Choosing the right realtor can make or break your STR investment—no matter your experience level. Over the years, we’ve managed a dozen real estate transactions across multiple states—buying, selling, and everything in between. Every deal comes with unique opportunities and hidden risks, and we’ve made some big mistakes along the way—lessons we’ll never repeat and hope no new STR investor ever has to experience.

Realtors also vary widely. Some are absolute gems—I’ve learned so much from them and still stay in touch years later. Others… not so much. That’s why it’s crucial to know how to vet a realtor who truly understands STR investing, not just traditional residential sales. This guide walks you through exactly how to do that so you can avoid costly missteps and make smarter investment decisions.

1. Make Sure They Understand STR Investing (Not Just “Vacation Homes”)

Many realtors specialize in primary residences or second homes. STR investing is a different world, and you need someone who thinks like an operator—not a vacation-home enthusiast.

Questions to ask:

• “How many STR investors have you worked with in the past year?”
• “What STR-specific properties have you helped clients buy recently?”
• “Do you personally own or operate an STR?”
• “Do you co-host or manage STRs for clients?”

Red flag: They focus on “cute cabins,” “nice views,” and “great for families,” and never mention metrics like ADR, occupancy, COC, ROI, or net revenue.

2. Vet Their Knowledge of Local STR Regulations

Regulations can make or break an STR deal. If your agent can’t speak confidently about local rules, they’re not equipped to guide you.

Questions to ask:

• “What are the STR rules in this town or county?”
• “Which zones allow STRs by right? Which require permits?”
• “Where do you check for updates?”

Red flag: “Oh, it’s fine. Trust me—everyone Airbnbs here.”

3. Confirm They Understand STR Numbers and Revenue Drivers

Accurate projections are essential for evaluating an STR investment. Your realtor should know how to analyze—and sanity-check—the data.

Questions to ask:

• “What tools do you use to estimate STR performance?”
• “What’s the realistic ADR and occupancy range for this type of property?”
• “Which amenities are essential for competitiveness in this market?”

Red flag: They quote the highest Airbnb comp without adjustments or use long-term rental numbers.

4. Assess the Realtor’s Due Diligence Support

STR deals require deeper due diligence than primary homes. You need an agent who helps uncover (not hide) potential issues.

Questions to ask:

• “Do you help verify utilities, septic capacity, well output, internet speed, or HOA/POA rules?”
• “Can you arrange inspections and contractor walk-throughs?”
• “What optional inspections do you recommend for this area?”

Red flag: They rush you to submit an offer without checking important STR-specific details.

5. Evaluate Their Market Knowledge Beyond the MLS

A strong STR realtor knows the guest demand cycle, not just the MLS feed.

Questions to ask:

• “When is peak season, shoulder season, and slow season?”
• “Which neighborhoods consistently perform best for STRs—and why?”
• “What amenities do guests expect in this market?”

Red flag: They can’t explain STR-specific demand patterns.

6. Understand Their Negotiation Style for Investors

Investor negotiations are different from emotional homebuyers. You need an agent who knows how to structure an investment-minded deal.

Questions to ask:

• “How do you negotiate for STR buyers?”
• “What seller credits or concessions have you secured recently?”
• “What inspection findings matter most for STRs?”

Red flag: Treating your purchase like a sentimental vacation-home buy.

7. Ask About Their STR-Friendly Vendor Network

A great STR realtor has a deep bench of local vendors who understand vacation rentals and quick turnovers.

Questions to ask:

• “Do you have STR-friendly cleaners, handymen, HVAC techs, contractors, or hot tub services?”
• “Who do you recommend for STR insurance, staging, design, and photography?”

Red flag: Only having traditional residential vendors—or none at all.

8. Evaluate Communication and Availability

Buying an STR—especially out of state—requires speed, clarity, and responsiveness.

Questions to ask:

• “What’s your typical response time?”
• “Do you provide video tours for remote buyers?”
• “How do you keep clients updated during escrow?”
• “Is there any post-closing support you offer?”

Red flag: Vague answers, slow or inconsistent communication and pushy tactics.

Bonus Question: Test Their Real STR Knowledge

Ask this one powerful scenario question:

“If a property is a revenue dud in this market, how would you know?”

A high-quality STR realtor will mention:

• regulations
• location factors
• layout limitations
• guest appeal
• amenity gaps
• seasonality
• accurate comps

A poor-quality realtor will just say:

• “It should do fine.”
• “It's a great deal.”
• “Airbnb is booming here.”

Final Tip: Hire the Right Realtor for the Right Job

If you want an investment-grade STR, don’t hire someone who thinks like a vacation-home realtor—even if they were recommended by family or friends.

You want someone who thinks like:

• an operator
• an analyst
• a risk manager

Your agent should help you make a smart, scalable investment—not just sell you a pretty property.

👉 Get the Free STR Realtor Vetting Checklist — Delivered Straight to Your Inbox

Feeling more confident about interviewing realtors is great — but having the right questions in your back pocket makes all the difference.

Grab my FREE STR Realtor Vetting Checklist, designed to help new and aspiring short-term rental investors avoid rookie mistakes and confidently choose a realtor who actually understands investment strategy, STR regulations, and revenue potential.

📥  Fill out the form below and get it in your inbox.

Ready for Expert Guidance Before You Buy?

Navigating your first STR purchase doesn’t have to feel overwhelming. If you want personalized support, deal analysis, or coaching to avoid rookie mistakes, Savvy Breezy STR Consulting is here to help.

From identifying the right market to evaluating deals, launching your STR listings and building solid operation systems, we’ll walk with you step-by-step so you can run your STR business confidently and profitably.

👉 Book a free discovery call today and start your STR journey the smart way.