How to Build the Perfect STR Message Flow To Boost Guest Experience

Running a short-term rental challenges you to meet guest expectations by being responsive and efficient. 

With so many moving parts, though, it might seem intimidating to tailor your communication to every guest and offer a personalized service—but generic messaging can directly hit your reputation, hampering your guest experience along with it.

If you’re trying to find an easy fix for this challenge, here’s the solution: Automated messaging. Automated message flows make it easy for you to instantly respond to inquiries, greet your guests once the booking is confirmed, answer questions quickly, upsell amenities, and deliver a well-rounded experience. 

This article will walk you through the ideal message flow for a typical STR guest. Stick by until the end to learn how to get an edge over your competitors with one hot tip. 

Guest messaging starts before the booking is confirmed

Before we dive into the essential messages to send every guest, let’s talk about the conversations that happen before the reservation is a done deal. 

Short-term rental guests shop around on booking sites looking for the rental that best fits their needs. Once they come across your listing, they might ask for more information before they’re ready to commit to a booking. 

That’s when you get inquiries like “How fast is your WiFi?”, “Do you have private parking?” or “Can I get a discount if I stay for more than 7 days?”

Responding to these commonly-asked questions in the shortest amount of time possible is key to increasing your conversion rate. Why? Because if you take hours to respond, the guest will have moved on to the next listing and booked with a host who was quicker to get back to them. 

Fortunately, Hospitable.com can automate these responses for you. Our system uses Artificial Intelligence to detect up to 20 different topics that guests often ask about, from “Can I bring my dog with me?” to “Does your rental have Netflix?” and everything in between. This way, you can respond to frequently asked questions within 60 seconds and increase your chances of bagging a reservation. 

Similarly, Hospitable allows you to automate responses to request-to-book and pre-approval messages. What’s more, if you pre-approve a guest and your pre-approval expires within 24 hours, our system sends an automated follow-up to the guest so you don’t miss out on any bookings.  

And now, let’s look at the 8 most important messages to include in your message flow once the booking is confirmed:

8 essential messages to send every STR guest

With automated messaging to do the heavy lifting on your behalf, you can be present for your guests and respond to their needs throughout their booking and stay. Hospitable.com can automate entire conversations for you, so you only have to jump in when you get a super specific question or want to personalize a message to a particular guest.

But why send eight messages when you could just send two or three longer ones? Because you don’t want to overwhelm your guests with too much information in one message. If you do, your guests won’t read the entire message, they’ll miss something important and ask you about it later. 

Instead, send your guests bite-sized information in small, digestible chunks. That way, you’ll give them all the information they need at exactly the moment they need it without bombarding them with messages. 

1. Booking confirmation message

A standard message flow begins with a message confirming a guest’s booking—which is your chance to create a great first impression. 

The first part of this message should thank the guests for choosing to stay at your property. Then you can introduce yourself and talk a little about the property itself. 

The second part of this message should set expectations around what communications your guests will receive. Let them know you’ll send them a message a week before their stay with a guidebook and some local recommendations; another message 3 days before their stay with detailed check-in instructions; and a third message on the morning of check-in with the door code (if you have a smart lock). 

You can also encourage guests to reach out to you if they have any additional questions. 

Lastly, you should ask guests to give you their email address. This will make it much easier to communicate with them in the long run. 

If you automate your booking confirmation message with Hospitable.com, the email address your guest provides will be automatically stored in the guest’s file so you can use it for remarketing purposes later. 

2. Week-before message

The purpose of this message, sent a week before check-in, is to get your guests excited about their trip and provide them with all the information they need in advance.

For example, you can send your guests a digital guidebook with everything they need to know about your property and the surrounding area: recommendations for things to do, a house manual, and a packing list. 

This will reassure guests that you’re expecting them and show that you are an attentive host who wants to help them make the most of their experience.

3. Pre-check-in message

The pre-check-in message should be sent 3 days before the guests’ arrival. This message shares vital details that require special attention, including:

• Check-in times

• Check-in instructions 

• If there is a door code (which you will send on the morning of check-in)

• Directions to the property

• Parking information

• Wi-Fi password and any additional instructions 

• Contact information for the housekeeper

The pre-check-in message is one of the most important messages in the flow because it gives guests everything they need to start and enjoy their stay. 

4. Check-in message

The check-in message should be a quick, short message sent on the morning of arrival that gives the guest the last bit of information they need: The door code.

If you don’t want to give out your WiFi password ahead of time, you may choose to include that in this message as well.

However, be sure not to repeat any of the details you already covered in the pre-check-in message 3 days before. Keep it short and straightforward, and show guests you’re available should they encounter any issues. 

5. First-morning check-up message

Once your guests have settled in and spent the first night of their stay at your rental, you should check in with them. Ask if they found everything as expected and if they need anything from you. 

This is a great way to quickly resolve any issues before they turn into a negative review. Being proactive is always better than staying silent and hoping for the best. 

6. Check-out message

Send your check-out message the night before check-out. This shares the check-out times and check-out instructions, including a list of things your guests should do before leaving, like turning off all the lights, fans, and appliances. 

You can also use the check-out message to ask guests if their stay was pleasant and if they have suggestions for improvements. Lastly, thank them for making a reservation at your property with a note that it was great hosting them.

7. Post-stay message

Your message flow doesn’t end with check-out. Be sure to send a post-stay message, letting your guests know that you’ve left them a 5-star review (which you can automate with Hospitable.com!) and asking them to review their stay in return. 

The best time to send this message is 3 days after checkout, once your guests have already arrived home and had a chance to reflect on their stay. 

You should also see this message as your final opportunity to establish a rapport with your guests so they’re more likely to visit again. Do this by being friendly and appreciative of their stay, and personalize this note to make them feel like they were the ideal guest. 

Maybe you know that your guests were celebrating their wedding anniversary. Take a moment to say that you’re looking forward to hosting them again next year! A little bit of personalization goes a long way toward a memorable experience.

8. Review reminder

Your guests are busy, and it’s only human for them to forget about leaving a review. So, as the final step in your message flow, send them a gentle reminder.

If you’d like to give your guests an extra push, you can explain just how much reviews mean to a small business like yours (not all guests realize the importance of reviews on platforms like Airbnb). And, you can also make them aware of the 14-day deadline to leave a review.

Hospitable.com detects whether the guest has already reviewed their stay and will skip this message in case it’s not needed.

Go above and beyond with these 3 extra messages

You can elevate the guest experience and become a winning host by adding just three optional messages to your message flow.

1. Mid-stay upsell message

A mid-stay upsell message is your chance to add more value for your guests and make their stay extra memorable. 

When you know your guests are enjoying their stay, give them the option to take it to the next level with added amenities and services, like a spa experience or a private chef.

Upsells work best when they’re personalized. Think about what you learned about your guests and the purpose of their trip in the pre-stay communication phase, and tailor your upsells to them. For example, if your guest is traveling with their family, you can offer them childcare services or kid-friendly tours.

With the help of Hospitable.com, you can automatically send upsell messages so you don’t have to lift a finger to earn more from each booking.

2. Early check-in, extended stay, or late check-out message 

If your calendar has some space after the previous or before the next booking, why not offer your guests an extra night’s stay?

You can boost your occupancy and revenue by simply offering guests the option to check in a day early or check out a day late for an additional fee, depending on your availability. 

Hospitable.com simplifies this process by analyzing the availability in your booking calendar for you and automating the extended stay message. 

3. 30-days-later message + marketing email

You don’t want your guests to forget about you once they’ve checked out. On the contrary: You want them to remember their stay and consider booking with you again. 

That’s why it’s smart to send another post-stay message 30 days after checkout. However, don’t just make this an Airbnb or Vrbo message. Pair it with a marketing email sent to the email address provided by your guest. 

This is a great move because it allows you to grab your guest’s attention with the Airbnb/Vrbo message (which they’re more likely to see than your email), and point them towards your email where you can include a discount code. That’s how you win a repeat guest!

Depending on the type of guest you’re hosting and the purpose of their trip, they may not be ready to book again after just 30 days. In that case, it’s a good idea to send a message and a marketing email 180 days after checkout, or 2 months before the one-year anniversary of their stay. 

How to automate your entire STR message flow with Hospitable.com

With so many messages going out with every booking, doing this for multiple guests can be an absolute nightmare. If you’ve already tried and failed at this, you know how challenging guest communication is. 

But automated messaging turns the tables in your favor. Building an automated message flow to communicate with guests at clearly defined moments throughout their stay is seamless with a power-packed platform like Hospitable.com.

Hospitable allows you to set up an array of messaging rules for different kinds of triggers and be there for your guests while minimizing your touchpoints with them. You can maintain a healthy level of interaction with every customer without burning yourself out.

Here’s how:

Step 1: Go to Guest Experience on the left navigation panel. 

Step 2: Start with a template message you want to modify according to your brand. Hospitable offers 7-10 templates to get you started.

Alternatively, you can click the Add New button in the top right corner to create a new message. Choose the message you want to create from a series of prompts and triggers. 

Step 3: Save your messages and you’re good to go! If you have multiple properties, you can create unique messaging rules that only apply to a single property. 

How to personalize your automated messages

You’ve learned how to communicate with short-term rental guests through automated messages. You’ve also set up your message flow on a tool like Hospitable. But now you’re juggling with a more complex problem: “How do I create messages that won’t make me sound like a robot?”

Personalization is the key to making a positive impression on your guests. It’s also critical to building a real connection with them. 

You can personalize your automated message flows with these best practices:

• Use more dynamic content to cover specific details about their stay and add a personal touch (do this using short codes that pull information directly from a guest profile, like name and stay dates). 

• Create an in-depth guest profile with relevant keywords to customize your messages.

• Set up your automation sequence according to the location and timezone.

• Offer a personally curated list of recreational activities and experiences they’d like.

With Hospitable, you can personalize your communications, make guests feel special, and reduce your workload. What’s more, all of this is easy to execute—you can create new templates or edit the existing ones to add interesting details about their stay in a few seconds. 

Hot tip: Embed your brand voice into every single message

We’ve already established that effective communication can make or break your relationship with guests. But one of the most critical and often underrated aspects of memorable communication is maintaining a consistent brand voice. 

As a vacation rental brand, your voice reflects your brand personality through the tone and language you use—be it via social media, email, or in-stay guest communication. 

Keeping this voice consistent wins you customer trust and makes it easy for guests to book their stay with you. This is one reason why brands with a uniform voice across all their channels have seen an increase in revenue by up to 33%. 

So, make sure you clearly define your brand voice, and incorporate it into your guest communication with the right strategy. 

Automate your way into your guests’ hearts 

Automated messaging is an efficient solution to manage guest communications and win back the time you spend answering the same old queries. It also saves you the struggle of constantly checking up on your guests and responding to messages. 

A standard message flow like the one we’ve shared in this guide will show guests you genuinely care and leave them with a fantastic impression of you as a host. 

So, start by analyzing your current guest communication—what questions they ask, concerns they share, or information they need. Then strategize your message flow factoring in all these details. For the final step, use Hospitable to automate the entire flow and get ready to impress your guests!