavement

A brilliant guest experience leads to happy guests who are more than willing to invest, follow, and advocate for your brand. Use this to your advantage! Getting your past and present guests involved in your social media journey not only builds brand loyalty, but also creates a sense of community.

Using interactive features as part of your social media line-up like Instagram reels, polls and reactions, encourages guests to engage with you and your brand and to become part of a bigger movement involving your short term rental.

How to increase repeat bookings from guests


Now that we’ve explored the ‘why’, we’re going to look at the ‘how’. You might be surprised to learn that in order to increase your retention rate of new customers, you need to start at the very beginning of the customer journey.

From the moment your guests spot your property listing and book, to the time your guests return home, your guest experience spans the entire length.

Let’s touch on a few retention strategies you can use to increase your chances of making past guests return to stay with you again and again. These strategies occur at various stages of your guest journey before, during and after they stay with you – apply as you see fit!

1. Enhance your pre-arrival guest communication


Once your guests have booked, now’s the time to kick up your feet and relax until their arrival, right? Wrong! There is so much you could be doing to lay the groundwork for your guests’ stay, and it starts with building out and enhancing your pre-arrival guest communications.

a grey analog telephone on the receiver

Messages sent to guests between their initial reservation and their arrival, equip your guests ahead of time with the resources they need to feel settled, not only in your short term rental, but also while exploring your community.

Now is not the time to drop off the radar for your guests. This only creates confusion on the part of your guests, equaling more questions and concerns for you to address.

Setting up your own guest communication flow is a great way to plan out how you’re going to communicate with each guest. Documenting these flows as templates you can return to for every stage of the guest experience sets you up to provide consistent and concise communication every time.

Or, use Touch Stay’s very own guest alert system Memo, which comes loaded with ready-made templates for you to use. The more messaging you send out, the more efficient your messaging becomes, in turn quickening the pace of your communication flows too.

These sorts of details are of no great expense to you and your holiday let, but they have the potential to add character and leave a great first impression. Combine your smooth booking process with a winning customer experience, and your guests will want to talk about your rental with just about anyone who will listen. It’s about balancing efficiency with human touch!

Your messaging and handling of guests before they arrive demonstrates to visitors that you know exactly what you’re doing, while keeping them engaged. The personal element in your messaging templates also maintains a human-first approach to your communication, ensuring your messaging actually sounds like it came from you and not a robot.

2. Conduct thorough guest research


In addition to planning your pre-arrival guest communication flows, get stuck in conducting thorough research about your guests prior to their arrival. Reviewing your available guest data to understand when and why guests are getting in touch and serving your guests this information as a slice of their pre-arrival communication, can instantly put you in your guests’ good graces.

An individual typing on a laptop keyboard

Additionally, staying up to date with travel trends like sustainability and remote working. Providing suitable accommodation options for these trends, hits the mark for guests needing to work while staying in your short term let, or those looking for more environmentally conscious holiday options.

Gathering specific insights about your guests through your post online booking communication, can also come in handy when it’s time to create a one-of-a-kind guest experience. Is a guest staying with you celebrating their birthday? A wedding anniversary? A honeymoon? Consider leaving a birthday card, a small gift matching their anniversary year, or a bottle of wine for the newlyweds.

Once again, a small personal touch can create a memorable experience and show how you care. Even if they are not staying with you for any particularly special reason, a personalised welcome note, whether handwritten or sent through Memo, can transform your guests’ experience from blah to bling.

3. Provide guests with local resources and hot spots


Peppering your digital guidebook with all of the resources they need to make their stay with you a spectacular one is easy! Guests will appreciate the local guidance on things to eat, see, and do while booked into your short term rental.

A sunset on a beach, a yellow sky with a blue ocean

Local gems, watering holes, and hidden spots your guests won’t find on any Top 10 list, are extra special to add in to your digital guidebook. These might include:

  • A quiet stretch of beach five minutes away from your vacation rental property.
  • An ice cream parlour serving the most delicious sorbet in town.
  • An obscure tiki bar with amazing cocktails.


For guests staying with you during the high season, including specific sections within your digital guidebook about reserving restaurants or attractions well in advance, gives your guests the leg up in making sure they don’t miss out on the sights and sounds around your town.

A personalised notification instructing guests to secure restaurants and tourist attractions, is easy to create and send weeks prior to your guests ever setting foot in your STR.

We recommend sending this message approximately four weeks out, but guests will appreciate that you took the time to touch base ahead of time, to help them plan their itinerary and get the most out of their vacation. And should you have a Michelin star restaurant on your doorstep (or one worthy of such an accolade) that’s reserved months in advance, send this notification sooner!

4. Offer Exclusive Incentives


Providing guests with websites to local tourist attractions or highly rated restaurants in your digital guidebook, takes the legwork out of locating where to reserve their time slot. You can take this one step further, by providing a top-notch discount.

A brick pizza oven with fire inside

Guests love a good deal – partnering up with the popular pizza joint in town creates an opportunity for you to shower guests with discounts, or even your very own affiliate link from which you earn a little kick-back every time your guests dine there. These benefit both your guests as well as your short term holiday let profits.

A reward program is another way to delight your guests during their time with you as well as increase the likelihood of repeat bookings.

Provide repeat guests, as part of your loyalty programme, exclusive access to discounts and incentives. This might look like a small percentage off their next stay, or a gift highlighting local wineries, if they arrange to stay with you for a second or third time. Placing time constraints on these offerings, or advertising them as a limited time offer, increases the sense of urgency for your guests to rebook with you.

5. Continue communication upon guest arrival


When it’s time for guests to arrive, being present and onsite to answer any questions or handle any confusion can save face with exhausted or irritated guests who just want to settle in after their long journey to your short term rental.

hands typing on a mobile phone keyboard

During Touch Stay’s recent webinar “Earn more direct bookings: How to achieve independence from the OTAs”, Katherine Daniel of Little Quarme Cottages revealed that 59% of her direct bookings come from repeat guests.

She emphasised that this is all down to the experience she provides, including supplying guests with her Touch Stay digital guidebook that helps her to communicate effectively and showcase her community.

While online travel agencies make it easy for new guests to review and book your property, transforming the guest experience from the moment guests book with you to the moment they arrive, sets you apart from the competition.

Touch Stay’s Queen of Guest Experience, Tyann Marcink Hammond, sends a text or makes a phone call to her guests right after they arrive, ensuring they settled in okay, arrived safely and to make sure they have everything they need within the house.

By opening this communication line, guests are made aware that as their host, you truly care about them, and are available to take their questions.

6. Follow-up with guests during post-trip communication


Your guests may have departed and said their goodbyes, but that doesn’t mean the communication stops there. Leave a lasting impression that will increase your chances of repeat bookings with your post-trip communication. A simple check in after guests depart to ensure they’ve enjoyed their stay (or even meet them on the premises to see them off) solidifies a memorable experience.

Reach out to your guests with a gentle yet encouraging nudge to leave a review. Better yet, automate this process using one of our handy message templates available on Memo (including requests for reviews) to send to your guests.

People Lying On The Beach

By scheduling one for the day your guests leave, and one for a few days later, this keeps your vacation stay front of mind for your guests, while giving them a few days to settle back into their daily routines post-holiday.

Want a phrase that really pays? Boostly’s Mark Simpson suggests asking your guests “Do you know anyone…?” . This encourages them to reach out to their friends and family who might be on the lookout for a stellar holiday let.

These word-of-mouth referrals are a brilliant hands-off marketing tactic as they encourage a steady stream of high quality, pre-vetted guests. They will be equally wowed by their stay with you as the family member or friend who initially referred them. In turn, asking these guests if they know anyone kicks off the cycle once again and keeps your vacation let top of mind – rinse and repeat!

The final messaging in your post-communications flow reinforces the relationship-building you have completed throughout the entire guest experience. Thank them once again for staying with you and repeat your request for a review or thank them for leaving one already. Point guests to your social media channels so they can follow your short term rental journey and remind guests it pays to stay when they book repeatedly with you, in the form of their discount and/or your loyalty program.

Bottom line, these simple reminders increase the likelihood of them recommending you to their friends and family, and the chances of returning themselves in the near future.

Relish in your repeat bookings with a Touch Stay digital guidebook


Here at Touch Stay,
our digital guidebook templates will have your guests back booking with you in no time! Our templates make it a breeze to include all the practical details your guests could possibly need throughout their stay, while allowing you to add that oh so personal touch as part of your guest experience. Plus, they’ll have access to your personal local recommendations, helping them to truly get the most from your area. Get started with your 14-day free trial today!