TL;DR: Short-term rental upselling means offering paid add-ons like early check-in, late checkout, and local experiences that boost guest satisfaction and increase revenue per booking. This guide covers when to offer upsells, how to avoid sounding pushy, and which tools can help you scale the process.
Upselling can elevate both your guests’ vacation and your profits. More property managers are catching on to what hotels have known for decades: guests want options, and they’ll pay for the right ones.
Offering vacation rental upsells sets you apart from competitors while giving guests products and services that enhance and personalize their stay. That means higher rebooking rates, stronger reviews, and ancillary revenue beyond nightly rates. Your guests’ travel budget isn’t limited to rent — tap into it.
In this article we’ll cover:
- The best timing to offer upsells
- Ways to offer upsells without seeming pushy
- Practical tips and examples of upsells you can offer tomorrow
Are upselling and cross-selling the same thing?
In short-term rentals, upselling means encouraging guests to upgrade their existing booking (for example, late checkout or a higher-end unit). Cross-selling means offering add-ons that sit alongside the stay itself, like airport transfers, tours, or stocked fridges. Both increase average revenue per stay when done thoughtfully.
Here’s the breakdown:
Upselling focuses on upgrades within the same category:
- Premium unit with more space and better amenities
- Extended stay options
- Room or package upgrades
Cross-selling offers complementary products or services:
- Airport transfers and transportation
- Local tours and experiences
- Mid-stay cleaning or grocery delivery
- Equipment rentals (e-bikes, paddleboards)
Offering upsells without being too pushy
The difference between a welcome upsell and an annoying one comes down to three things:
- Personalize offers: Tailor options to specific guests rather than blasting everyone with the same list
- Time them right: Match offers to key moments in the guest journey
- Lead with value: Explain the benefit in guest-first language
There’s a fine line between helpful extras and sales spam. Approach upsells with a genuine focus on enhancing the stay, not extracting maximum dollars.
What this looks like in practice: Pushy means sending three upsell messages before arrival. Value-first means one clear message a week before check-in, offering airport pickup and early check-in for guests landing early in the morning.
When presenting upsell options, highlight what the guest gains — not what you’re selling.
The optimal timing for offering upsells
The right offer at the right time changes everything. Here’s when each timing window works best:
- Pre-booking: Showcase premium options and set your listings apart
- Pre-arrival: Guests have clarity on plans and are ready to lock in convenience services
- Upon arrival: High excitement, openness to upgrades
- During the stay: Target specific needs as they emerge
Pre-booking
Including upsell options during the initial booking process sets you apart immediately. On your direct site, offer early check-in and welcome hampers as optional add-ons in the checkout flow rather than burying them in post-booking emails.
At this point, consider offering: early check-in or late checkout, premium packages with welcome baskets, grocery delivery service, airport transfers, or access to exclusive amenities.
You may not see many guests buy at booking — the reservation itself is a big expense. But knowing these options exist makes your listings more attractive.
Pre-arrival
7 – 14 days before arrival is the sweet spot for upsells that weren’t purchased at booking. Now that guests are closer to arriving, they’re thinking practically: maybe they do want airport pickup, groceries waiting, or that early check-in after checking their flight times.
Upon arrival
Guests are excited and open to exploring additional offerings. At check-in, a QR code or in-room tablet can highlight “upgrade your stay” options like late checkout or a mid-stay clean. This touchpoint catches guests in discovery mode.
During the stay
Pay attention to guest signals and match offers accordingly:
- Families: Kids’ entertainment kits, local family experiences
- Remote workers: Late checkout, extra workspace amenities
- Longer stays: Mid-stay cleaning, linen refresh
Timing matters here. Don’t interrupt their experience or make them feel pressured. A friendly, non-intrusive suggestion works best.
Which upsells should I offer?
Based on data from upsell partners, here’s what guests actually buy:
- Late checkout (most popular)
- Early check-in
- Pet fees
Other high-performers include mid-stay cleaning, e-bikes and e-scooters, and stocked fridges.
Aim for at least one offer in each category so guests can choose between time-savers, comfort boosts, and unique experiences:
- Time-based: Early check-in, late checkout, flexible arrival
- Comfort: Mid-stay cleaning, stocked fridge, premium linens
- Experiences: Local tours, equipment rentals, private chef
- Fees: Pets, extra guests, parking
Portfolio thinking: A 40-unit coastal operator might lead with late checkout and early check-in across all units, then add e-bike rentals in beach towns and mid-stay cleaning for longer bookings. Match your upsell menu to your properties and guest profiles.
Upsell partners: Our top picks
Start by mapping where you want upsells to appear — tablet, SMS, email — and choose partners that match that journey and your portfolio size.
1. Duve
End-to-end guest management with strong upsell templates. Best for multi-property operators who want automation across messaging and upsells.
Duve connects you with third-party suppliers for services like breakfast in bed, spa packages, bike tours, and show tickets. Their built-in guest app handles communication in the guest’s native language, one-click upsell purchases, property information, and even keyless entry.
2. YourWelcome
In-property tablets that present upsells without intrusive texts or emails. Best for operators who want a physical touchpoint.
Property managers connect their payment provider and set up services on the tablet. Guests can request add-ons directly, and you accept or decline. YourWelcome’s dashboard lets you experiment with pricing and images while tracking click-through and conversion data.
Available in English, French, German, Spanish, Italian, Portuguese, Japanese, and Mandarin.
3. DACK
Smart guest platform with four upsell categories: digitally enabled, goods and services, local vendors, and pre-built third-party connections. Best for operators who want automation without extra manual work.
DACK sends targeted communications based on smart triggers — like when a guest first opens the door or when a unit goes vacant. The platform doubles as a digital concierge with customizable local recommendations.
Operates in the US, Mexico, Canada, UK, and Australia.
4. Enso Connect
Dynamic guest-facing web app (the “boarding pass”) that guides guests from booking to checkout. Best for operators who want upsells integrated throughout the entire guest journey.
The boarding pass includes verification, agreements, fees, available upsells, check-in instructions, lock codes, and property guides — all in one place. Operators can create custom upsells, integrate multiple Stripe accounts, and add affiliate links for services like Uber, OpenTable, and local providers.
Operates globally with 150+ language support.
5. Mount
Online marketplace for curated local experiences and stay enhancement add-ons. Best for smaller operators (20 properties or less) focused on e-bikes, paddleboards, and local experiences.
Guests access available experiences after booking and pay directly through the platform. Mount handles confirmation and instructions.
Primarily available in the United States.
6. GuestView Guide
Interactive wall-mounted digital concierge. Best for operators who want high-visibility, in-property upsell displays.
The slideshow feature displays tailored offers based on each guest. Payment goes through the guest’s mobile device. Strategic placement keeps upsells visible rather than buried in forgotten emails or apps.
Currently serves vacation rentals in the United States, Puerto Rico, and U.S. Virgin Islands.
Getting started with upselling
Incorporating upsells doesn’t have to be overwhelming. Here’s your action plan:
- Define three core upsells: Start with early check-in, late checkout, and one local experience or convenience service
- Choose one or two channels: Pick a partner tool that matches your guest journey and portfolio size
- Measure for 60–90 days: Track extra revenue per stay before expanding your upsell menu
Even a few well-designed vacation rental upsells can lift ancillary revenue and average revenue per stay without adding new properties.
FAQ
Not if they’re relevant, optional, and limited to a few well-timed offers that focus on making the stay better. Personalization and timing matter more than volume.
Results vary by market and property type, but operators commonly report increased revenue per booking from a basic upsell menu.
Focus on guest signals: families benefit from equipment rentals, remote workers value late checkout, and longer-stay guests appreciate mid-stay cleaning. Match offers to needs rather than blasting everyone.
You can start manually with well-timed emails, but dedicated tools automate the process, track conversions, and scale with your portfolio. Most operators find the ROI justifies the investment once they’re beyond 10–15 units.
Guesty’s talented marketing team is comprised of passionate professionals who share insightful industry knowledge and shape brand narratives. By bringing a diverse blend of expertise to the table, we are the visionary architects behind the Guesty brand and innovative campaigns that help people understand our product.
