Your Guide to Short-Term Rentals—Physician Entrepreneur Edition

If you're like most physicians I coach and support, you're not necessarily looking to quit medicine altogether—but you are absolutely looking for options.

You want a lifestyle with more autonomy, more income flexibility, and greater control over your future. You want to build wealth, reduce burnout, and reclaim your time. And if you’ve paid off your student loans or are on your way to paying them off, short-term rentals (STRs) could become the fastest off-ramp to your version of professional freedom.

The short-term rental model isn’t just a side hustle—it’s a business strategy. One that, when executed properly, can generate outsized returns compared to traditional real estate, offer unique tax advantages, and provide a stepping stone to a more entrepreneurial lifestyle.

In this post, I’ll break it down for you from a physician’s point of view, using real-life experiences—including my own—and layer in practical tools and resources from the Physician Entrepreneur Academy (PEA) at SimpliMD.

What Is a Short-Term Rental (STR)?

Short-term rentals are furnished residential properties—like condos, homes, or cabins—that are rented for periods less than 30 days, often through platforms like Airbnb or VRBO. While long-term rentals feel more like passive income over time, short-term rentals require a more hands-on, business-minded approach. You're not just renting a home; you’re operating a boutique hotel.

That nuance is crucial, especially for physician entrepreneurs who need to account for time, effort, and risk in addition to ROI.

Why STRs Offer a Fast Track for Physician Entrepreneurs

Short-term rentals shine because they generate significantly more income per occupied night than long-term leases. A $2,000/month long-term rental might bring in $24,000 per year. But that same property as an STR could generate $300 per night for 15 nights a month—$54,000 annually. Even factoring in cleaning fees, platform commissions, and higher vacancy rates, the margins can still double or triple that of a long-term rental.

But don’t just take my word for it—let’s look at a physician case study.

Case Study: Dr. Lewis’ STR Leap from Locums to Lifestyle

Dr. Lewis, a PEA-SimpliMD member and emergency medicine physician in Michigan, began exploring STRs during the pandemic when locums work dried up. He and his spouse found a small lakefront cottage in SouthWest Michigan, and after learning about bonus depreciation through our PEA-SimpliMD blog, they took the leap.

Initial Investment:

• $450,000 purchase price

• $90,000 down payment

• $35,000 for renovations and furnishings

First Year Results:

• $72,000 gross revenue

• $25,000 net cash flow

• $110,000 bonus depreciation offsetting clinical income

They now own three properties, including a ski rental in Colorado, and Dr. Lewis works half the clinical hours he used to.

The (Often Overlooked) Costs of STRs

While STRs can be lucrative, they come with higher operational demands:

• Cleaning Costs: Frequent turnovers mean constant cleaning and restocking.

• Furnishings & Amenities: Guests expect quality and convenience.

• Marketing & Platform Fees: Professional listings are a must.

• Seasonality & Vacancies: Occupancy fluctuates with seasons.

• Management Costs: Outsourced management often costs 20–35% of gross revenue.

Risk Factors Physicians Must Consider

1. Legislative Risk

Zoning rules and licensing crackdowns are increasing. Stay informed and engaged with your local community and networks like PEA-SimpliMD. I have been involved in a big zoning and regulatory battle involving STR’s in South Haven, Michigan. STR owners had to unite and higher an attorney to fight the local city leaders. Thankfully it appears we have won.

2. Market Saturation

Use tools like AirDNA and PriceLabs to evaluate local demand and pricing.

3. Life Curveballs

Have a backup plan if travel shuts down or bookings dry up. Can your property cash flow as a long-term rental?

The STR Tax Advantage: A Physician's Secret Weapon

Here’s where it gets exciting:

• To claim long-term rental tax losses it usually requires Real Estate Professional Status (REPS) which requires 750 hours of material participation. This is hard to achieve for a doctor!

• STRs, however, have a loophole: With 100+ hours of material participation, plus you can take bonus depreciation to offset W-2 or 1099 income—without REPS.

This is a massive advantage, especially if your spouse can help handle the rentals.

Learn more through our partner the Semi-Retired MD where they unpack The Short-Term Rental Tax Loophole. This loophole pertains to owning short-term rentals, which have an average length of stay over the calendar year of seven days or less. When you buy a STR, you can meet material participation hours for the year between you and your spouse. Here are a couple of articles diving into the details of how to access the tax savings of STRs.

Can This Replace Your Clinical Income?

Let’s say you have $500,000 to deploy:

• $100K down on 5 STRs ($500K each)

• $100K for furnishings

• 20% net return = $100K/year cash flow

• Add appreciation, tax savings = $150K+ annual value

With scale and strategy, you can shift to professional management and gain true autonomy.

This was my approach with my STR Simpli SoHa in South Haven, Michigan.

Ready to Dive Deeper?

Download my free guide: Your Guide to Short-Term Rentals: Physician Entrepreneur Edition

I highly recommend the thorough STR evergreen course from the Semi-Retired MD’s called Accelerating Wealth Course. It will provide you with every tool you need to hit a home run with your first STR.

Take the Next Step with PEA

The system won’t save you—but entrepreneurship might.

Join the Physician Entrepreneur Academy to access multiple small business resources that help you with scaling real estate portfolios.

Membership Options:

• PEA Explorer ($99/year): Foundational tools, community, STR starter kit. Join here

• PEA Builder ($499/year): Pro formas, legal templates, tax tools. Join here

• PEA Pro ($999/year): Full access to coaching, workshops, and premium tools. Join here

Final Thoughts: Entrepreneurship Is the New Wellness

This isn’t about quitting medicine.

It’s about buying back your time.

If you're ready to think differently, act strategically, and build a life you own, STRs may be your best next move.

Let’s do this together.

Related SimpliMD E-books & Posts

• The Physician's Guide to Cost Segregation: Maximizing Your Real Estate Investments

• Physician's Vacation Home Investment Checklist

• Say Yes To Self-Employment

Throwback Wisdom:

"Once you realize you are a business, you’ll never look at a job the same way again."

Read more wisdom at The Independent Doctor Blog

Identity Shift Step

Still thinking like an employee? It’s time to own your time, your work, and your income.

👉 Start Your Transition with PEA Explorer Membership or download my free e-book "The Entrepreneurial Physician’s ESCAPE from Corporate Medicine"

Let’s build something that sets you free.