Payment automation for short-term rentals: simplify payment management and impress your guests

But with CiaoBooking's payment automation feature, everything changes: no more manual entries, no more follow-up calls for payments, and no more inconsistent payment timelines.

Our new Payment Automation module integrates seamlessly with the platform, sending personalized payment links, managing multiple automatic attempts, and centralizing every transaction in a single live dashboard. With just a few clicks, you can ensure PCI-DSS security and PSD2 compliance, reduce missed payments, and provide your guests with a smooth booking and stay experience.

In this article, you’ll discover how it works, the benefits for your business, and best practices for maximizing its potential.

The challenges of manual payment management in short-term rentals

In your short-term rental business, managing payments without an automated system can turn into a daily nightmare.

Here are the four main issues with non-automated payment management:

1. Human error and slow processes

Every time you manually enter a card number or type in an expiration date, you increase the chances of typos and transaction failures. Human error in payment management leads to longer reconciliation times and requires multiple checks, slowing down the entire payment process.

2. Missed payments and fragmented cash flow

Without automatic reminders, email or SMS notifications, and an intelligent retry mechanism, many guests may “forget” to pay on time. The result? Missed payments pile up, and your cash flow becomes unpredictable, with liquidity spikes followed by dry periods. A PMS without integrated payment solutions leaves your revenue too exposed to delays and payment gaps.

3. Friction at check-in/check-out

Without an automatic payment link, the front desk becomes a place of endless waiting and follow-up calls. Guests arriving late after a long journey may be greeted with tedious check-in procedures, negatively impacting their overall experience.

4. Compliance with regulations (PCI-DSS, PSD2)

Meeting the security requirements for card data (PCI-DSS) and Strong Customer Authentication (PSD2 SCA) is mandatory for anyone processing online payments. Without direct integration with certified solutions, you risk facing hefty fines and losing guest trust.

What are PCI-DSS and PSD2?

PCI-DSS (Payment Card Industry Data Security Standard)

An international standard created by the leading payment card networks (Visa, MasterCard, American Express, etc.) to protect sensitive credit and debit card data. It includes 12 fundamental requirements—from end-to-end encryption and network segmentation to strict account and privilege management, regular testing, and audits—that every business must meet to store, process, or transmit payment information securely.

PSD2 (Revised Payment Services Directive)

A European directive on payment service regulation, which came into effect in 2018. Its primary goal is to enhance the security of online transactions through Strong Customer Authentication (SCA)—two-factor authentication—and promote innovation by allowing authorized third parties to access users’ bank accounts (with their consent) to offer new payment and aggregation services.

In the next section, we'll show you how CiaoBooking’s Payment Automation transforms payment management into a smooth, secure, and fully automated process.

What is Payment Automation by CiaoBooking?

Payment Automation by CiaoBooking is the native module of the PMS for managing and automating payments. In simple terms, there is no longer any need to rely on external gateways or manual processes – everything happens directly within the platform you already use for reservations.

The system connects in real-time to your booking engine and accounting management software, synchronizing reservations, rates, and cancellation policies. Every transaction is automatically tracked, eliminating duplicate entries and discrepancies between front-office and back-office.

Thanks to tokenization and intelligent retry mechanisms, human error is eliminated: no more copying and pasting card numbers or managing reminders in Excel sheets. Payments are processed in seconds, without interruptions, and with instant notifications for both you and your guests.

What are the tangible benefits for your revenue and guest experience?

• More stable revenue: Reduced missed payments and predictable cash flow.
• Higher conversion rate: Simple, mobile-friendly payment links increase confirmation rates.
• Happier guests: Smooth check-in and check-out with zero waiting time at reception.

Key Features of the Payment Automation Module

Payment Automation by CiaoBooking is designed to intelligently connect every aspect of the payment process, eliminating bottlenecks and providing full visibility on every transaction. Here’s how it works:

1. Operational Simplification

No need to manually initiate every single transaction: the system automatically processes payments based on rules you set – deposits, balances, and penalties are applied automatically at the right time. Dynamic policies for cancellations and no-shows can be configured with just a few clicks, fully integrated with the booking engine, avoiding the need to manually manage exceptions.

2. Reduced missed payments

Automatic payment reminders are sent via email, SMS, or push notification, scheduled at the times and formats you prefer, reminding guests to pay before arrival. If the first attempt fails, the "last attempt strategy" takes over: the system retries multiple times, drastically increasing the success rate and reducing delays that disrupt cash flow.

3. Seamless payment experience

Every guest receives a responsive pay-by-link, perfectly suited for use on smartphones and tablets. At check-in and check-out, waiting times are drastically reduced: payments are already processed in advance, ensuring a smooth and professional welcome – or farewell.

4. Compliance and security

You don’t have to worry about implementing PCI-DSS hotel compliance on your own: tokenization and end-to-end encryption are managed natively. At the same time, being PSD2 & SCA ready ensures that all online payments comply with strong authentication, with automatic exemptions for recurring or low-value payments without complicating the user experience.

5. Control and transparency

The transaction dashboard provides a single real-time control panel: you can instantly view payments, refunds, pending payments, and performance metrics. Filters by property, period, and sales channel help you quickly identify any anomalies. Additionally, direct integration with the accounting module makes monthly reconciliation a breeze, eliminating double entries in financial systems.

With these features, CiaoBooking transforms payment management into a streamlined, secure, and results-oriented process, freeing you and your team from operational burdens while ensuring a memorable guest experience.

How Payment Automation Works: Step-by-Step

Let's take a look at the operational workflow of Payment Automation, from booking to check-out, to understand how you can optimize every stage.

Integrated with the Booking Engine: As soon as you confirm a booking—whether it comes through an OTA, direct channel, or call center—the Payment Automation module receives the details in real time: amount due, cancellation policy, and payment deadlines. Based on the rules you set (immediate deposit, balance X days before arrival, penalties), the system automatically schedules the first payment attempt or sends the payment link.

Pay by Link (3DS): For all non-refundable bookings, the guest receives a pay-by-link via email and/or SMS. The link is mobile-optimized and triggers Strong Customer Authentication (3D Secure) if required by PSD2 SCA. Once the payment is completed, the guest receives an instant confirmation, and your PMS records the transaction without any manual intervention.

Self Check-in with Automatic Payment: If you use the self check-in module, the system can block the delivery of access credentials (smart lock code, app PIN) until the payment is completed. This way, the guest can enter the property only after paying, eliminating no-show risks and ensuring operational security.

Phone Management and MOTO Fallback: If an online payment fails and the guest prefers to confirm by phone, the module supports MOTO (Mail Order/Telephone Order) mode: you enter the card details directly into the secure dashboard, and the system still applies end-to-end tokenization. If errors persist, the last attempt strategy kicks in, scheduling additional attempts with customized timing.

Automatic Reconciliation and Reporting: All transactions—successful, refunded, and failed attempts—are instantly available in the PMS transaction dashboard. With daily and weekly reports, you can export data to your accounting software or analyze it to optimize rates and payment policies.

With this hands-off workflow, you transform every step—from booking to check-in—into a consistent, fast, and fully automated experience.

Best practices for making the most of Payment Automation

To get the most out of CiaoBooking's Payment Automation, treat it as a true ally in your daily work:

1. Turn reminders into conversations

Instead of always sending the same text, create a few variations of emails or messages – maybe with a touch of personality (“Hi Marco, your stay is coming up soon!”) – and alternate them to see which works best. You can also experiment with different timing to find out when messages get the best open rates.

2. Get familiar with the Dashboard

Spend 10-15 minutes each week browsing your dashboard: look at more than just revenue and payment percentages—also pay attention to subtle trends like the retry success rate. Share key insights in a short internal report: a small habit that helps you quickly spot a performance drop or a spike in last-minute bookings.

3. Build a proactive team

Don’t just explain the payment policies: involve your front desk and back-office teams in a real-life simulation. Let them face scenarios like “payment declined” or “no-show” and solve them using the MOTO module or automatic retries. A well-trained team knows how to communicate better with guests, avoiding misunderstandings and reducing support requests.

By following these best practices, automation becomes a strategic advantage: less stress for you, more on-time payments, and happy guests who enjoy a seamless experience.

With Payment Automation by CiaoBooking, every step of the payment cycle becomes a smooth, secure, and error-proof process.

Ready to take your property to the next level?

Request a free demo or contact our support team to see how you can start using the Payment Automation module right away.