How to Personalize Experiences While Automating a Vacation Rental Business

personalize while automating

By The Hospitable Team

When a guest books a short-term rental, they’re not looking for a generic Marriott experience: They want a unique, personalized stay that they’ll remember long after their vacation. But customization and personalization becomes increasingly difficult the more you grow.

Automation seems like a potential time-saving solution, but there’s always the concern that a guest will feel like they’re talking to a robot. And what if an automated response doesn’t address what a guest was really asking, making them even more frustrated?

Automation alone isn’t enough. But with the right tools and approach, you can personalize the guest experience while reducing the time you spend on guest communication tasks, making your job easier and your guests happier. 

Automated messages that don’t sound like a robot wrote them.

Customize while automating messages to give guests a more personal experience and help your brand shine through.

Why personalization makes a difference

Personalization takes a stay from enjoyable to unforgettable. It can be a defining feature at every stage of the guest journey, from pre-booking to post-stay. 

Suzanne Hacker, an experienced vacation rental business coach and founder of Welcoming Wow, emphasizes the importance of personalizing the guest experience: 

“As more vacation rentals are owned and managed by larger companies, one great way to stand out is by giving a personal touch, and personalizing communication can help you do that. It’s a good idea to set up templates with whatever guest communication platform you use, and be sure to add your guest’s name to your messages whenever you get the chance.”

Suzanne Hacker, vacation rental business coach at Welcoming Wow

Take a look at a few of the ways personalization can set your business apart: 

  • It helps you build a relationship with your guests. When you get off on a good start with your guests, they’re more likely to treat your property with care, give you a positive review, and become loyal customers.
  • It helps you establish a memorable brand. By using a warm, welcoming, and recognizable tone across your listings and messages, your brand’s personality shines through and helps guests remember you for your future bookings. 
  • It helps you get bookings over the line. Sending a friendly, personalized message when a guest makes a pre-booking inquiry sets a familiar tone that will help them feel more comfortable – and more likely to book.
  • It helps you minimize the fallout of any issues that arise. When there are problems during a guest’s stay, responding with a helpful, personalized response helps ease their frustration and assures them you’re there to help.
  • It helps you get better reviews. Guests will talk about their personalized stay in their reviews. So when a guest feels that they were welcomed and accommodated, they’ll share that information with other guests looking to book your property. 
  • It’s part of the fun of being a great host. This is your business, so your personality should show! Personalizing your messages, even automated ones, makes your job as a host more enjoyable and impactful. 
By being responsive and personalizing their stay, you give your guests an experience they’ll want to repeat.
Source: Airbnb

Personalizing automated messages: 3 essential tools

“Our reviews are constantly talking about: ‘Wow, they got back to me so quickly,’ and say: ‘Josh was such a thorough host.’ What they don’t know is that I wrote those responses four years ago.” 

Josh Strawczynski, short-term rental host

 Personalizing your messages doesn’t have to create more work for you. Because, let’s face it, if this were a manual process, you’d constantly be glued to your phone. 

For example, lets you personalize your guest messages without spending hours a week on communication tasks. Here’s how: 

  • Question auto-detection: Hospitable’s AI can recognize questions about more than twenty common topics and send guests personalized responses instantly. 
  • Canned responses: Sometimes, you want to hit the send button yourself. Canned responses let you prepare common templates in advance and customize them before sending to guests.
  • Shortcodes: These act as information placeholders you can use to customize your message templates with your guests’ personal details.

These tools work together to help you be incredibly responsive to guest questions, before, during, and after their stay, with minimal work. They also form part of your personalized messaging flow that guides your guests through their journey and helps them have the best experience possible. 

Personalized, automated messaging: Here’s how to do it

You may have some reservations about whether automated messages can be truly personalized – and that’s fair. You don’t want your messages to sound like they were written by AI, and you’d hate to send out the WiFi code when your guest was actually reaching out about connectivity issues. 

But there are ways to customize your automated messages and make guests feel like they’re getting a warm, personalized experience. We’re going to cover how you can personalize responses in the pre-booking stage, set up an in-stay message flow, and respond to common in-stay questions, all while automating guest communication. 

How to personalize automated pre-booking inquiry responses

How quickly you respond to guests during the pre-booking process is make or break: Every Airbnb host knows how critical the response rate is to their ranking on the platform and impacts your Superhost status. 

And with millions of other short-term rentals on the market, failing to answer a question quickly could mean a potential guest turns to a competitor to make their booking. But while response time is important, you don’t want to prioritize automation at the expense of personalization. 

The good news is you don’t have to. has a number of templates for common pre-booking situations like new booking inquiries, request to book, and pre-approval for booking. Take a look at the “request to book” template: 

Hello %guest_first_name%, and thanks for your interest in %listing_name%!

I wanted to confirm right away that I have received your request to book my %listing_type% from %check_in%, with %guests% for %nights%. The total price would be %total%.

I will review your request and will come up with an answer as soon as possible so that you can prepare your trip accordingly.


If you need any additional information, please do not hesitate to ask, it would be my pleasure to answer you!

Best regards,


The bolded text in the template above are shortcodes, which can be easily personalized and are automatically populated when a guest makes an inquiry.

You can modify this template even more to make it better align with your brand. For example, you could open the message with, “Just wanted to let you know I’ve seen your booking request,” and you can end the message with “let me know if you have any questions! I’m here to help 🙂.”

Take a look at what the final, personalized message could look like, with the shortcode fields in bold:

Hey Julie, thanks for your interest in our Cozy Cabin in Cabins, West Virginia.

Just wanted to let you know I’ve seen your booking request from October 12, 2023 to October 14, 2023. The total price would be $312.

I’ll review your request as soon as I can and come back to you with an answer ASAP so you can start planning your trip!

In the meantime, let me know if you have any questions! I’m here to help 🙂.

Best regards,


Adding in these warm, personal touches lets you respond to potential guests instantly while maintaining a friendly tone (and sending a message that sounds like a human wrote it).

Create messaging rules that trigger an automatic response to booking inquiries with

How to personalize automated message flow information

Leading up to their check-in date and throughout their stay, there’s a number of messages you need to send to your guests. A pre-arrival welcome message, a first morning message, a mid-stay check-in, and a check-out reminder are all ways you can engage your guests while they’re staying with you. 

But you don’t have to spend time writing out these messages every time a guest books with you. Take a look at this pre-check-in message example template from, which can be a huge time saver: 

Dear %guest_first_name%,

It would be my pleasure to welcome you on %check_in% at %listing_full_address% for your trip in %listing_city%.

Could you please let me know as early as possible at what time you plan on arriving? You are welcome to check-in from %check_in_hour%, any other check-in time would have to be mutually agreed in advance as the %listing_type% may be occupied at that time.


Here are some directions that may help you reach the flat:



I would also like to remind you of the House Rules:


I hope that you will have an enjoyable stay at %listing_name%!

Best regards,


Again, you can personalize this template so it sounds like something you would actually say to your guests. For example, lead in with “we’re excited to welcome you to our listing! What time are you thinking of arriving? Feel free to check in as early as 3:00 p.m. If you want to check in before then, let me know, and we’ll see what we can work out.”

Or take a look at the first-morning message template: 

Hi %guest_first_name%,

We hope that you have settled in alright and that you are enjoying your stay. Please let me know if there is anything you need or if we can assist you in any way!

All the best and enjoy your stay!


All these messages can be customized ahead of time so you can keep in touch with guests throughout their stay and create a thoughtful STR message flow without spending hours a week on guest communication tasks. 

How to personalize common in-stay question responses

You’re probably used to getting a question or two during each guest’s stay, no matter how detailed your house manual is. But you don’t have to respond to each of these messages one by one. 

As we mentioned,’s AI model is able to pick up on over 20 common topics that guests tend to ask about, like WiFi issues and restaurant recommendations. 

But remember that just because a guest is asking about Netflix doesn’t mean they want to know the password. They might be inquiring about some troubleshooting issue, or asking whether they can log into their own account. 

So when editing your templates for automated in-stay responses, you want your answers to cover as many aspects of the topic as possible. For inspiration, take a look at how Hospitable host Jason Wolohan has formulated the answer for questions about the pool at his unit: 

Question topic: Pool

Answer: The community pool is open seasonally from Memorial Day through Labor Day. If the weather is still warm in September the community might leave the pool open a little longer, but this is not guaranteed. The pool is about a quarter mile walk from our cabin. The hours for the pool and the communal fire pit are 10am to 10pm.

Or if you often get messages about the kitchen, take a look at how you can formulate a response that answers multiple questions in one answer: 

Question topic: Kitchen

Answer: If you plan on cooking during your stay, you can find information about how to operate kitchen appliances in the house manual, including video tutorials. That should be enough, but if you’re still unsure about how something works, we’re happy to help. You’ll also find oil, vinegar, and basic condiments in the top right cabinet above the stove—feel free to help yourself!

By personalizing these in-stay responses, you save yourself time and reduce the stress of having to check your phone with every ping just in case it’s a guest asking you something. Meanwhile, guests get a timely, helpful response to their question. 

Help guests resolve issues in an instant without the need to constantly be checking your phone.

Why automated messages are the solution to personalizing the guest experience 

Personalization might not be the first thing that comes to mind when you hear the word automation. But as you can see, customizing your automated responses helps you be highly responsive to guests while speaking to them in your own voice. 

That means no more losing your Saturday morning to responding to guest questions, and no more missed booking opportunities because you got a reservation request at midnight and didn’t see it till the next morning. 

Switching to Hospitable will help you give your guests a smoother, more personable experience while reducing your stress, increasing your bookings, and bringing in more glowing reviews.

Automated messages that don’t sound like a robot wrote them.

Customize while automating messages to give guests a more personal experience and help your brand shine through.

Airbnb Messages: Communication that Builds Rapport

There are some very practical steps you can take to make sure your communication is on point.
So what can you do to build rapport more effectively and improve your chances of getting good communication reviews? Let’s find out, shall we?

Airbnb check-in instructions

Airbnb Check-in Instructions: Tips on How to Delight Your Guests

Your guests’ check-in sets the tone for their entire stay. If this process is stress-free and smooth, it can help lead to positive reviews. Find out how to create check-in instructions for your short-term rental and make the check-in process smooth for you and your guests.

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