Demystifying Upsells: Breaking Down the Top 5 Myths About Add-Ons in Vacation Rentals
A recent KeyData survey reveals an interesting trend for 2025: while 74% of property managers plan to add more properties and 77% are focusing on pricing optimization, only 33% are considering upsells.
Let’s pause on that. Adding properties means multiplying your workload - more maintenance, more guest communications, more owner relationships, and more of everything. But what if you could boost revenue by 30% from your existing properties without all that extra work?
This is what we call “squeezing the last drop of revenue from your listings.” Upsells can generate significant income from rentals you already manage, without the complexity of onboarding new properties or managing more owner relationships.
In our previous newsletter, we explored the untapped potential of upsells and the substantial revenue boost they can bring to your bottom line. Today, we’ll tackle the elephant in the room:
👉 Why are only 33% of managers planning to leverage upsells in 2025, while most focus on the more labor-intensive path of adding inventory?
Property managers often hesitate with upsells, but those who try it consistently wish they’d started sooner. Let’s debunk the top 5 myths holding short-term rental businesses back from this revenue opportunity.
Myth 1. Logistics, or “The No Time Myth”
🙅 "I don't have time to provide early check-ins or late check-outs; what happens if I have guests before or after the request?"
Reality Check
Automation Makes it Simple
Modern automation tools handle the entire process - from offering and confirming to scheduling cleaning crews. Yes, you can't automate the cleaning, but you can make it faster and more seamless.
Flexibility is Key
Think flexible, not extreme. A 1 PM early check-in or noon checkout can be just as appealing to guests as more extended windows. You maintain control of your schedule while monetizing those extra hours that naturally exist between bookings.
Implementation Tips
✔️ Accept Requests on Your Timeline. There’s no rush; wait until you have visibility of your schedule.
✔️ Secure with a Credit Card. Take a card imprint and charge automatically upon confirmation.
✔️ Automate Communication. Set up notifications in your messaging system to confirm availability.
Myth 2. Guest Communication, or “The Less Touchpoints Myth”
🙅🏼 "No add-ons here. I'm certainly not looking for any more reasons to deal with the guests."
Reality Check
Strategic upsells reduce guest messages by anticipating needs and automating common requests. Plus, guests appreciate having options at their fingertips.
Proactive vs. Reactive
By setting up your upsell offerings in advance, you transform back-and-forth conversations into one-click approvals. This means your system does the selling for you, turning guest requests into revenue opportunities.
Partnerships and Affiliate Programs
Connect with local tour operators and experience providers who handle the communication with the guests. You advertise their services and earn a commission - no need to manage or coordinate details - pure passive income.
Implementation Tips
✔️ Don't wait for guests to ask - have options ready and visible from the start.
✔️ Create a digital “add-ons menu” guests can browse anytime. This cuts communication and captures revenue.
Myth 3: Guest Experience, or “Luxury Properties Don’t Upsell”
🙅🏾 "I manage luxury properties with free amenities. Charging extra would lead to one-star reviews."
Reality Check
High-end hotels offer premium add-ons regularly. Upsells, when presented well, enhance the luxury experience with personalization, like private chefs or exclusive local experiences.
Adding Value, Not Nickel-and-Diming
A recent Beyond survey showed that 80% of guests are willing to pay for quality amenities and better locations. Proactively offering relevant services boosts satisfaction by fulfilling guest needs.
Luxury is About Options
True luxury means exceptional experiences, like helicopter tours or private chefs. Match your service level to guest expectations.
Implementation Tips
✔️ Tailor Amenities. Align offerings to guest profiles - business travelers may prefer workspace amenities, while leisure tourists might enjoy local experiences.
✔️ Go beyond basic amenities. Offer memorable experiences that match your property's style - like premium airport transfers for luxury stays or local wine tastings for boutique properties. The goal is to enhance, not exploit.
Myth 4. Payments and Accounting, or “The Accounting Nightmare Myth”
🙅🏻 "Each month we send owners their earnings. How do I manage the accounting for upsells without tracking it manually?"
Reality Check
Service-based upsells like concierge offerings generate revenue that’s 100% yours—no owner split. For operational upsells (e.g., early check-ins), decide whether to share revenue; it’s your team doing the work.
Clear Revenue Classification
Upsells are your direct revenue stream, separate from property management trust funds. These are value-added services you provide as a business owner. Think of it as your concierge service division, not part of the traditional property management scope.
Different Business Line
Upsell services represent an additional revenue stream, distinct from rental income. This is about expanding your business model beyond basic property management. You're operating as a service provider, creating new value for your guests.
Implementation Tips
✔️ Treat upsells as business revenue, not trust accounting.
✔️ See upsells as part of your service offering, growing your revenue without complicating accounting.
Myth 5. Uncertain ROI, or “The Not Worth It Myth”
🙅 "I don't think it would be worth the effort. I don't see that I would even break even."
Reality Check
The revenue potential from upsells significantly outweighs the setup effort. With automation and intuitive user experience, designed on the best practices of e-commerce, the ongoing management effort is minimal. Each property in your portfolio becomes an additional revenue generator.
Our data shows properties averaging $200 additional revenue per booking through strategic upsells. With automation handling the heavy lifting, it's pure profit.
Implementation Tip
Location, listing count, and available add-ons directly impact potential earnings. Calculate your property's revenue potential with our ROI calculator.
Don't take our word for it - just look at GoodNight Premium Stays in Phoenix. Within their first 6 months of implementing automated upsells through Enso Connect, they generated $250,000 in add-on revenue. Learn how they did it.
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