Beyond the Stay: Mastering Upsells & Guest Experience in Short-Term Rentals

In this episode of the Hospitable Hosts podcast, we had a panel discussion on incorporating upsells into the short-term rental business and ways to enhance the guest experience. We were joined by Mike O'Connell, Founder of Happy Guest. This innovative platform helps hosts delight guests with automated check-ins, smart upsells, and user-friendly digital guidebooks packed with must-know info and local tips.   

We were also joined by 4 Hospitable hosts who contributed their unique perspectives to the conversation. Meet Marisa Grover, a podcaster and property manager of 40+ properties in Texas; Virginia Aucoin, the owner of Bonnabel Haus Properties offering property management services across Louisiana and Idaho; Nessa Fuentes, the operations manager at Navastay Vacations, who manages about 31 properties in the Treasure Coast, Florida,  and Coleman Davis, who owns and operates several STR properties called Ghost Town Casitas in Texas.

Mike helped Miles to facilitate a productive discussion, and Marisa, Virginia, Nessa, and Coleman shared their experiences of implementing upsells and how Happy Guest and Hospitable help them simplify their workload, offer upsells with minimal effort, and elevate the guest experience. Our guests also discussed effective strategies that help them win more great reviews and encourage travelers to book directly.

Press Play now to hear different viewpoints on vacation rental upsells and discover how offering additional services that align with guest preferences helps improve guest experience, earn 5-star reviews, and get repeat bookings.

If you prefer to read the highlights, we've got a summary of the key takeaways below.

Why Did They Start Doing Upsells?

Coleman explains that upselling firewood is not about gaining more revenue—it's about offering extras to elevate the guest experience, and he needs tools to do it efficiently. "Because we're small, it'd be a big expense and a huge amount of time to get it going. However, with Happy Guest, it was just really easy. It was hard not to say yes to it because the process is so seamless."

Marisa says that when she first started hosting, she wanted to create opportunities for people to buy products. So she purchased $200 worth of things in a dollar store and stocked her pantry, keeping everything organized in containers with labels so that her guests could scan the QR codes that took them to PayPal.

Soon, she discovered that her guests didn't want to buy her products, and the process was "so cumbersome" because her cleaners had to keep track of the inventory and take pictures every time. "So I just stopped doing upsells for a while for a couple of years in my business until I was able to connect with Happy Guest and Hospitable and just make this such a streamlined process because for so long, it was a headache, and it was not serving me or the guests at all."

Nessa admits that upselling was first about generating extra revenue. “But over time, we realized offering something special for our guests was really fun. It sets us apart from other property managers and gives a little personal touch to their stay."

Virginia explained that she manages properties in a high-end market, so she needs to differentiate herself. She noticed that offering upsells is a value add that makes her listings more attractive even if people don't purchase these add-ons. "I can also let my owners know that it exists. It's a way to keep our guests returning because of some of our upsells."

Popular Upsells

When discussing the most popular upsells in their portfolio, Virginia points out that her guests were demanding early check-in. Offering it to them now as an upsell saves her "so much time in awkward conversations with guests."

Nessa adds that she has switched to an automated early check-in process with the help of Happy Guest, so everything is much easier now because it requires zero host interaction. Since most of her guests are traveling to celebrate something, she offers different birthday and wedding anniversary packages to add "that little extra touch."  

Marisa underlines that upselling is not limited to standard early check-ins and late check-outs—you need to be creative and think outside the box. "There are so many ways you can create hospitality in upselling without feeling like you're trying to nickel and dime people throughout their entire stay."

The Optimal Timing to Offer an Upsell

Virginia uses a digital guidebook to introduce upsells to her guests as an opportunity without seeming pushy. "As soon as they can access the guidebook, it's there. It's a little tab, so it's not in your face. I'm not texting them saying, "Buy something." But if they want to explore, they can."

Nessa does it after booking confirmation and tailors specific options to specific guests. "We use Hospitable to send an automated message asking, "Hey, are you guys celebrating anything? "If they answer that question, we'll say, "Hey, we have all these upsells for your celebrations if you want something upon your arrival or during your stay."

Coleman says he includes a link to his store in his check-in instructions, communicates about upsell opportunities in messages, explains the process, and tries to make it "casual."  

Marisa likes that with automated upsells, she can allow guests to shop, so they spend the money and are grateful for the opportunity. "We're not forcing them. We're not asking them for money. Like it's just there, and if you want to browse through what we offer and look at the different options, now it becomes a service."

Fulfilling Automated Upsells

Nessa shares her operational process for fulfilling upsells: "We have an automated message that goes out and asks if they're celebrating anything. From there, they are directed to Happy Guest, where they can see what we have. Once that's done, Happy Guests will handle the payments. They send me a notification. I get the notification. I approve the notification. All I have to do is fulfill it and take it there."

Marisa emphasizes that since upselling is a completely automated process, it feels like "making money while you sleep" because she doesn't have to do anything. "It's just like income and creating guest experiences without the backend work." Coleman points out that the automated upselling process is seamless, and he has never had negative experiences with it.

Getting Positive Reviews

"As soon as I started working with Happy Guest, people go out of the way to mention the service that I provide, which, to be honest, I'm not doing anything too different," Virginia says. "I've always been super responsive, but guests love that everything is just right there, all in one place."

Marisa and Nessa point out that they always get great reviews when they allow guests to check in early or check out later because people are grateful for the hospitality.

Tune in to the full episode of the Hospitable Hosts Podcast to listen to an informative discussion of how upselling transforms the guest experience in short-term rentals and discover the diversity of opinions and experiences.