A Simple Checklist for Buying a Vacation Home

Use this simple checklist for buying a vacation home to evaluate location, budget, rental potential, maintenance costs, and long term investment value.

Ever found yourself scrolling past pictures of misty mountain views, winding roads, and cozy cabin decks thinking, “I could live here”? Maybe not forever—but long enough to call it your second home. Places like Gatlinburg, Tennessee don’t just stay on the screen. They pull people in with a promise of quiet mornings, tourist dollars, and fresh air. In this blog, we will share a practical checklist for buying a vacation home that blends everyday decision-making with bigger-picture thinking.

Start With the “Why” Behind the Buy

Before picking out throw pillows or measuring for a hot tub, it helps to understand what kind of buyer you are. A vacation home can mean different things: a quiet family escape, a long-term investment, a short-term rental, or all three if you’re ambitious and not easily rattled. But each goal shifts what matters—whether it’s walkability, resale value, or seasonal demand.

Zoom out a bit, and you’ll notice that the vacation home market is no longer a quiet niche. It’s part of a larger shift in how people think about housing. As remote work moves from trend to lifestyle, second homes aren’t just “getaways” anymore. They’re Plan Bs, income generators, even backup primary residences for the work-from-anywhere crowd.

Markets like Gatlinburg have seen this shift play out in real time. With its year-round demand, strong tourism economy, and relatively affordable entry points, it’s become a magnet for the kind of investor who’s playing the long game. Real estate firms in the area have responded in kind. Local Realty Group, for instance, launched in 2020 with a clear goal: build a team that helps regular people—not hedge funds—turn properties into long-term assets. You’ll see their signs around town. You’ll also see lots of listings for Gatlinburg Tennessee cabins for sale, and chances are, those cabins are moving fast.

Don’t Skip the Math (Even if You’re More of a “Vibes” Person)

Buying a vacation home isn’t just about the view. It’s about whether you can afford to keep looking at that view after the novelty wears off. Start with hard numbers. Think beyond just purchase price—mortgage rates are only one line in a much bigger spreadsheet. Property taxes, insurance, utilities, HOA dues (if any), maintenance, and repairs all need to be part of the upfront math.

Then there’s the question of rental potential. Are you planning to list the property on Airbnb or VRBO when you're not using it? If so, how many nights per year will you need to rent it out to break even? Local short-term rental laws can complicate things fast, especially in tourist-heavy towns where new regulations can pass overnight. You don’t want to find out six months in that the city just capped STR permits.

You also need to be realistic about vacancy. Even in a popular area, you’re going to have down seasons, slow months, and cancellations. Do the numbers still work then? If not, you may be stretching further than you think.

Know What’s Around—And What’s Coming

Location still matters. That old cliché about “real estate being local” keeps getting repeated for a reason. You want to be close enough to points of interest that renters (or your own family) won’t complain about being stuck in the middle of nowhere. But not so close that you’re competing with hotels, chain restaurants, or spring break chaos.

Beyond what’s already built, you’ll want to pay attention to what’s coming. Is there new infrastructure being planned nearby? Are new neighborhoods popping up? Is the city investing in tourism or cracking down on it? A good local agent will know which projects are breaking ground and which ones are just wishful thinking.

For example, in a place like Gatlinburg, being tucked away in the woods may sound appealing—until you realize that getting groceries means a 45-minute drive with no cell service. Balance seclusion with convenience. Also, look for places where public investment is going up. If the city is spending money in an area, chances are value will follow.

Don’t Overlook Management (Even If You’re a Control Freak)

Unless you live next door to your vacation home, you’re going to need help. Managing guests, cleaning between stays, handling maintenance calls at 11 p.m.—it’s a job. You either take it on, or you hire a property manager and give them a cut (usually 10–30%).

Don’t cheap out here. A good property manager keeps your house rented, keeps your guests happy, and saves you from the slow bleed of bad reviews. A bad one racks up costs and lets problems fester until they’re expensive.

Even if you plan to manage the place yourself using apps and smart locks, remember you’re still on the hook when something breaks. Have local contacts—plumbers, electricians, handymen—who pick up when you call. And pay them well. You want your number to be one they respond to, not one they ignore.

Think About the Exit Before You Buy

Not everything goes according to plan. You may decide the hassle isn’t worth it. The market could shift. Your financial situation might change. So before you close, ask yourself: how hard would it be to sell this place in a pinch?

Homes in well-trafficked areas tend to resell faster, but that doesn’t mean you can ignore liquidity risk. Properties with unique quirks—a strange layout, tough access roads, limited financing options—may look charming but turn into dead weight when it's time to exit.

You should also check if there are any deed restrictions or HOA clauses that limit resale or rental use. Some areas are starting to impose strict transfer fees or restrictions that kick in at the point of sale. The fine print matters more than most people think.

Buying a vacation home is the kind of decision that feels personal but is quietly shaped by much larger forces. Rising interest rates, remote work, shifting travel habits, and local politics all play their part. But what really matters, in the end, is your ability to navigate the gap between lifestyle fantasy and financial reality. That doesn’t mean playing it safe. It means walking into the deal with your eyes open, your numbers checked, and your expectations aligned with the facts on the ground.

If you get that part right, you’re not just buying a vacation home. You’re buying options.