How to encourage repeat bookings from past guests?

For vacation rental owners, having a strong repeat booking strategy isn’t just a nice-to-have—it’s essential. It stabilizes your income, makes your revenue more predictable, and reduces your reliance on constantly acquiring brand-new guests through costly platforms like Airbnb or Vrbo.

So how do you actually get past guests to come back—and bring their friends with them?

Start by Capturing Every Guest’s Email

One of the best ways to build a foundation for repeat bookings is to capture the emails of all guests who stay at your property—not just the person who made the reservation.

There are simple tools for this. Many vacation rental owners now use Wi-Fi login systems similar to what you’d find at a Starbucks or Peet’s Coffee. To access the Wi-Fi, each guest inputs their email address, which feeds directly into your database. It’s a low-friction, high-impact way to grow your audience of potential repeat visitors.

Nurture the Relationship—Don’t Spam It

Once you have those emails, don’t just blast generic promotions. A quarterly newsletter works best when it genuinely adds value.

Highlight upcoming local events, seasonal activities, or new experiences your guests might enjoy on their next stay. Sprinkle in insider tips and recommendations they won’t find on TripAdvisor. Then, at the end, include a soft call to action—like a link to check availability, or a subtle offer for a returning guest discount.

Done well, this doesn’t feel like marketing—it feels like an invitation.

Turn Guests Into Evangelists

The real magic happens when your past guests don’t just come back themselves but tell others about you.

Great stays get shared on social media. When your guest’s friends ask, “Where was that gorgeous place in Wine Country you stayed?”—you want to make it easy for them to forward your name, your direct booking link, or your newsletter. This turns each guest into a mini-marketer for your property.

Add a Few Gentle Nudges

Email isn’t the only tool. You can run retargeting ads to remind past guests of their stay or offer a limited-time promo code for their next visit. Some owners also use text-based campaigns for special offers or priority booking windows during peak seasons.

These small nudges are often enough to tip someone from thinking about rebooking to actually doing it.

No Repeat Bookings Without a Great First Stay

Of course, none of this works if your guest’s first stay didn’t deliver. No fancy email or ad will convince someone to return if the property fell short.

That’s why high operational standards are so critical. It’s exactly why we do what we do at Vinifera Homes. A sophisticated property manager who sweats the details is the backbone of any repeat booking strategy—because the guest’s experience has to be worth repeating.

Why Direct Repeat Bookings Matter

One final reason repeat bookings matter: they help you cut out platform fees.

When a guest books again through Airbnb or Vrbo, they pay a service fee—sometimes up to 15%—which can be the difference between booking or not. With a direct booking, you can pass some of that savings back to the guest as a discount while still netting more revenue than you would through a third-party site. It’s a win-win.

What We Aim For at Vinifera Homes

At Vinifera Homes, we set a high bar. After the first year of managing a property, our goal is for at least 30% of bookings to come from repeat guests. If we’re not hitting that, we treat it as a miss—and we get to work refining our strategy until we do.

The result? More predictable revenue, loyal guests who feel like insiders, and fewer booking fees going to big platforms instead of your bottom line.

Written by Anish Patel, Head of Owner Relations at Vinifera Homes (anish@viniferahomes.com)