Stop Chasing the “Best” STR Markets—Build a Buy Box Instead

Every week, STR (short-term rental) hosts ask the same question:

“What are the best STR markets right now?”

Honestly, I think that’s the wrong question.

Because chasing “hot” STR markets is often how investors end up overpaying, entering saturated markets, and building operations they don’t actually enjoy running.

There is no universally “best” STR market. There are only markets that fit, or don’t fit, your specific goals, experience level, risk tolerance, and lifestyle.

Why Chasing “Best Markets” Is a Trap

The internet is full of gurus and data services publishing “Top 10 STR Markets” lists, and you can easily find the "Top Markets" by beach, mountain, lake, ski towns, urban area, and more.

I followed those lists early on too. I’d see a market being promoted, get excited, do my own research, and sometimes buy there.

But I've learned my lessons. Today, my approach is completely different.

I still pay attention to influencer market picks and STR data reports, but mostly for idea generation, not direction.

Once a market becomes heavily promoted online, competition usually follows fast.

When everyone zigs, it’s often smarter to zag.

The truth is, there aren’t inherently “good” or “bad” STR markets. But some are far more competitive and operationally challenging than others. Unless you’re already a very experienced STR investor and operator, it’s usually smarter to avoid the ultra-competitive markets in the beginning. Orlando, for example, is commonly known as one of those.

And markets can shift incredibly fast.

What felt easy and underserved last year can become saturated this year, especially in smaller STR markets.

Case in Point: Sunday River, Maine

When we entered the Sunday River market several years ago, it felt relatively easy and underserved.

Then it started appearing on “Top 10 STR Market” lists everywhere. Supply surged. Competition intensified. Higher-level operators entered the market.

In smaller STR markets, inventory can grow much faster than demand. What was once “easy breezy” became significantly more competitive.

That’s the risk of chasing hype.

Shift Your Framework: Build a Buy Box Instead

Instead of chasing markets, I now focus on building a Buy Box.

A Buy Box acts like an investment filter. It helps you quickly eliminate markets and properties that don’t align with your goals, operations, or lifestyle.

Instead of asking: “What’s the best STR market?”

Ask:“What markets and properties fit my Buy Box?”

Your Buy Box should be built around four core criteria:

• Regulation – How STR-friendly is the area?
• Competition – How saturated is the market?
• Ease of Operation – Can you build and manage a reliable local team?
• Financial Goals – Does the deal align with your cash flow, ROI, and budget targets?

Getting clear on your financial goals and budget first is critical. Everything else flows from there.

Strategic Filters to Build Your Buy Box

Once you establish your core criteria, layer in additional strategic filters.

1. Personal Use + Vacation Home

Is this purely an investment property, or do you want to use it with your family too?

If personal use matters, only consider markets your family would genuinely enjoy visiting. Proximity to your personal home may matter as well.

Let’s be real: STR ownership is not always glamorous. There will absolutely be days when you ask yourself: “What was I thinking?”

When those moments come, it’s much easier to push through operational headaches if you genuinely love the property and the market you bought into.

2. Diversification Strategy

If you already own one or more STRs, diversification can reduce risk.

Different markets create:

• different seasonality
• different guest profiles
• different cash flow patterns
• different climate exposures

One market slowing down doesn’t necessarily mean your entire portfolio slows down.

3. Cluster Strategy

Sometimes the smartest move is buying another property in the same market.

A second or third property often benefits from:

• existing local teams
• operational familiarity
• established vendor relationships
• reusable systems and guidebooks

There’s real operational efficiency in clustering, but you'd want to be strategic when buying more properties in the same market.

4. Expertise Strategy

Lean into what you already know.

If you’ve mastered operating beach properties, expanding into another strong beach market may make far more sense than jumping into a completely different asset type.

The same goes for ski, mountain, lake, or urban STRs.

Experience compounds.

5. Lifestyle Fit

Be honest about what you actually enjoy operating.

If the idea of snow removal, winter storms, well water, septic systems and remote mountain logistics already stresses you out...

Cross ski and remote mountain markets off your list.

For newer investors especially, this is one of the best places to start:

Identify the kinds of homes you’d love operating, and the ones you absolutely wouldn’t.

The more filters you apply, the shorter and more focused your list of viable markets becomes.

Then something interesting happens:

You stop hunting for markets…and start hunting for great deals that fit your Buy Box.

Stick to Your Buy Box

This is harder than it sounds.

Shiny new listings pop into your inbox every day. Some will absolutely tempt you. (I'm tempted almost one a week!)

Whenever I feel that pull, I remind myself to run every opportunity through my Buy Box first.

No matter how beautiful the property looks.

No matter how exciting the pro forma sounds.

If it doesn’t fit the Buy Box, I pass.

Because you’re not looking for the “best” market.

You’re looking for the best deal that fits your Buy Box.

That’s how you build an STR portfolio that’s not only profitable, but sustainable and enjoyable for the long haul.

Need help building your Buy Box, evaluating a market, or validating a deal?

Or maybe you already purchased an STR and want help launching it strategically and stress-free?

That’s exactly what we do at Savvy Breezy STR Consulting — helping hosts solve operational challenges, refine systems, and build STR businesses that are both profitable and sustainable.

Book a call today and let’s figure out the smartest next step for your STR goals.