How to Manage Multiple Vacation Rentals without Losing Your Sanity

Mar 15 2023

Get tips on how to use Hostfully to optimize your vacation rental business and make more profit.


What’s in this article?

More turnovers, complicated cleaning schedules, and constant guest questions are just a few of the typical stresses of managing multiple properties. But what if we told you it’s possible to run more units without it impacting your day-to-day… 

Having more properties doesn’t have to create more work. And while managing multiple short-term rentals presents its challenges, there are tried and trusted strategies for making it more manageable, like: 

  • Using a robust PMS
  • Building an integrated tech stack
  • Having scalable, repeatable processes
  • Automating wherever possible
  • Investing in smart technology
  • Sharing digital guidebooks
  • Using task management tools

Take a look at our overview of the challenges and solutions to managing multiple short-term rentals so you can keep guests happy and maintain your sanity. 

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Top challenges with managing multiple short-term rental properties

You aren’t alone—practically every short-term rental manager juggling multiple properties faces challenges, especially when they’re just starting to grow. In our 2022 Vacation Rental Industry & Hospitality Report, we spoke with hundreds of vacation rental operators around the globe. Here’s what they’re struggling with. 

Pie chart showing challenges faced by vacation rental companies in 2022
From technology to general operations, vacation rental managers around the world face similar challenges.
Source: Hostfully 2022 Vacation Rental Industry & Hospitality Report


You see that big blue piece of the pie chart, right? Technology is the primary challenge facing vacation rental managers today, with over a third of survey respondents stating it’s a struggle for them. 

When you get even more granular, you can see that the specific aspects of technology that cause frustration are: 

  • Automation
  • Pricing
  • Calendar sync and booking management
  • Integrations
  • Accounting
  • Centralization
Pie chart showing tech challenges faced by vacation rental companies in 2022
Automation and pricing are the most significant tech struggles that vacation rental operators faced in 2022.
Source: Hostfully 2022 Vacation Rental Industry & Hospitality Report

Cleaning and turnover 

Cleaning and turnover were also cited as significant vacation rental management challenges among property managers. When running multiple units, it can be difficult to keep track of check-in and check-out dates, cleaning schedules, and maintenance issues, and this task just gets more challenging the more properties you acquire. 

Hiring and staffing

Having more properties means you need more people-power, but hiring and staffing presents challenges for vacation rental managers with multiple units. 

To begin, persisting labor shortages in the hospitality industry make it hard to find employees that stick around. And finding the right balance between having enough staff to run all your properties without overstaffing during the off-season can be a real struggle. 


When you’re just getting started, you probably rely on Airbnb, Vrbo, or to bring in reservations. But as you grow, building out a direct booking strategy is key to developing a sustainable business, which is why marketing becomes increasingly important the more properties you manage. 

Guest expectations and communications  

Communicating with one guest at a time is one thing—juggling guest questions while exceeding expectations for even just a handful of units is a different story. As you get more simultaneous bookings, communicating with guests and giving them an exceptional stay gets harder and harder. Unless you practice all our tips below.  

How to successfully manage multiple vacation rentals

Enough doom and gloom—you can (and will!) successfully manage multiple vacation rentals. Follow these steps to stay sane while managing multiple vacation rentals, as well as scale your business even more. 

Use a PMS 

In our report, over a third of vacation rental managers cited their property management system (PMS) as the most valuable piece of software in their tech stack. And this software becomes more vital the more rentals people manage, with 63% of companies with between 25 and 49 properties reporting their PMS as their most important tool.

Pie chart showing the most valuable type of software used by vacation rental managers in 2022
Your PMS can be your most powerful tool if you choose one that works for your business.
Source: Hostfully 2022 Vacation Rental Industry & Hospitality Report

A PMS lets you manage key tasks that become increasingly challenging as you expand your portfolio, like accounting, guest messaging, and owner management. Take a look at just a few ways a PMS can help you as you scale your business: 

  • Channel management: By using a property management platform (PMP), you know your calendars are updated across all the OTAs you use. For example, Hostfully integrates with over 20 popular listing sites, meaning there’s no need to pay for a separate channel manager to keep track of all your reservations and prevent double bookings. 
  • Marketing: Keeping track of day-to-day operations is hard enough when you manage multiple properties, so marketing may end up taking a backseat. But a PMP like Hostfully allows you to build a direct booking website or embed a booking widget on your existing website, making it easy for guests to book direct. 
  • Guest messaging: Use a PMP that allows you to schedule messages and view all your messages in a centralized inbox. Hostfully, lets you message guests via SMS, Whatsapp, or whichever booking sites you use, so you can communicate with all your guests from one convenient location. 
  • Owner management: Chances are the more properties you operate, the more owners you interact with. Using a PMP lets you quickly generate reports to share with owners, and Hostully even allows you to schedule data exports and automatically send them to owners at the time and date you set.
  • Accounting: The more profits and expenses you have, the harder it gets to keep track of finances. A PMP like Hostfully will integrate with your existing accounting software, letting you connect every reservation that comes in to your bookkeeping tool.

The benefits of using a PMS are endless, and the more your vacation rental business grows, the more valuable this software will become. There are tons of PMS options out there, like Hostfully, Guesty, and other alternatives, so make a list of what features are most important for you to guide your decision-making and ensure you choose the right one. 

Build an integrated tech stack

A PMS isn’t the only tool you’re going to need to manage numerous vacation rentals. Our survey respondents also cited dynamic pricing tools, guest communication platforms, and productivity solutions as essential software in their tech stack.

But to make these tools work for you without causing more chaos, you need to choose a PMP that offers extensive integration options. In the case of Hostfully, we offer over 60 integrations, from accounting and channel management to marketing automation and dynamic pricing. 

With an integrated tech stack, you can simplify your role as operations manager to better focus on growing your portfolio. 

Have scalable, repeatable processes 

Large-scale vacation rental property management relies on dependable processes. By building out repeatable processes that can grow with you, you prepare yourself for the unexpected, from sudden staffing changes to a full booking calendar during the off-season. 

Some examples of ways you can create processes that support business growth include:

So before you have too many properties to manage, focus on building strong, scalable processes that can grow with you, no matter how many property owners you work with and vacation homes you manage. 

Automate wherever possible

If there’s one golden rule for managing multiple properties, it’s automate, automate, automate. Automation can save you hours of time per week, meaning you don’t even have to think about those time-consuming recurring tasks that you would otherwise have to find time for in your busy schedule.

Image showing automation triggers and templates with the Hostfully PMP
Set triggers and design custom message templates with Hostfully’s PMP to cut down on repetitive tasks.
Source: Hostfully

You can automate in so many areas of your business, including: 

Turnover management

Specialized cleaning software can help you streamline turnovers and ensure you never miss a clean. Hostfully integrates with tools like Breezeway, EZCare, Operto Teams, Properly, and TurnoverBnB, which help you automate cleaning schedules and track task status. 

Dynamic pricing

You can spend hours analyzing pricing models, or you can trust the specialized tools. Hostfully offers integrations with Beyond, DPGO, Nightpricer, PriceLabs, Rented, and Wheelhouse so you can be sure all your listings are automatically updated with fully optimized rates. 

Guest communication

Guest messages can be a huge time drain, so automating as many communication tasks as possible gives you back your free time. Create template messages (yes, you can do this with Hostfully, too), which can help you automate up to 70% of your guest messages.  

Payment processing

Instead of spending hours a week on invoicing and following up on payments, automate this process. That means no more manually processing security deposit reception and refunds. And you can use property management software that works with PayPal, Stripe, and VacationRentPayment to keep collecting payments with no extra work, irrespective of how many bookings are coming in. 

Review management

By creating a messaging template, you can automatically request reviews from guests once they check out. Because reviews are such a big part of your success, this automation saves you time and wins you more five-star ratings. 

Invest in smart technology

When you just manage one short-term rental, you may be able to meet each guest upon arrival. But when you run dozens of property listings, this not only becomes incredibly stressful, but sometimes it’s also impossible. 

Tech solutions like smart locks, noise monitoring devices, energy-saving devices, and home automation tools make it easier to remotely manage and monitor multiple properties. Smart locks, for example, enable you to offer self-check-in, which guests love and can save you significant time and staffing expenses. 

And noise monitoring devices give you real-time data about noise levels at your properties, so you can get updates from in-home devices if your guests are causing a ruckus.  

Just make sure your smart technology integrates with your vacation rental management software so it doesn’t cause you extra work. Hostfully, for example, integrates with smart home solutions like Jervis System, Lynx, Minut, NoiseAware, Ok2Charge, Operto, PointCentral, and RemoteLock. 

Share digital guidebooks

While messaging templates can help you cut back on guest communication, digital guidebooks can be another great resource. By sending out digital guidebooks, you proactively provide guests with all the information and details they need so they don’t have to constantly be reaching out to you about where to park or how to use the coffee maker. 

Plus, you can include a curated local guide, which showcases your restaurant recommendations and tips on what to do in the area. This adds a special touch to your guest’s experience, making their stay unique and memorable. 

The more properties you manage, the harder it gets to make each guest’s stay feel personalized. Digital guidebooks make it possible to give guests a special vacation without spending all your free time responding to questions about the best places to eat in town. 

Hostfully Digital Guidebook showing local dining recommendations
Reduce the number of guest questions coming in by giving them all the answers in a customized guidebook.
Source: Hostfully

Don’t be afraid to delegate

The sooner you accept you can’t do it all on your own, the better. And especially if you got started as a solo operation, it can be hard to let go of certain parts of your business. 

But hiring people you trust and delegating time-consuming tasks lets you focus on bigger-picture ideas instead of being stuck in your day-to-day, and that’s the only way to get the time and space you need to be able to scale. 

Consider this when choosing whether self-hosting using automation or outsourcing to a rental management company is right for you. While it might be tempting to hand over the keys to a big property management company, just know you can definitely run a short-term rental business without losing your sanity with the right mix of delegation and automation. 

Manage more properties with less stress

A bigger portfolio doesn’t have to mean less free time. With the right approach and tools, you can keep growing your business without it dominating all your waking hours. The key is to identify where you can automate, where you can delegate, and what you need to prioritize. 

And when you use the right tools, like a powerful PMP, a standout vacation rental website, and specialized vacation rental software, you can trust that your guests and business are being taken care of without losing any sleep. 

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