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Many vacation rental operators have seen a cool down in bookings and overall performance of their businesses this summer. This can be attributed to the vacation rental market normalization following the post-pandemic travel boom, ongoing economic instability and constantly changing guest expectations.

The reality is that the rental income has decreased and there is a need to balance this decline. During this webinar, the speakers discussed the potential for vacation rental professionals to optimize their revenue streams through strategic upselling. They explored the key strategies for successful vacation rental upsells in uncertain times.

Webinar Speakers:

François Gouelo, CEO & Co-Founder, Enso Connect

Jennifer Wilson, Business Development Manager, GuestView Guide

Madison Rifkin, CEO & Founder, Mount

Julia Rossi, Short-Term Rental Owner and Founder, Grey Domain

Moderator: Uvika Wahi, Head of Content and Community, Rental Scale-Up

Vacation Rental Upselling: Rental Scale-up Webinar Speakers

Watch the webinar recording

Why Upselling in Vacation Rentals?

Upselling in vacation rentals means offering additional services at additional cost, such as airport transfers, guided tours, or premium amenities. These services can elevate the stay experience for guests and increase revenue for operators.

Let’s look into the numbers for short-term rental upsells. Typically, 30% of a traveler’s budget is allocated to accommodations, while the remaining 70% is spent on experiences. Integrating these experiences into their upselling strategy enables hospitality providers to tap into this piece of the budget pie.

While being a valuable strategy at all times, upselling is especially vital when traditional revenue sources are at risk.

The Benefits of Upselling in Short-term Rentals

The speakers agreed that short-term rental upselling boosts revenue, elevates guest experience and offers a competitive edge to operators.

Increased Revenue

By offering additional services or amenities, you can increase the average transaction value of each booking.

Enhanced Guest Experience

Providing additional services or amenities can enhance the guest’s experience, leading to positive reviews and repeat bookings.

Competitive Advantage

Offering unique upsells can differentiate your property from competitors and make it more appealing to potential guests.

Examples of vacation rental upsells from industry experts

Our speakers shared their insights and examples of vacation rental upsell options. Here’s a breakdown of the valuable suggestions each speaker provided:

Jen highlighted the potential of basic yet essential services:

  • Offering late check-outs option for guests who wish to extend their stay a little longer.

  • Providing first-party services such as mid stay cleaning and equipment rental.

Julia emphasized the importance of collaborating with local vendors:

  • Partnering with local vendors, for example, a local picnic company offering custom picnics exclusive to the property.

  • Organizing events like bachelor parties and girls’ trips.

  • Having local vendors promote the property, which serves as a mutual benefit.

  • Using these partnerships as a great source of content for marketing purposes.

François shared ideas on enhancing the guest experience:

  • Prompting guests to purchase early check-in when they attempt to complete an online check-in ahead of their official check-in time.

  • Offering pool heating for guests who wish to enjoy the pool in cooler temperatures.

  • Offering fridge stocking and restocking for guests who appreciate grocery delivery services.

  • Using affiliate links (e.g., Uber) to provide transportation, luggage storage or other services while generating additional revenue.

Madi focused on unique local experiences:

  • Offering local vendor experiences, such as a mini pig experience.

  • Providing the opportunity for a hot air balloon experience.

  • Organizing a session with a mixologist at a local restaurant.

Vacation Rental Upselling Gap

Despite the clear benefits of upselling in hospitality, not many vacation rental operators are actually doing it. The survey of webinar attendees reveals that, despite their interest in upsells, 40% of operators have not yet implemented any upselling strategies. There is a significant gap in upselling strategies implementation. The majority of respondents are either not utilizing upselling at all, or are generating only a small portion of their revenue from it.

How much of your revenue coming from upsells

Vacation Rental Upselling Challenges

Although hotels have been practicing upselling for some time and are even escalating their efforts now, vacation rentals remain reluctant. This slower adoption of upselling strategies in short-term rentals, compared to hotels, has a reason. Short term rental properties are unique and often scattered across various locations, making operations more complex. Additionally, there is a widespread belief that true hospitality involves including everything in the initial cost. Some view upselling as an attempt to extract every last penny from guests.

We asked the vacation rental professionals about their biggest challenges with upsells. One third of the respondents are struggling to convince guests to opt for upsells. 30% need help to identify upsell opportunities. 19% wish they could streamline the upsell process and 19% don’t know how to start implementing upselling strategies.

This just confirms the pressing need for comprehensive education and guidance on effectively implementing upselling strategies in vacation rentals.

Biggest challenge in upselling

Identifying Opportunities for Upselling

To effectively implement upselling strategies, it is important to identify the opportunities that are most likely to resonate with your target audience. Our experts provided insightful suggestions on how to identify opportunities for upselling:

Julia recommended:

  • Taking into account your location and the experiences available in the vicinity. Tailor your offerings to the unique attractions and activities in your area.

  • Approaching sales and marketing as if you are building the property itself. This involves thinking strategically about the experiences and services that will enhance your property’s appeal.

  • Treating the content created for your brand as a product that consumers would want to purchase. This involves creating high-quality content that is valuable and appealing to your target audience.

François advised:

  • Consider whether the upsell will integrate seamlessly and at scale as part of your existing operations. This involves assessing the feasibility and scalability of each potential upsell.

  • Focusing more on basic services and less on experience-driven offerings. This involves identifying the essential services that all guests may need or desire during their stay.

  • Leverage historical booking data and information collected from your guests throughout the entire journey to identify trends and preferences.

Madi suggested:

  • Determining your guest avatar, which involves identifying the types of guests you are targeting and tailoring your offerings to their specific needs and preferences.

  • Identifying experiences that can be added without requiring significant additional time or effort on your part. This involves selecting offerings that are easy to implement and manage, while still providing value to your guests.

Using AI to supercharge your hospitality upselling strategy

Our conference speakers shared cutting-edge methods to develop a strong upselling strategy with the help of Generative AI. Incorporating large language models, like ChatGPT or GPT-4  into their guest experience platform or just using the chat, operators can:

Identify potential upsells based on your property data

Copying and pasting all your property information, including descriptions, locations and reviews into the Chat and asking it to suggest best upsells for the property.

Find the most sought-after local experiences in the area

Requesting the chat to create a list of the most searchable local attractions in a specific area. You will have to adjust and correct the prompt a couple of times until getting the desired list.

Craft upsell descriptions

Presenting the upsells in a manner that the guests will desire to experience the add-on. Quickly generating compelling copy to incorporate into your upselling tool.

How to successfully upsell to guests without being pushy or intrusive?

Once you have identified the opportunities for upselling, the next step is to implement these strategies effectively. Each speaker provided their insights:

Julia suggested:

  • Enhancing the guest experience by offering higher-quality items that guests will find appealing.

  • Being strategic about the placement of upsell offers.

  • Employing just-in-time messaging about local events, etc.

Madison, advised:

  • Leveraging experiences, as it is easier since guests often already inquire about them.

  • Including recommendations in the confirmation email as a gentle nudge.

  • Recognizing that guests often make last-minute decisions and may not purchase an experience or upsell until they are within their 72-hour window of consumption. Therefore, it is important to remind guests after they check in to review the upsells you have prepared.

François recommended:

  • Integrating upselling into the guest journey and avoiding overwhelming guests with notifications.

  • Providing tailored recommendations based on the type of guests (business, family, couples).

Additional suggestions that came up at the discussion:

Communicate Clearly

Ensure that the communication about the additional services or amenities is clear and concise. Use high-quality images and detailed descriptions to highlight the benefits of the upsell.

Offer Value

The additional services or amenities should provide genuine value to the guest. Avoid unnecessary upsells that do not enhance the guest’s experience or that may be perceived as opportunistic.

Leverage Technology

Use technology to facilitate the upselling process. For example, automated emails or messages can be sent to guests before their arrival, offering additional services or amenities that may enhance their stay. Having upsells available at one place on your guests’ phones, personalizing offerings and offering a one-click purchase experience can significantly increase your upsell conversion.

Monitoring and Adapting Your Strategy

It is important to continuously monitor the effectiveness of your upselling strategies and adapt them as necessary. Collect feedback from guests, analyze the uptake of additional services or amenities, and assess the impact on your overall revenue and guest satisfaction. By regularly reviewing and refining your approach, you can optimize your upselling strategy for success in these uncertain times.

How often do you revise your upselling offering to guests

The results of the conference poll revealed that the majority of respondents, 58%, are reviewing their upselling offerings to guests once or twice a year. Meanwhile, 32% of respondents admitted to never reviewing their offerings to guests, and a mere 11% are assessing their upsells on a monthly basis.

Lack of control over your upselling offerings may lead to missed opportunities and suboptimal results. Regular monitoring and adjustment of upselling strategies are essential to maximize their effectiveness and ensure they continue to meet the needs of guests.

How can vacation rental professionals offer upsells to guests ?

Offering upsells to guests can be done in various ways, each with its own advantages. Here are some methods property managers can use to offer upsells to their guests:

Email or Messaging

 Sending personalized emails or messages to guests before their arrival is an effective way to offer additional services or amenities. This can include information on airport transfers, equipment rentals, or unique local experiences. Be sure to include compelling descriptions and images to make the offerings as attractive as possible.

Guest App

A mobile app designed for your guests can be a convenient way for them to access and purchase upsell offerings during their stay. The app can include information on available services and amenities, as well as local experiences and attractions.

In-House Screen

Screens in the property, such as a smart TV or a tablet, can be used to display upsell offerings to guests during their stay. This can include information on available services and amenities, as well as recommendations for local experiences and attractions.

QR Codes

 Placing QR codes strategically around the property or in the welcome booklet can direct guests to a web page or app where they can view and purchase upsell offerings. This is a convenient way for guests to access the information at their own leisure.


Traditional face-to-face interaction can also be an effective way to offer upsells to guests. This can be done at check-in or during the guest’s stay by trained staff who can explain the benefits of the additional services or amenities.

Property Website

The property’s website is an ideal platform to showcase upsell offerings. Guests often visit the property’s website before their stay, making it a prime opportunity to present additional services, amenities, or experiences that may enhance their stay.

Remember, the key to successful upselling is to offer genuine value to your guests and to present the offerings in a way that enhances their experience. By utilizing a combination of these methods, hosts and managers can effectively offer upsells to their guests and maximize their revenue potential.

Preffered method of presenting upsells to guests


While the current climate presents numerous challenges for the vacation rental industry, strategic upselling presents an opportunity to optimize revenue streams and enhance the guest experience. By understanding your guests’ needs, offering genuine value, and leveraging technology, you can implement successful upselling strategies that will benefit both your business and your guests.

Learn how Enso Connect can increase your revenue with upsells

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