A Property Manager's Guide to Upselling Experiences

Most short-term rental operators build their guest experience around the day someone arrives: an in-person check-in, a printed guidebook, a welcome message with local restaurant recommendations. It’s a natural place to put the effort in, once you have the guest’s full attention. However, according to Localbird’s experience booking data, most of that effort lands after the guest has already decided what they’re doing and where they’re spending during the stay.

Across more than 7,500 experience bookings in the last 12 months, 74% were booked before check-in. Guides, welcome baskets and in-app prompts delivered on arrival day are competing for attention once most of the trip’s biggest spending decisions have already been made.

What gets planned in advance

While the majority of experiences are booked before arrival, not every experience follows the same timeline. Higher-value bookings or those with limited availability such as private chefs, boat charters and guided tours tend to get locked in well ahead of arrival. Lower-cost or more spontaneous choices, like a taxi to dinner or a last-minute massage, usually get arranged once the guest is already on the ground and knows their schedule.

That split has a direct consequence for anyone planning promotion around the guest journey. Experiences with longer booking windows need to be visible while guests are still planning their trip and woven into pre-arrival communication. More spontaneous services can be surfaced closer to check-in or during the stay, when the need for them actually arises.

The short-term rental manager who waits until arrival to surface a private chef or a sunset cruise is competing with whatever the guest already found and booked weeks earlier, on their own or through another provider.

The spending gap between guest types is wider than it looks

At properties charging $500 or more per night, 44% of guests engage with a digital concierge, and 18% go on to book an experience. At properties under $100 per night, those numbers drop to 35% and 4%. Average spend per stay follows a similar pattern: guests at premium properties spend around $1,000 on experiences, compared with $166 at budget properties.

It’s logical, sure: guests with more to spend are also more likely to choose pricier experiences. What’s more interesting for property managers is that guests at premium properties are more likely to book a second or third time during a single stay: a private chef the first night, a boat trip mid-week, a massage before departure. For property managers, that creates an opportunity that extends well beyond the first booking. Staying visible throughout the guest journey gives them a better chance of capturing a greater share of that spend.

A single welcome message might encourage the guest to book once, but it is unlikely to drive those second or third bookings as the stay unfolds.

What property managers can do differently

A few adjustments can shift where the promotional effort goes, without adding much operational load.

• Start communication early. Rather than waiting for check-in or just before, send experience recommendations as soon as a booking is confirmed, while guests are still planning their itinerary. This is the window where the highest-value, longest-lead-time experiences are often decided.
• Sequence experiences by how far ahead they’re typically booked. Lead with tours, private chefs, and other higher-ticket experiences in early pre-arrival messages. Save convenience items like local transport and massages for closer to arrival or during the stay, when guests are more likely to want them on short notice.
• Give more guidance to higher-end guests. A guest paying more per night is statistically more likely to book, spend more, and book again. That makes personalization particularly valuable: tailor what they see ahead of arrival based on the property, destination and type of stay, then continue surfacing relevant options once they arrive.
• Build in a second and third prompt during the stay. A guest who has already booked one experience has already demonstrated an appetite for more. A short mid-stay message asking how their previous experience went opens the window to further bookings.

The in-stay guidebook still has a role. Convenience bookings will keep happening close to the moment of need, and weather or mood can always change plans. But when you’re dealing with hundreds or thousands of bookings, the bigger commercial opportunity comes from building the guest journey around when people actually plan and spend.

Redesigning around that timeline doesn’t require a major operational shift: a few automated messages, sent earlier and sequenced by guest type and booking behaviour, cover most of it. What needs to change is the way property managers think about experiences and services, making them part of the early guest journey rather than add-ons.