One of the questions we’re asked most often is:
“Do you think this property would make a good Airbnb?”
It’s a fair question—but it’s also the wrong place to start.
When people begin looking for a short-term rental, they often fall in love with a house before they understand the market. We’ve done it ourselves. You walk into a charming farmhouse or a cozy cabin and immediately start picturing guests gathered around the fire pit or sipping coffee on the deck.
There’s nothing wrong with that.
The problem is that a great house doesn’t always make a great short-term rental.
The best investments happen when you fall in love with a property after you’ve confirmed the numbers, the demand, and the regulations all make sense.
Start With the Destination, Not the Property
Before you browse listings or schedule a showing, spend some time getting to know the market.
Ask yourself:
A lake community attracts different travelers than a ski town, college town, wine region, or beach destination. Families, couples, business travelers, and outdoor enthusiasts all have different priorities.
The more you understand your future guests, the easier it becomes to recognize the right property when you find it.
Study the Competition
One of the best ways to evaluate a market is to look at the properties already succeeding there.
Spend an evening browsing Airbnb and VRBO.
Don’t just glance at the nightly rates. Read the reviews. Look at occupancy calendars. Notice which amenities appear over and over. Pay attention to the photos and how hosts describe their homes.
Ask yourself:
You’re not looking to copy another host.
You’re looking to understand what guests value in that market.
Think Like a Guest
This may be the most important shift you can make.
When you’re evaluating a property, stop thinking like a buyer and start thinking like a traveler.
Imagine you’ve driven four hours to spend a long weekend there.
Would you be excited to arrive?
Is there a beautiful view?
Can guests walk to restaurants, breweries, hiking trails, or the beach?
Does the backyard invite people to linger around a fire pit?
Can families gather comfortably in the living room?
Sometimes it’s not the square footage that makes a property memorable.
It’s the experience.
Look Beyond Cosmetic Updates
Paint colors can change.
Cabinets can be replaced.
Furniture comes and goes.
The things that are hardest—and most expensive—to change are often the things that matter most.
As you’re evaluating a property, pay close attention to:
A property in a fantastic location with outdated finishes often has more potential than a beautifully renovated home in a less desirable area.
Understand the Numbers
Excitement is wonderful.
Cash flow is essential.
Before making an offer, estimate your potential income and compare it to your expenses.
Be realistic.
Consider:
A property needs to work financially—not just emotionally.
Don’t Forget Local Regulations
We’ve seen people purchase beautiful homes only to discover later that short-term rentals were heavily restricted—or not allowed at all.
Before you buy, confirm:
Doing this homework before closing can save you significant time, money, and frustration.
Consider the Guest Experience
Some homes naturally make hosting easier.
As you walk through a property, think about how guests will use the space.
Can several people gather comfortably?
Is there enough parking?
Are the bathrooms convenient?
Is the kitchen functional for families?
Where will guests store luggage?
Is there outdoor space they’ll actually enjoy?
The answers to these questions often matter more than whether the countertops are granite or quartz.
Don’t Chase Every Trend
Every year, a new type of short-term rental seems to dominate social media.
Treehouses.
Shipping containers.
Domes.
Tiny homes.
Unique properties can certainly be successful, but don’t assume something unusual automatically means profitable.
The most successful rental is often the one that best matches what travelers in that market are looking for.
Buy for your market—not for Instagram.
In Our Experience
Our first successful short-term rental was a 1915 farmhouse that had seen better days. It certainly wasn’t the easiest property we could have chosen, but it was in the right location, had plenty of character, and offered the kind of experience guests were looking for. After a complete renovation, it became one of our most rewarding projects and eventually sold with an impressive return on investment.
Since then, we’ve built a home with a dedicated short-term rental wing, transformed an ADU into one of our most profitable rentals, and converted a primary residence into a luxury mountain retreat.
Each property was different.
Each served a different type of guest.
But they all had one thing in common:
We chose the property because it fit the market—not because it was our dream home.
That single mindset has guided every successful investment we’ve made.
Final Thoughts
There isn’t one perfect short-term rental property.
The best property is the one that matches its market, delights its guests, and makes financial sense for your goals.
Do your research.
Trust the numbers.
Think like your future guests.
And don’t be afraid to walk away from a property that doesn’t check the right boxes. Another opportunity will come along.
Finding the right property is one of the most important decisions you’ll make as a host. Take your time, ask plenty of questions, and remember that a successful short-term rental starts long before your first guest checks in.
In Booked Solid, we devote an entire chapter to evaluating properties, researching markets, estimating income, and identifying the features that consistently lead to five-star stays. We hope that you’ll make your first purchase with confidence—and avoid the costly mistakes that many of us make when we’re just getting started.
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