Short-Term Rental Upsells: Elevating Guest Experiences and Unlocking New Revenue Streams

Gone are the days when nightly rates were the sole source of income for short-term rental hosts.

In the dance that is balancing guest experience and optimizing profit, upselling is a strategy that lets vacation rental property managers enhance guest stays and uncover hidden revenue.

Read on to learn more about what upselling is, how to be strategic and targeted in what you’re upselling and how to use Hostaway to upsell your guests and bring home higher profits.

What is Upselling? The Art of Offering More

Upselling is a sales technique encouraging customers to choose a more expensive product, upgrades or add-ons. Considering that accommodation accounts for only about 30% of a guest’s vacation budget, there is plenty of opportunity for Airbnb hosts and property managers to tap into this additional revenue.

What does upselling look like in practice? It's about offering those additional services, rentals and experiences that guests might not even know they wanted and are willing to pay for to give themselves a memorable vacation.

Did you know?: Hostaway users have earned an average of $4,400 in additional revenue through upselling in 2023?

Guests are more than willing to invest in enhancing their travel experiences — it’s up to vacation rental hosts to cash in. What’s more, upselling can lead to higher ratings, better reviews and repeat business.

When Should You Upsell? Timing is Everything

Conventional wisdom would suggest upselling during the booking phase is the way to go. Dive deeper into the psychology of purchasing, however, and a different story is revealed.

Guests generally go into booking accommodation with financial parameters in mind — a.k.a a budget. As such, they are less likely to overspend at the booking stage.

Post-booking, as the dust settles and anticipation grows, guests are more receptive to enhancing their upcoming experience. It's in this pre-arrival euphoria, a week or two before check-in, that upselling finds its most fertile ground.

This strategic timing aligns with the natural ebb and flow of consumer psychology, maximizing the likelihood of guests opting for those little extras that make their stay special.

Beyond the Booking: A Strategy for Upselling Success

Here’s the play: understand your guests’ preferences and the unique potential of the vacation rental property you operate. Then leverage Hostaway for effortless upselling.

Here's an upselling strategy that boosts your revenue and elevates your guests’ journey.

1. Figure out your upselling opportunities

The foundation of a successful upselling strategy lies in deeply understanding your guests and the context of their stays. Analyze past booking data and feedback to identify trends and preferences that can guide your upselling efforts.

For instance, if your property is a favorite among couples, consider offering a romance package complete with a bottle of champagne, chocolates and a late checkout option. Similarly, if families frequent your property, a picnic package or a family adventure tour might be more appealing.

Seasonality and market trends also play a critical role. While a sauna might be an attractive upsell during the colder months, it's less likely to appeal during a hot summer. According to Hostaway VP of Product Maria Lopez, popular upsells include pet fees, extra guest fees, early check-ins and late check-outs and mid-stay cleaning. In the pre-ordered category top-sellers include romance packages, a vigneron picnic hamper, golf cart, crib and high chair. Meanwhile ski rentals and excursions are popular local experience upsells.

2. Automate upselling with Hostaway

Leverage Hostaway’s short-term rental software to automate the upselling process across all your listings, on booking platforms or direct bookings. Trigger your messaging to reach guests during the pre-arrival phase when the are most open to additional purchases.

Beyond pre-arrival upsells, stay extensions and late checkouts are high-converting upsells that you can leverage during a guest’s stay. Third-party tools like HostAI (available in the Hostaway marketplace) can also help automate the detection of these in-stay upsells so that you can turn calendar openings into revenue.

3. Enhance the Guest Portal experience

Your Hostaway Guest Portal is prime real estate for showcasing your upsells. Enhance this space with compelling video content, high-quality images and attractive descriptions and transform the upselling process into an integral part of the guest's journey.

4. Upsell on your direct booking website

Don't overlook the power of your direct booking website as an upselling platform. Create an entire page or more to showcase your upsells in their best light. Entice guests with high-quality content.

Incorporate the Hostaway booking engine to make the booking process seamless.

5. Customize upsells for each property

Tailor your upsell offers to reflect the unique character and amenities of each vacation rental property and the preferences of the guests they attract.

This means not only choosing the right types of upsells but also customizing the presentation and messaging for each short-term rental property. A one-size-fits-all approach is less effective than upsells that feel specifically curated for each listing.

6. Communicate costs clearly

Transparency is crucial when it comes to upselling.

Clearly communicate the costs associated with each upsell option, ensuring there are no surprises at checkout. This transparency builds trust and can lead to higher guest satisfaction, as guests appreciate knowing exactly what they're getting and at what cost.

7. Upsell extra amenities

Capitalize on amenities that are already in place.

Does your cabin have a hot tub? Upsell it to guests rather than providing it for free. Does your resort property have a pool? Provide pool heating for an additional fee.

This strategy not only generates extra revenue but also adds a layer of exclusivity and luxury to the guest's stay.

8. Use upselling to impose house rules

Upselling can also serve as a clever strategy to enforce house rules without compromising guest experience.

Let's say you’re worried about guests raising the thermostat. Instead of setting strict rules that limit how much guests can increase the heat, offer the option to increase the temperature higher for an additional fee.

This approach not only ensures guests enjoy their stay in their preferred conditions but does not require you to take on the additional task of being a hall monitor.

Ready, Steady, Go Upsell!

In today's fiercely competitive short term vacation rental landscape, the stakes have never been higher. For owners and property managers alike, the challenges are mounting: costs are increasing, guest expectations are reaching new heights and the battle for glowing reviews has become more intense than ever.

In this environment, discovering new revenue streams isn't just advantageous — it's essential — and upselling delivers.

Book a free demo with Hostaway and see how we can get more money in your pocket with upsells.