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Short-term rental upselling: The untapped potential of your properties

Upselling to guests can both enhance a guest’s vacation, and elevate your profits. It’s something that more and more property managers and owners are starting to do. And, if you think about it— Hotels have been doing this for decades, and for good reason.

First and foremost, offering upsells allows you to stand out from the crowd and offer products or services to enhance your guests’ experience that no one else is offering. Which means, your guests are more likely to book through you again, and recommend your company to friends and family. Of course, offering upsells brings an additional revenue on top of nightly rates. Guests’ travel budget is not limited to rent, and property managers should tap into this opportunity to increase revenue and profit margins.

In this article we’ll get into the art of upselling in short-term rentals, including:

By the end, you’ll be familiar with how you can take your rental business to new heights by capitalizing on upselling opportunities.

Woman arriving at vacation accommodation and looking out the window

Are upselling and cross-selling the same thing?

Well, not exactly. The terms “upselling” and “cross-selling” are often used interchangeably, but they are slightly different 

Upselling refers to the practice of encouraging guests to upgrade their booking to a higher-priced accommodation option or to add additional services or amenities to their existing reservation. The goal of upselling is to persuade guests to spend more money by offering them enhanced options. For example, an accommodation provider might offer guests the opportunity to upgrade from a standard unit to a premium one with more space and luxurious amenities — for an additional fee. Upselling is about promoting an upgrade within the same category or product line.

Cross-selling, on the other hand, involves offering guests additional products or services that complement their original booking but may fall outside the scope of the accommodation itself. It aims to expand the guest’s purchase by suggesting related or supplementary offerings. For instance, an accommodation provider might cross-sell services such as spa treatments, airport transfers, local tours, or restaurant reservations to enhance the guest’s experience. The focus is on offering additional options beyond the core accommodation product.

Offering upsells without being too pushy 

There is a fine line between offering extras that will elevate your guest’s vacation, and coming across as pushy or salesy. The key here is to approach upsells with a genuine desire to enhance the guest’s stay.

Our first recommendation is to tailor the upsell options according to the specific guests. This way you can provide helpful enhancements to your guest’s stay without bombarding them with a long list of upsells. Our next recommendation relates to timing. Time it right. Wait for the appropriate moment to offer your upsell and don’t offer everything at once – but more on this later…

And finally, communication. The way you communicate about an upsell opportunity is key. When presenting upsell options be sure you are highlighting the added value to the guest. 

Couple signing a contract

The optimal timing for offering upsells 

The right offer, at the right time can really make a difference! The best time will vary depending on the specific nature of the upsell, and the length of your guest’s stay. Here’s a few examples:

Pre-booking

Including certain upsell options during the initial booking process will set you apart. At this point, you would look to offer additional services or amenities such as early check-in or late check-out, a premium package that includes a welcome basket, a grocery delivery service, airport transfer, or access to exclusive amenities.

You may not see many guests buy these add-ons when they book, as the booking itself is a big expense. But knowing these options are there will make your listings more attractive. 

Pre-arrival

According to Enso Connect, a guest experience operating system, a week or two before arrival is a good time to offer those upsells that weren’t purchased at the booking phase. Now that your guests are closer to arriving they may actually decide they want to be picked up at the airport, and would like some groceries to be ready for when they arrive. They may even have just checked their travel times and realized that an early check-in would be nice. 

Upon arrival 

This can be an ideal time to present upsell options, as guests are excited about their stay and open to exploring additional offerings.

During the stay

Pay attention to your guests’ needs and preferences throughout their stay. If you notice they might benefit from or enjoy certain upsell options, such as a late checkout, a private chef, or a local experience, you can offer these suggestions in a friendly and non-intrusive manner. Timing is crucial here, as you don’t want to interrupt their experience or make them feel pressured.

Remember, it’s important to strike a balance between offering upsells and respecting your guests’ privacy and comfort. Always prioritize their experience and ensure that any upsell suggestions are relevant, valuable, and aligned with their interests.

Man looking at clock in waiting room

Which upsells should I offer?

We spoke to some of our upsell partners to discover the most popular upsells in their portfolios.

First place: Late checkout

Second place: Early check-in 

Third place: Pet fees

There are plenty more upsell options that are also very popular amongst guests including mid-stay cleaning, e-bikes/e-scooters, and stocked fridge.

Upsell partners – our top picks 

There are many many options and ways to put your offers in front of guests. Here are some of our favorite upsell partners – that make upselling seamless. 

1. Duve 

Duve is an end-to-end guest management system for upsell services (and so much more), with a big emphasis on personalization. Duve has many upsell templates and will connect you with the 3rd party suppliers to deliver on these – and is of course completely customizable based on the guests you are hosting. Duve upsell options include breakfast in bed, spa packages, bike tours, show tickets, and more. Duve also allows you to offer guests different transportation options and check-in methods — which can all be purchased in a few clicks. 

With Duve’s built-in guest app, guests can communicate with your staff in their native language (automatically translated), purchase upsells with the click-of-a-button, and access information about hotel facilities and recommendations. Guests can also open room doors without the need for a physical keycard – all while navigating through a web-app that’s fully branded according to your company.

2. YourWelcome

YourWelcome provides guests with the option to purchase upsells during their stay on an easy-to-operate tablet. 

It is super simple. Property managers connect their payment provider (e.g. Stripe) to YourWelcome and set up any service they wish to sell. Guests are also able to request a service by entering their credit card details, and property owners can accept or decline any request.

The advantage of a tablet is that you are able to offer guests upsells without being pushy by sending intrusive texts and emails. According to YourWelcome the vast majority of owners market late checkouts to guests under an ‘upgrade your stay’ banner on the tablets – and this is highly effective.

In addition, YoueWelcome has an internal dashboard that allows property managers to experiment with pricing, images, and more. The dashboard provides insight into the number of clicks different upsell options get as well as trends around drop-offs in the buying journey, which really allows property managers to refine their upsell strategy. 

YourWelcome is available in a number of languages including English (UK & American), French, German, Spanish, Italian, Portuguese, Japanese, and Mandarin. 

3. DACK

DACK’s smart guest platform offers four categories of upsells; digitally enabled, goods and services, local vendors, and pre-built 3rd party connections. Many of the services DACK provides are automated meaning no extra work for property managers. 

DACK sends emails, text messages, and push notifications based on smart logic, such as the first time a guest opens the door, or a push alert when a unit is vacant. Message routing can send guests to virtually any page in the app directly from a push notification – a powerful way to get their eyes on specific content. 

The DACK Platform acts as a digital concierge and personal tour guide. The customizable local recommendation section and an engaging map view, enable guests to have a seamless experience viewing curated recommendations. Property managers can add text, pictures, videos as well as favorite dishes to recommendations. The platform even allows links out to various booking and reservation platforms.   

DACK operates in the US, Mexico, Canada, the UK, and Australia, and the web application is translatable into virtually any language.

4. Enso Connect 

Enso Connect provides a dynamic guest-facing web app, known as the “boarding pass” that guides guests through the entire stay, from booking to checkout and beyond. Upsells can be offered and prompted at any stage of the journey.

After the booking, property managers provide the guest with the Boarding Pass link. It serves as a compendium of the stay, encompassing verification steps, agreements, applicable fees, available upsells, step-by-step check-in instructions, lock codes, property and neighborhood guidebooks, and more. 

With Enso Connect upsell capabilities, operators can facilitate Airbnb early check-in/checkout fees, pet fees and more. Property managers can create custom upsells, integrating multiple Stripe accounts for direct sales. 

Additionally, the platform allows operators to incorporate affiliate links and local partner links, expanding the services available to guests and diversifying revenue streams. This includes offering services like Uber, Turo, OpenTable, Viator, and establishing affiliate contracts with local service providers such as yoga teachers, travel guides, private chefs, massage therapists, and more.

Enso Connect’s capability to create customized upsells allows it to cater to various types of hospitality businesses ranging from Airbnb superhosts managing a few listings to enterprise property management companies overseeing thousands of properties. The upsells can be tailored to accommodate each distinct segment of the lodging market, including vacation homes, aparthotels, and more.

Enso Connect operates globally and supports over 150 languages. With the introduction of the newly announced Enso AI, Enso-connected operators will be able to effortlessly create custom upsells in a matter of seconds in any language available in GPT-4, powering this feature.  

5. Mount

Mount is an online marketplace that allows hosts to offer curated local experiences and stay enhancement add-ons, such as e-bikes and paddleboards, to their guests with ease and convenience.

With Mount, property managers are able to promote their upsells and experiences primarily pre-arrival and during the stay. Mount guests are given access to the experiences available to them after they have booked their accommodation. On the Mount host page, guests can easily review and select both on-site and local experiences. After the traveler has paid for their experience(s), they will receive email confirmation with the necessary information to enjoy their experience. For example, if they have selected to rent e-bikes, they will be given the location of the e-bikes, the necessary instructions to unlock them, and any other useful information the host or vendors need them to know to stay safe and have a great time.

Mount is primarily available in the United States and typically caters to local hosts and property managers overseeing 20 properties or less. 

6. GuestView Guide 

GuestView Guide is an interactive, wall-mounted digital concierge, that provides a number of products and services in the realms of guest communication, personalized experiences, and upsells. It allows property managers to offer and promote just about any service, with payment going through the guest’s mobile device. 

GuestView Guide displays upsell offers through a slideshow feature that is tailorable to every guest. The high visibility, strategic placement, and the interactive display of GuestView Guide allows property managers to offer more upsells in a dynamic way, versus the out-of-sight out-of-mind apps, outdated paper guidebooks, and forgotten emails. 

GuestView Guide currently serves vacation rentals in the United States, Puerto Rico, and the U.S. Virgin Islands. The display is in English.  

Final thoughts

Incorporating upsells into your short-term rental business doesn’t have to be an overwhelming task. By leveraging the support of various partners and utilizing user-friendly tools, you can seamlessly offer additional services and amenities to your guests. The minimal efforts required to implement upsells are undoubtedly worth the benefits they bring. So take advantage of this opportunity to enhance your guests’ experience, boost your revenue, and elevate your short-term rental business to new heights. 

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