Maximize Revenue with Smarter Vacation Rental Upsells

Decorated vacation rental kitchen and dining room

Running a vacation rental business today means juggling more than bookings and calendars. Rising costs, fierce competition, and guest expectations have made it essential to find new ways to grow revenue and create memorable experiences. One of the smartest—and most overlooked—strategies is upselling.

In fact, a recent report from Enso Connect found that 82% of vacation rental businesses don’t currently offer upsells. That means operators who do offer upsells have an enormous opportunity to stand out, boost guest satisfaction, and drive revenue without raising nightly rates.

During our recent webinar with ChargeAutomation, Escapia experts shared how integrated upselling can transform property management operations. Here’s what professional vacation rental managers need to know.

Why Upselling Matters More Than Ever

Upselling isn’t new, but it’s never been more relevant. As Garrett B., marketing expert from Escapia, shared,

"Upsells should be a strategy you do alongside other marketing efforts. They help you get the most out of every single booking."

The benefits go beyond extra dollars:

  • Increase revenue without raising nightly rates
  • Delight guests with personalized add-ons
  • Stand out in a crowded market
  • Improve reviews - guests often remember thoughtful offers even if they don't buy

Even a simple offer, like early check-in or late checkout, can change how guests perceive their stay—and how much they spend.

The Escapia + ChargeAutomation Advantage

With Escapia’s vacation rental property management software seamlessly integrated with ChargeAutomation, upselling becomes simple, automated, and impactful:

  • Dynamic Upsells: Only available add-ons are shown, avoiding refunds and guest frustration.
  • Seamless Data Sync: Booking and guest data flow between Escapia and ChargeAutomation automatically, ensuring a smooth connection without disruptions.
  • Automated Timing: Offers appear at the right moment—before arrival, during the stay, or before departure.
  • Mobile-First Design: Guests view and purchase upsells directly from their phones.
  • Two-Way Sync: Payments, bookings, and upsells automatically flow into Escapia for accurate trust accounting.

Want to see these strategies in real time? Our recent webinar walks through how professional vacation rental managers are using Escapia to automate upsells, boost revenue, and deliver a satisfying guest experience.

Watch the full webinar

Real-World Upsell Success: Live Suites

One of the best examples of upselling in action comes from Live Suites. With a portfolio of 60 properties, they’ve turned upsells into a reliable and significant revenue stream by offering simple but valuable add-ons like early check-in, late checkout, and curated local experiences.

Here's the impact:

  • $150,000+ in additional revenue every year
  • $216 in extra revenue per booking
  • $40 per unit, per month across their portfolio

The takeaway: Even a few thoughtful upsells can add up to a major source of recurring revenue.

As Nick, hospitality expert from ChargeAutomation, explained,

"These aren't forced extras. They're services guests are delighted to purchase - offers that enhance their stay and improve reviews. It's a win-win."

What to Upsell (and When)

Successful upselling is all about relevance and timing

Before Arrival

  • Early check-in
  • Grocery delivery
  • Luxury welcome baskets
  • Airport transfers

During Stay

  • Spa treatments and massages
  • Private chefs
  • Local tours or boat rentals
  • Equipment rentals (bikes, paddleboards)

Before Departure

  • Late checkout
  • Pool passes or luggage storage
  • Future booking discounts

As Garrett B. pointed out, the value of upselling goes beyond the purchase itself:

"Even if a guest doesn't buy, the fact that you offered thoughtful options enhances their perception of your brand."

Avoiding Common Mistakes

Upselling works best when done thoughtfully:

  • Don't overhwelm guests with too many offers
  • Avoid manual tracking - automation ensures accuracy
  • Focus on timing; late offers often fall flat

With Escapia + ChargeAutomation, upselling feels natural, not pushy—and it saves teams hours of manual work.

Key Takeaways for Property Managers

  • Start simple: Early check-in, late checkout, grocery delivery
  • Automate with integration: Dynamic upsells reduce errors and refunds
  • Time it right: Match offers to the guest journey
  • Think mobile-first: Guests browse and buy on their phones
  • Build trust: Transparent upsells boost guest confidence and reviews

The Future of Upselling Is Here

Upselling is one of the most underused tools in vacation rental property management. With Escapia + ChargeAutomation, it becomes a seamless part of the guest journey, boosting revenue, improving satisfaction, and freeing managers from repetitive tasks.

Ready to see smarter upsells in action? Request a demo today and discover how Escapia helps you scale your vacation rental business.

Get a demo