How to Stay In Touch With Guests to Encourage Repeat Stays

Another season has come and gone, and you have to think to yourself “my bookings were great, but how can I make them better next year?” That answer is simple: repeat guests. Just because their stay is over, doesn’t mean they won’t want to come back!  We will discuss who to reach out to, what to say when you do reach out, when is the best time to reach out, where can I find the guest contact information, and of course why it is important to reach out to previous guests and encourage repeat stays.

Who are the best guests to reach out to about rebooking?

The easiest way to find who is an ideal guest to reach out to would-be for guests that left positive reviews. When there was a good experience on both ends, the chances of them wanting to rebook your property is pretty great, especially if they take an annual vacation.

What is the best way to stay in touch with previous guests?

We find that emailing a couple times a year is the best way to stay in touch with repeat guests. An email once a week is too much, and only once a year is not enough. You want to reach out enough that they remember your property, but not so much that they find you annoying.

When is the best time to reach out?

You don’t want to wait an entire year to reach out to the guest, because then it might be too late. We suggest splitting it up into 3 time periods:

The Holiday Card:

Whether you want to handwrite this or send out an email, we always suggest sending something around the holidays; this the best time to let them know you are thinking about them, and the end of the year is generally when booking season begins, keeping you fresh in their mind when they plan their next vacation.

The Property Update Email:

Have you made any changes to your property lately? Sending past guests a quick email letting them know about some great changes you have made to your property and also wishing them well is a small step that can lead to a great relationship between you and your guests.

The Rebook Request:

This is an important email to send out. It’s best when sent after already being in touch one or two times throughout the year. You want the rebook request to be sent at just about the same time they booked the year before. We find that a great incentive for rebooking would be to offer them a 10% repeat guest discount. Making it incredibly hard to say no to a repeat stay!

*Reminder: the goal out of all of these communications is to get them to rebook your property, so don’t forget to send them a link reminding them to revisit your beautiful home.

Where can I find the guest’s contact information to send an email?

You can find them in your dashboard if you are using a site like VRBO, or If you are using a property management company, they can reach out to the guests for you! At Gibson Beach Rentals we make sure to be a great advocate for our homeowners doing things like sending monthly emails to previous guests, send gift boxes to guests who leave rave reviews, and even offer repeat guest discounts!

 Why is it important to reach out to previous guests?

It is well known that it is much easier and more cost-effective to rebook a happy guest than having to book a new guest. Not to mention, when you get to know the guests, it’s more comforting to know that you have a relationship with them and they treat your house with more kindness and care. Whether you rent through a property management company or you rent the property by yourself: guests love being in touch with property owners or managers. They can voice their opinions to things they love about the property, and maybe letting you know of some things they would like to see change before they visit again. Either way they get to give you feedback on your home which is great!

As you can see, the importance of reaching out to previous guests can be beneficial to you and the families who have previously stayed at your home. Opening the doors of communication can mean great things for you and your future guests, whether that is a repeat booking or positive feedback. If you would like an email template on what to say to your previous guests, send us an email at:

Published by Tabatha
Monday, September 23, 2019