Wonder’s Top-Performing Upsells
Bruno’s philosophy: keep the menu focused. After experimenting with a broader catalog, Wonder refined their offerings to the items guests actually want and those that enhance the experience without adding too much operational chaos.
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Upsell
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Why It Works
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Benefits
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Pool Heating
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Orlando winters mean guests want warm pools, but heating must be scheduled in advance. Wonder charges $25-40/day. A price that covers electricity costs and ensures a smooth, no-surprise experience for guests. Peak demand: October through April.
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Guests enjoy a warm pool from day one without the hassle of a last-minute request. Homeowners receive the revenue directly, boosting their annual income from the property.
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BBQ Grill Delivery
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Three and four-burner grills with utensils, delivered to the property. Perfect for families who want to cook out without lugging equipment. Wonder maintains and cleans the grills, protecting the property while enhancing the stay.
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Guests get a hotel-style amenity without packing or planning. Properties benefit from professional grill maintenance rather than guest-damaged equipment left behind.
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Baby & Family Essentials
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Cribs, high chairs, and other baby items for families traveling light, particularly popular with Disney-bound guests who can’t check a pack-n-play. Removes a major travel friction point.
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Guests arrive lighter and less stressed, especially families flying in. Eliminating the need to rent or ship gear makes Wonder the easy choice for repeat family bookings.
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Early Check-in/Late Checkout
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Flexible check-in/out timing for guests who need more control over their travel day. Revenue benefit is straightforward; operational coordination is handled inside Breezeway tasks.
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Guests get flexibility that feels premium. Operations benefit from structured scheduling rather than ad hoc requests, keeping the team running efficiently across properties.
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The Wonder Approach: Proactive, Persistent, Personal
Bruno attributes Wonder’s upsell success not to complicated strategy, but to consistent execution rooted in hospitality fundamentals. His team communicates upsell offers at every meaningful touchpoint throughout the guest journey — before arrival, close to check-in, and through the Breezeway Guide.
A Multi-Touch Communication Strategy
Wonder surfaces upsell opportunities at four pivotal points of the guest journey:
- 2–3 days after booking: an introductory message about available extras
- 30 days before arrival: a reminder with full service details
- 2 weeks before arrival: another prompt as the stay approaches
- 3 days before check-in: a final offer window before operations locks in scheduling
Each message clearly explains not just what’s available, but why booking in advance matters, setting expectations and reducing friction at check-in.
Upsells Beyond the Transaction
When a guest purchases an upsell, the work doesn't stop at checkout. Breezeway automatically generates a scheduled task for the field team. No manual handoff, no chasing confirmations. For a company running 60+ employees across nearly 500 properties, that kind of behind-the-scenes coordination is what separates a smooth operation from a reactive one. Upsells aren't just a revenue line; they're a scheduling signal that keeps Wonder's team operating efficiently across every property, every stay.
That same inventory of services also gives Bruno's team something equally valuable: options. When a guest has a frustrating experience, a complimentary BBQ delivery or a poolside upgrade can turn the moment around fast. The cost is minimal. The goodwill is significant.
The Impact
Revenue: 4.3% Upsell Contribution
Upsells now represent approximately 4.3% of Wonder’s total business revenue monthly, a meaningful contribution that flows directly into additional income streams for both the company and its homeowners.
Direct Value to Homeowners
The majority of upsell revenue — particularly pool heating — flows directly to property owners as additional income. Bruno views this as one of the most compelling owner-facing benefits: it improves ADR, increases year-end earnings, and demonstrates that Wonder is working hard to maximize every stay.
“The pool heater revenue goes straight to the homeowners. At the end of the year, they see the total and say 'Wonder Vacation Homes is doing good." It gives them another income and I'm happy to help them."
Better Guest Experience, Fewer Surprises
By communicating expectations clearly and in writing across multiple touchpoints, Wonder dramatically reduces check-in friction. Guests who have already arranged pool heating or a BBQ delivery arrive knowing exactly what to expect.
Bruno’s Advice to Other Property Managers
For operators hesitant to launch an upsell program due to operational concerns, Bruno has a direct message:
His top tips:
- Start simple. Pool heating and BBQ delivery drove the most volume. Don’t over-engineer the menu.
- Communicate early and often, but not excessively. Four touchpoints before arrival is the sweet spot.
- Put upsells in the Guide so they’re always accessible, not just in messages. This also allows guests to take advantage outside of the designated touchpoints.
- Use upsells as a service recovery tool. A complimentary extra can turn a frustrated guest into a loyal one.
- Think about the owner, not just the guest. Upsell revenue is one of the easiest ways to show owners you’re maximizing their property’s performance.
