Your short-term rental business isn't there to weigh you down or give you another job. It's there to help you break free. But if you aren't getting results, you're never breaking free. And increasingly, the gap between operators who see strong returns and those who struggle comes down to one thing: data
Not just having data, but protecting it, understanding it, and using it to power the systems that drive direct bookings, repeat guests, and sustainable growth.
Here's a statistic that should concern every operator: the average person spends about 18 months with their property management system. That's not a long time. And every new setup comes with a very real problem: losing all of your historical data.
You might get some data from Airbnb when you sync your new PMS, but everything to do with direct bookings, historical prices, and contact information can get lost in those transitions. This is the stuff that's really important to you as an operator. It's the foundation of your business intelligence.
The smartest move you can make right now is to export data from your property management system and back it up. Whatever happens, whether you switch systems, something goes down, or data gets lost, you need your own copy and your own records of every guest transaction, every reservation, and every piece of contact information.
You never know when that information might be useful in the future. And you never know what might happen to it if you decide to switch software or PMS vendors. Having your own backup is probably one of the most valuable habits you can develop. It doesn't need to be every week or even every month. Every quarter, just do a backup and get it all into a CSV or JSON file. Put it on Google Drive as a big spreadsheet. Make it yours.
The first layer of good data management is good data collection. Property management systems can collect quite a bit. Marketing systems can collect quite a bit. Platforms like Airbnb can collect quite a bit. But the first thing you need to do as an operator is make sure that every opportunity you have to add information into the systems you're using, you take it.
Ask the question: why is somebody traveling? What kind of amenities are they interested in? Note whether they booked six months before arrival or one month before arrival. Every possible data point is valuable down the road. The penalty for collecting it is really low, and the return on collecting it is really, really high.
We are now in an era where intelligence is almost free. The old world, the pre-AI world, had a limit on what you could do with data. It was limited by the people who were looking at it and responding to it. If you're dealing with clogged toilets and burst pipes, you can't worry about why someone came or how early they booked. You just want to make sure the house is okay when they arrive.
We are no longer in that world. There is intelligence available to deal with all of that information such that you can use it for better messaging, better marketing, and better guest experiences. So collect all that data, and then find the systems that can turn it into quality guest experiences down the road.
Even before plugging your data into sophisticated systems, you can upload it to tools like ChatGPT, Claude, and Gemini and ask questions about your business that are otherwise hard to get insight into. Who are my best guests? Find me the people that left five-star reviews and find commonality between all those people. Do they book in the summer? Do they book last minute? Do they book well ahead of time? Are they families? Are they couples?
Having that data and being able to use what you might call level-zero tools, the most basic, least connected tools where you're just uploading a dataset and talking to it, is still really valuable. It's a massive step above what would have been possible two or three years ago, or even a year ago, in terms of understanding the information that powers your business.
Think of the AI not as an oracle that can tell you how to run your business, but as a really good data analyst that's there to answer specific questions you might have about the data you have. It's there to push you in the right direction. If you have a big dataset of reservations, it's really good at answering some of those intuitive questions you might have around your calendar and testing assumptions so that you can make smarter decisions.
The fact is, everyone has about a $130,000-a-year employee sitting in their back pocket if you have ChatGPT on your phone. Even if you're paying 20 bucks a month, that's $240 a year for an employee that would have previously cost $130,000 and probably been out of reach for most businesses. Unless you have 100 million in venture financing, no one has that person on their staff. Use that employee to ask the questions you want to know about your business.
A lot of operators want the results of marketing. They want the results of direct booking campaigns, but they don't have the time to not only implement it, but continue it. Marketing happens over time. It's not an instant thing. Just like building a home, you can't stand it up in a day. It takes time, sequence, interaction, materials, and logistics.
If you're a resource-constrained operator, a one-person team, or your staff is overloaded, the only real step you need to take if you want to do marketing is to get access to your data. Export as much as you can from your property management system, or connect your property management system to a marketing tool that can do marketing with the data that's currently locked away.
Five years ago, marketing software was all about setting up a lot of infrastructure so that you as a marketer could go in and do a whole bunch of things in a very active process. Setting up a platform like HubSpot meant spending quite a few hours on setup and then half a dozen hours a day working on campaigns, building collateral, landing pages, and all sorts of stuff.
That's changed now quite a bit. If you're a time-constrained STR operator and you have the ability to integrate or export your data to a marketing system, choose a system that does it all for you. Either work with marketing agencies that will set up campaigns, build the collateral, the email templates, the lists, the segments, and all of the intelligence that goes into delivering really smart marketing. Or use a system that's built from the ground up to do that in a very low-touch way.
The only reliance for you as an operator is to get the data out of your property management system so that these low-touch systems can create campaigns, run marketing, and reach out to guests on your behalf in a very automated, very low-touch way.
When you're looking at marketing tools or any agency you're planning on hiring, ask how they're using intelligence to take your existing data, your existing customer set, and craft effective campaigns that get you results. But don't just rely on the data you have. Find systems that can collect more data for you.
Every interaction, every website visit, every tiny touchpoint in a guest journey should be logged. This creates a very comprehensive and very opinionated map around what the optimal guest journey looks like. Then you can intelligently find the right person to get the right message and the right offer at the right time.
If you're using an agency or third-party marketing software, be very diligent and make sure that the folks you're hiring approach marketing in an intelligent way. Not just one email campaign a month or voicemail dropping every single person on your list every two months. That's not smart. That's just blasting everybody and hoping something happens.
The questions you should be asking as you're interviewing marketing providers and solutions are: What do they do beyond the bare minimum? What do they do beyond the spray-and-pray, machine-gun-style approach to marketing? If you've got vacancy at a subset of your properties, can they build a list of everyone who stayed at those properties in similar seasons over the past three years so that you're only targeting people who are really likely to rebook at those properties?
Being able to validate whether companies or providers are doing marketing in a smart way will help immeasurably in finding somebody that can actually deliver results in a way that isn't very involved and doesn't require you to spend six hours a day pouring through analytics and reports.
Even the most basic campaign is better than nothing. A lot of people are worried about bugging their past guests. Your past guests want to be bugged. Some of them won't. Some will say, "How dare you message me?" But others will say, "Oh my god, thank you for taking the burden of figuring out where I'm going to go next off my plate because you were awesome."
That very simple act of reaching out, even if you think you're being annoying, is going to get you bookings. It might not happen immediately, but over the course of 12 months, you will increase awareness and recall and name recognition by orders of magnitude simply by being in people's inboxes, by sending them an SMS, by reaching out and saying, "Hey, I like you. Come back and stay."
This is frankly one of the very rare industries where brands are hesitant to do marketing. But every industry in the world does marketing. Every business, every enterprise, every bakery, every cake shop, every hotel, every window pane manufacturer. Spreading awareness and getting the word out there is the foundation of brand building and business building.
Even if you partner with somebody that does the bare minimum, like just sending broadcast campaigns, that's still the zero-to-one step from not doing any outreach to doing broadcast outreach. That's a canyon of difference. Previously, maybe 1% of people remember you voluntarily. If you can increase that to 20% of people remembering you because of an email, that's huge. That's an order-of-magnitude increase in the amount of awareness you get. And over time, that awareness turns into interest, and that interest turns into bookings.
After sending hundreds of thousands of messages on behalf of operators, here are the most important recommendations:
Include your brand name in the from name for the email. Even if someone's coming through and just clearing out their inbox, they're still going to look at the from name. If they're not looking for a trip, they're still going to lodge your name in their mind. Same thing with an SMS. Don't just say, "Hey, come book for the spring." Say, "Hey, it's Steve from Carolina Sand Lodge. We loved hosting you. Come book for the spring." Even if they move on, they see your brand name. And down the road, that's going to have an impact.
Put your personal name in there too. That's the personal connection. There are a million Petars and a million Steves in the world, but there are very few Carolina Sand Lodges. Folks will remember that when you put it in the subject or the first line. But you should also put your name in because that's the relationship. That's what matters in hospitality. It's the experience, the relationship. If they don't care about a relationship, they'll just go stay at a hotel somewhere.
If you have a direct booking website and an about page, put a team photo in there. People really like to know who they're interacting with. Sometimes putting a photo of your management team in the emails humanizes the experience a little bit.
Sometimes people want to try marketing for a month, send out a campaign, blast everyone whose phone number they have with an SMS, and if they don't get a booking, they're done. That's understandable, but it's not how marketing works.
The people you're reaching out to may not be considering a trip right now. Everyone has their booking window. Everyone has when that's a possibility. A trip is a bigger thing than buying a coffee cup for a couple of disposable bucks. It's a high-ticket item. So maybe you're going to get results on that first SMS send, that first email send, and maybe you won't. But that doesn't mean it doesn't work or that it's broken.
Outbound marketing, especially for high-ticket items like this, is a multi-month process of building the pyramid with awareness at the bottom and bookings at the top. There are a couple of levels between awareness and bookings. If you're starting to embark on a journey of outbound marketing, you have to be aware that results are not going to be instantaneous.
It takes time for knowledge to build, for awareness to build, to hone in on the right messaging. That's a completely normal part of the process. If you could just turn on a button that says marketing and immediately start seeing money come in, every business in the world would be overjoyed by that new reality. But that's just not the reality.
Marketing is just building a relationship between your brand and the person you're selling to and the person you want to come back. It takes continuous communication. It takes multiple touchpoints. It takes emails and SMSs and offers and loyalty and rewards. It is not going to be instantaneous.
If you decide to embark on a marketing journey and use intelligent outbound as a way to drive direct bookings, be 100% confident in the fact that you are going to get a ton of direct bookings. But also know that it is going to take weeks, if not months, for the flywheel to really start moving at its desired speed. It takes time for people to warm up. If someone's spending $2,000 and they need to buy plane tickets, they're not going to do that within five days of getting an offer. It might take a couple of conversations with their friends or their spouse or their partner before they decide to make that booking.
Stick with the process. Don't give up if you don't see your first booking within a couple of days, because it's probably not going to happen. But within a couple of months, you're going to be seeing a ton of them.
It's like anything in life that's worth it. You're not going to get in shape from a single month of exercising. You're not going to have a great relationship from a single month of conversations and dates and connection. It takes time. It's a building process. But it's a fun process. You start going from a thousand emails out and one person saying yes, to a thousand emails out and 20 people saying yes, to a thousand emails out and 100 people saying yes. It just builds and builds and builds.
Nobody knows what they're doing right now. We're all learning. We all need each other to learn and to grow and to figure out what's most effective. How do you move forward in this world where intelligence is basically free? It is such an exciting time to be in business.