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Hey, Olivia! 👋

Welcome back to another edition of BiggerStays, the all things short-term rental newsletter.

Last year, Scottie Scheffler was arrested outside the PGA Championship. This year? He just won the whole thing. That’s what we call turning a short-term setback into long-term wins: STR hosts, take notes.

– Garrett Brown (BiggerPockets STR Expert)

In this email:

Let’s check in! ⤵️

🗺️ 10 STR Markets Under $500K

Short-term rental investing isn’t about grabbing the cheapest fixer-upper and praying for five-star reviews; it’s about picking high-demand markets with flexible rules, strong guest appeal, and the right mix of revenue-boosting features like hot tubs, pet-friendliness, and great design.

We just broke down the 10 best STR markets under $500K, using the latest May 2025 data. These aren’t low-yield leftovers—they’re carefully ranked by revenue potential, occupancy, and investability. You’ll get detailed stats, zoning info, and amenity strategies for each city.

One surprise? Lancaster, PA. With a median price of just $360K, top listings are pulling in $120K+ a year by leaning into pet-friendly, hot tub-equipped setups that attract weekenders from Philly, D.C., and beyond.

From beach towns to wine country, if you’re looking for your next STR that actually pencils out, this list is your roadmap.

Housing Market Is Changing (Find Deals NOW)

The housing market is entering a new phase: one we haven’t seen in years. Prices are softening, inventory is rising, and buyer power is quietly returning. In this month’s update, Dave Meyer breaks down what this shift means for investors and why this moment could be a buying opportunity in disguise.

From the widening gap between list and sale prices to surprising regional trends (Jacksonville down nearly 4%, while Milwaukee is up 12%), Dave explains how to navigate the changing dynamics without falling for the headlines. He also digs into updated rent and vacancy data, mortgage rate predictions, and how he's personally adjusting his portfolio strategy.

Luckily, if you are ready to find deals NOW, BiggerDeals is live and ready to help you find cash-flowing deals today. If you’re wondering whether to buy, sell, or hold right now, this is the update you can’t afford to miss.

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Want to see the deals? Text REI to 33777 or click below to start building passive income like a pro.

STR Insurance Costs—Solved in Seconds

Not sure how much to budget for short-term rental insurance? We’ve teamed up with Steadily to create a free calculator that gives you a fast, reliable estimate based on your property’s location, type, and value.

Whether buying your first Airbnb or scaling up your portfolio, this tool takes the guesswork out of one of the most overlooked (but crucial) expenses in STR investing.

STR Headlines

Hot Topics from the Short-Term Rental & Airbnb Investing Forum, presented by Hospitable 

STR Insurance too high due to previous owner's insurance claim...advice? This new STR operator is dealing with high insurance quotes because of the previous owners. Find out what other STR hosts have done to deal with these issues and what you can learn from it.

More sizzling discussions:
🔥 How to set up furniture in a new STR?
🔥 Should I be listing somewhere other than Airbnb and VRBO?
🔥 How to get listed on Google Vacation Rentals and Marriott Homes & Villa

Join the conversation and level up your STR knowledge. Your next big strategy could be just a click away!