A recent KeyData survey revealed a fascinating trend for 2025. 77% will focus on pricing optimization. While 74% of property managers plan to add more properties, only 33% are considering upsells.
Let’s pause here. Adding properties means multiplying your workload—more maintenance, guest communications, owner relationships, and everything else. 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 additional income from rental homes you already manage, without the complexity of securing new properties or managing more owner relationships.
In the previous article, we explored the untapped potential of upsells and the revenue boost they can bring. Today, we’ll address the elephant in the room. Why are only 33% of managers planning to leverage upsells in 2025? And why does the majority still focus on the more labor-intensive path of adding inventory? We’ll debunk the top 5 myths holding businesses back from this revenue opportunity.
In our conversations with property managers, we often hear concerns about implementing upsells. Time and again, we’ve watched a larger group of skeptical property managers transform into upsell advocates. After implementation, they often tell us, “We wish we’d started sooner!” We distilled these top 5 myths that keep vacation rental businesses from unlocking this additional revenue stream. In this article, we’ll discuss these obstacles and explore why the reality is often far different from common assumptions.
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
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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.
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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.
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Practical Implementation Tips
When you receive an early check-in or late checkout request, here’s your simple checklist:
Q: Do you need to accept the early check-in right away?
A: No, you can wait until you have better visibility of your schedule.
Q: Can you accept closer to the check-in date?
A: Yes, this gives you time to coordinate with your cleaning team and ensure everything is ready.
Q: Can you take a credit card imprint to automatically charge it when accepted?
A: Absolutely – this secures the booking while giving you flexibility in timing.
Q: How will you communicate availability to the guest?
A: Set up automated notifications through your property management system.
2. Guest Communication or The “Fewer Touchpoints is Better” Myth
”"No add-ons here. I'm certainly not looking for any more reasons to deal with the guests."
Reality Check
Strategic upsells actually reduce guest messages by anticipating and automatically fulfilling common requests. Plus, guests appreciate having options at their fingertips.
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Proactive vs. Reactive Approach
By setting up your upsell offerings in advance, you transform multiple back-and-forth conversations into simple one-click approvals
Being proactive means your system does the selling for you, turning guest requests into automatic revenue opportunities
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Partnerships and Affiliate Programs
Connect with local tour operators and experience providers who handle the communication with the guests.
You simply advertise their services and earn a commission – no need to manage bookings or coordinate details. This creates passive income while service providers handle the guest interaction
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Practical Implementation Tips
Here’s how to minimize work while maximizing revenue:
Q: Are you being proactive or reactive?
A: Being proactive by setting up automated offers means less work later. Don’t wait for guests to ask – have options ready and visible from the start.
Q: Are you asking the guest if they want something?
A: Instead of initiating conversations, let your system showcase available options automatically at key booking moments. This transforms manual outreach into passive opportunities.
Q: Are you presenting them with a menu of offers they can choose from?
A: Create a digital “service menu” that guests can browse and book on their own time. This eliminates the need for back-and-forth communication while capturing revenue opportunities.
3. Guest Experience Impact or The “Luxury Properties Don’t Upsell” Myth
”"I manage luxury properties with free amenities. I couldn't imagine nickel and diming my guests - that would just lead to one-star reviews."
Reality Check
High-end hotels consistently offer premium add-ons. When presented properly, upsells enhance the luxury experience by offering personalization. Think private chef services, luxury airport transfers, or exclusive local experiences.
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Value-Added Services, Not Nickel-and-Diming
The recent Beyond’s survey showed that 80% of guests surveyed aren’t just looking for the cheapest rate—they’re willing to pay for quality amenities and a better location. Proactively offering relevant services actually improves guest satisfaction. It’s about anticipating and fulfilling guest needs, not charging for basic amenities. When you provide services guests are already seeking, you enhance their stay while driving revenue.
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Luxury is About Options
True luxury isn’t just about free toiletries – it’s about access to exceptional experiences. Whether it’s a helicopter tour or a private chef, premium guests expect premium options. The key is matching the service level to your property segment and guest expectations.
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Practical Implementation Tips
Here’s how to enhance guest experience through strategic upsells:
Q: Are you providing amenities that can be tailored to each individual or their experience?
A: Consider your guest profiles – business travelers might value early check-in and workspace amenities, while leisure travelers might prefer local experiences and late checkout. Customize your offerings accordingly.
Q: How are you leveraging upsells to enhance guest experience?
A: Think beyond basic amenities. Offer memorable experiences that align with your property’s positioning – from premium airport transfers for luxury properties to local wine tastings for boutique stays. The goal is to enhance, not exploit.
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 typically generate revenue that’s 100% yours – no owner split required. For operational upsells like early check-in or late checkout, you can decide whether to share this revenue, considering it’s your team handling the extra work.
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Understanding 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.
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Business Line Differentiation
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 and your business.
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Practical Implementation Tips
Here’s how to properly structure upsells in your hospitality business:
Q: Is this trust accounting or a service you offer?
A: This is your service offering, not trust accounting. You’re providing and managing these services directly – from early check-ins to local experiences. These are business revenues, not held funds.
Q: A separate business line or a product offering in your business?
A: Consider this a product extension of your existing business. Just as hotels offer room service and concierge services, you’re expanding your revenue streams through guest services. This is about growing your business model, not complicating your trust accounting.
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
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Understanding Return on Investment
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.
But 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 pure profit. Learn how they did it.
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Practical Implementation Tips: Data-Driven Decision
Location, listing count, and available additional services directly impact potential earnings. Calculate your properties’ revenue potential with our ROI calculator.
Final Thoughts
Upselling in vacation rentals isn’t just about adding extra revenue—it’s about enhancing the guest experience and optimizing existing resources. It’s also about creating meaningful touchpoints that differentiate your property within the realities of vacation rentals. By breaking down the top myths around upsells, we hope to shift the conversation from “why not” to “why haven’t we started sooner?” When done strategically, upsells can deliver value across the board: guests appreciate the tailored options, property managers unlock new revenue streams, and teams work more efficiently through automation. So as you consider growth for the coming year, remember—sometimes the biggest wins are in the properties you already manage. Embrace upselling as a tool for both revenue growth and guest satisfaction and get ready to see results that make an impact.
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