How to Boost Vacation Rental Bookings with Repeat Guests

Mar 15 2023

Get tips on how to use Hostfully to optimize your vacation rental business and make more profit.


What’s in this article?

There’s a widely accepted rule in business that it costs more to attract a new customer than it does to retain one. The same goes in the vacation rental industry: Repeat guests can be a reliable source of reservations and help you fill in those pesky gaps in your booking calendar. 

But aside from providing a memorable stay, how can you get your guests to book with you again? We’re here to walk you through tips for:

  • Why it’s so important to attract repeat guests to vacation rentals
  • How and when to contact your past guests 
  • How to attract guests back to your properties

So follow these recommendations on bringing guests back to your vacation rental for improved booking rates and increased revenue.

CTA for repeat guests

Why should you attract repeat guests to your vacation rental?

The value of getting direct bookings for your vacation rental is clear: You don’t have to pay OTA fees, and you have more control over how you do business. But an especially important part of direct bookings is your repeat guests. 

Hostfully’s 2022 Vacation Rental Industry & Hospitality Report found that the bigger property management companies grow, the more important direct bookings become. By focusing on the marketing strategies, quality of service, and relationship building that contribute to gaining more repeat guests, the less reliant they are on third-party platforms.

“With the increase in competition and the potential for demand to slow, it’s no longer an option to sit back and let the OTAs do it all. A proactive strategy to build a brand, develop content, and communicate effectively with potential and booked guests will be necessary to create a better guest experience and drive repeat bookings.”

-Heather Bayer, Training Director at Vacation Rental Formula

With the right approach, every guest that books again with you will do so through your direct booking website rather than through an OTA. 

This gives you instant financial benefits, but bringing back repeat guests also makes your job that bit easier. You already know the guest likes your property (that’s why they’ve booked again, after all), which reduces some of the stress and pressure of trying to meet their expectations.

Diagram showing the relationship between direct and repeat bookings.
Ideally, repeat bookings will make up a significant portion of your direct bookings. And even more ideally, all your repeat bookings will be direct.

How and when to contact your past guests

As we’ve said, getting repeat bookings is an important strategy. But blindly contacting all your guests to tell them to book again will give you a lot of work with a low success rate. So here’s which guests you should contact, how often to reach out, and what you should share with them. 

Which past guests to contact

Should you reach out to all your former guests? Are there any guests you should leave off your email lists?

Suzanne Hacker, a vacation rental coach and founder of Welcoming Wow, states that “all previous guests should be put into your email marketing campaigns, unless they were problematic. You can easily remove a guest from your outreach efforts if you had an issue with them.”

This applies both to guests you left a review for and guests that left a bad review for you. Go back through your reviews and note down these guests to remove from your marketing campaigns. 

If you had a bad experience with a guest, reaching out to them with repeat booking discounts probably won’t mend the relationship. Let them go and focus on other guests that are happy to visit your property again. 

How often to contact past guests

Suzanne says “there are no set rules” when it comes to how often to contact past guests. But you don’t want to be just another email spamming their inbox, so keep your messages thoughtful and well-timed. 

Reaching out to guests two or three times a year is a good benchmark. And pay special attention to when a guest’s last booking was: If they stayed with you in December, send them an email a couple of months before, in October the following year, to remind them of your vacation rental if they plan on visiting the area again.

Suzanne emphasizes that “you can also reach out to guests when you want to run a special or have openings in your booking calendar.” Repeat guests are an excellent resource for filling in those awkward gaps between reservations: Send out a last-minute booking discount to former guests to maximize your occupancy rates. 

What updates to share

Aside from last-minute booking deals, there are a few updates you can share with former guests to pique their interest in rebooking with you:

  • Property updates and renovations: Installing a hot tub or creating a game room gives you the perfect reason to reach out to past guests. Send out an email when you make updates or renovations to your short-term rental, and be sure to include pictures that grab their attention.  
  • Local events: Are there any local festivals, sporting events, or special occasions happening in your area? Reach out to guests a month or two beforehand to let them know about the event and remind them to book with you if they plan on a visit. 
  • Special discounts: As we mentioned, you can reach out to your guests with last-minute discounts to fill your booking calendar. But that’s not the only reason to send a coupon code—this can help you get more reservations during your off-season as well. 

How to attract more repeat guests to your short-term rental

Now that you know the “why” behind getting repeat guests, it’s time to look at the “how.” We’ve compiled practical recommendations for getting more guests to book again with you, from how you can capture guests’ information to how to make them want to come back time and time again.

It all starts with the first booking

The first booking is your chance to shine and make your property stand out in your guests’ minds. But this is also your chance to collect all the information you need to stay in touch with them down the line. 

Capture guests’ email addresses using automation tools so you have a way to reach out to them after they check out. This is especially important for guests who reserve via OTAs, as they probably won’t have to provide any contact information upon booking. 

One way to do so is via a digital guidebook. With Hostfully, you can create a custom Splash Page that your guests see as soon as they open your guidebook. To access the guidebook, they have to provide their email address, which you can then use for remarketing purposes.

Hostfully splash page screen.
Turn on the optional Splash Page feature to capture guest email addresses for remarketing.

You can also use a tool like StayFi, which is a vacation rental WiFi solution that requires guests to provide their email address to log onto your network. That way, you can collect the email addresses of everyone who stays at your property and not just the person who books or uses your guidebook. 

Pro tip: Hostfully integrates with StayFi, which makes it even easier to collect guests’ email addresses and send out marketing emails to your former guests. 

Hostfully integrating with stayfi

Create targeted campaigns 

Once you have your guests’ contact information, it’s time to reach out to them. Don’t be afraid to follow up with former guests: Creating targeted campaigns will keep your vacation home at the top of former guests’ minds. 

As we mentioned before, you can send out an email to former guests when you make updates to your property or to inform them about events happening in the area. You can also use automated messaging templates to schedule emails to guests offering a discount if they book again.

Having a customer relationship management (CRM) solution will be a big help come time to remarket to previous guests. By storing all your guests’ information in one convenient place, it will be easier to set up these automations and make remarketing a simple, scalable part of your operations.  

Pro tip: Hostfully integrates with Mailchimp, a leading email marketing platform that can help you run effective campaigns and bring in repeat business. 

Offer rebooking incentives

We’ve talked about offering discounts for repeat bookings, but feel free to get creative with your rebooking incentives. Everyone likes 15% off their next reservation, but think about what would really wow your guests. 

Offer a free tour of a local attraction or a discounted meal at a local restaurant. Talk to your local partners to set up a discount that attracts guests to their businesses and back to your property, and it’s a win-win for everyone. 

But just because you haven’t yet built those local partnerships doesn’t mean you can’t offer creative incentives. Offer a bottle of local wine if your guests previously came to the area to visit wineries, or a free mid-stay clean for reservations longer than a week.  

Just remember: Make booking directly on your website a requirement for these rebooking incentives, which will help you build a loyal guest base and minimize OTA commissions.

Provide frictionless check-in and check-out

Check-in and check-out can leave a lasting impression on your guests, and when these processes are smooth and easy, people are more likely to want to come back to your rental home. 

After all, the first impression a guest has of your property is when they check in. That’s why you want to keep this process as effortless as possible. 

New guests don’t want to be fussing over where to park or how to open the lock box with the keys, so make that information as clear and accessible as possible. 

Send out an automated message before arrival that gives your guests directions, parking information, and access instructions in one convenient place. And share your house manual and guide ahead of time so your guests know exactly where everything is located in the house as soon as they arrive. 

The same goes for check-out: Make sure your departure instructions are clearly displayed in your house manual, and offer your guests a late check-out when possible.

Share local expertise

Make guests want to come back to your vacation rental property by giving them an exceptional stay and sharing local expertise with them. If it’s a guest’s first time in the area, they’ll want to know where the locals eat, what the must-see attractions are, and what they simply can’t miss while they’re in town. 

And given our research shows that the majority of hosts share property information and local recommendations digitally, stay on top of industry trends by sharing your recommendations in a convenient digital guidebook that guests can access on their mobile device throughout their trip. 

That way, they know where to stop for a bite to eat while they’re in town and which museum they simply must save an afternoon for. Plus, having your expertise saves them hours they might spend scrolling through Google reviews or TripAdvisor to find the perfect family-friendly restaurant in the area. 

This is another opportunity to offer discounts with your local restaurant and tour guide partners: By advertising experiences in your guidebooks, guests can save when making their reservation through you. That brings you a commission and more business to your local partners. 

When your guests feel that you went out of your way to give them an exceptional stay, you’ll be at the front of their mind when they book their next trip to your area.

Hostfully Digital Guidebook showing local recommendations
Share your curated tips and recommendations and wow your guests using Hostfully Digital Guidebooks.
Source: Hostfully

Get more control over your booking calendar with repeat guests

Whether a guest booked with you on, Airbnb, or your direct booking site for their first stay, what matters most is where they go to reserve the second one. Drawing repeat guests to your website can help you create a steadier, more profitable source of revenue that will help you grow your vacation rental business. 

By following these strategies for bringing people back to your vacation rental, you can turn former visitors into returning guests and boost your bookings reliably without any commissions.

CTA for repeat guests