How to start a property management business: practical guide & essential tools

In recent years, the property management sector has grown significantly in Europe. More and more hosts and investors are turning to professionals to manage their vacation rentals or short-term apartments—people who can handle everything from bookings and communication to cleaning, payments, and paperwork.

It’s a real opportunity for anyone who wants to build a business in the hospitality industry—provided you start off on the right foot.

But where should you begin?

The truth is, managing even just two or three properties takes more organization than it seems. It’s not enough to list your property online or answer the phone: you need structure, know-how, and—most importantly—the right tools to stay in control (without losing your mind).

In this article, we’ll look at how to take your first steps into property management, what everyday challenges you’ll face, and why using a Property Management System (PMS) like Ciaobooking from the beginning can make all the difference.

What is property management (and why it’s a real opportunity right now)

In hospitality, property management means taking care of both the day-to-day operations and the long-term strategy for one or more accommodations—whether it’s apartments, vacation rentals, B&Bs, or small hotels. A property manager can be an individual professional, a company, or a specialized agency tasked with managing every aspect of guest hospitality: from publishing listings on OTAs (like Airbnb or Booking.com) to handling cleanings, guest communication, and local administrative requirements.

Why becoming a property manager in 2025 is still a great opportunity

Here are just a few reasons why launching a property management business in 2025 remains a smart move:

Growth in experiential and decentralized tourism

In recent years, the demand for stays in apartments or private homes has grown significantly. More and more travelers are seeking flexible, authentic, and personalized experiences compared to traditional hotel offerings.

Increase in second homes and real estate investments

Many second-home owners are looking for professional support to rent out their properties without managing them directly. That’s where the property manager comes in.

Industry digitalization

Today, it’s possible to manage multiple properties remotely thanks to digital tools that automate many day-to-day tasks. This makes property management a scalable and sustainable business, even for those just getting started.

Operational flexibility and room for specialization

You can choose to focus only on operational tasks (cleaning, check-in) or also take care of strategic areas (OTA management, pricing, marketing). Whether you manage a few high-end apartments or build a larger portfolio, the path is yours to shape.

The daily challenges of a property manager (and how to handle them)

Starting a property management business is full of potential, but also full of complexity. As the number of units grows, so does the operational puzzle. Here are some of the key challenges you may face:

1. Coordinating bookings, cleanings, and check-ins

Each booking triggers a chain of actions: cleanings, guest reception, messages, and sometimes maintenance. Without a centralized system, errors and scheduling conflicts are likely.

A Property Management System (PMS) lets you automate the coordination between calendars, cleaning staff, check-in procedures, and guest communication, reducing operational stress.

2. Managing your online presence

Being listed on multiple booking platforms is key to visibility, but it also means constantly updating availability, rates, and policies across all channels.

A PMS with an integrated channel manager allows you to sync everything with one click, preventing overbookings and inconsistencies.

3. Communicating with guests

Every stay involves dozens of messages: questions, check-in instructions, reminders, reviews. Managing all of this manually can become overwhelming.

Advanced PMS platforms let you automate replies, schedule pre- and post-stay communications, and simplify guest relations without compromising on quality.

4. Legal and tax compliance

Uploading guest data to authorities, submitting statistics, issuing electronic invoices... every property manager has to meet a number of bureaucratic obligations.

A PMS designed for the local market includes all the necessary features to handle compliance properly, without relying on external tools.

Why you should start using a PMS from day one (even if you manage just a few properties)

Many still believe that a property management system is only needed once you hit a certain number of apartments or bookings. In reality, using professional tools from the beginning can be the difference between smooth growth and chaotic management.

Here’s why it’s a smart move right from the start:

1. Build scalable processes

If you're managing two apartments, Excel and WhatsApp might be enough. But what if tomorrow it’s five? And ten the day after? A PMS helps you set up organized, repeatable workflows that are ready to scale.

2. Minimize operational errors

Even with a small number of units, a single mistake can be costly—an overbooking, a forgotten message, a missed communication. Automating repetitive tasks protects you from slip-ups and wasted time.

3. Offer a truly professional experience

Today’s guests expect the same ease and reliability from vacation rentals as they do from hotels. A PMS helps you deliver a smoother, more personalized experience, which leads to better reviews and repeat bookings.

4. Keep everything under control

Having a clear, real-time overview of your bookings, payments, sales channels, and performance helps you make informed decisions and build a solid foundation for your business.

A PMS isn’t a cost—it’s an investment. It simplifies your work, improves your service quality, and helps your business grow. And with vertical solutions like Ciaobooking, tailored for the hospitality industry, getting started is easier than ever.

How to choose the right PMS for your business

Not all property management software is created equal. You need a tool designed specifically for the needs of hospitality professionals—and one that can grow with your business. So how do you choose the right one?

Here are some key criteria to look for:

1. Is it designed for your industry?

Avoid generic software. A good PMS for property managers should be built to handle apartments, B&Bs, and vacation rentals, with features tailored to short-term stays, flexible check-ins, and OTA synchronization.

Ciaobooking was created exactly for this: to simplify life for those managing hospitality businesses, including multi-location and multi-owner properties.

2. Does it support automation of daily tasks?

A truly effective PMS helps you save time every day. Make sure it allows you to:

• Automate guest messaging
• Manage digital check-ins and send data to local authorities
• Generate and send receipts/invoices electronically
• Sync calendars with top OTAs (Booking, Airbnb…)

3. Does it give you a clear view of your data?

Access to updated reports and performance stats is key to making smart decisions. A good PMS shows you the numbers that matter—clearly and simply—even if you’re not a data expert.

4. Is it easy to use, even for beginners?

Especially if you’re just getting started, you need a tool that’s simple, intuitive, and offers reliable support. Ciaobooking, for example, provides support in English, a clear interface, and a team that understands your workflow.

5. Is it compliant with regulations?

From check-ins and reporting to electronic invoicing, your PMS should stay up to date and fully compliant with all local laws.

Organization, efficiency, and growth start with the right tools

Launching a property management business takes planning, the right mindset, and the right software. And the PMS you choose can mean the difference between a chaotic operation and a smooth, scalable, professional workflow.

With a PMS like Ciaobooking, you can:

• Automate everyday operations
• Avoid administrative mistakes
• Deliver a better guest experience
• Track your business with real-time data
• And grow sustainably
  

Whether you're just getting started or already scaling up, building a strong digital foundation is the first step toward working smarter—not harder.

Want to see how Ciaobooking can help you manage your properties?

Book a free demo and start building a solid, professional business right from day one.