10 Big Oops We’ve Made Buying Short-Term Rentals (That You’ll Want to Avoid)
Learn from our scars so you don’t have to earn your own the hard way.
You found your Super Property candidate. Your pro forma numbers look great. You’re ready to hit a home run… and then reality hits.
Let’s be real—no matter how many podcasts you binge or spreadsheets you obsess over, the short-term rental (STR) world has a funny way of humbling you. Big things, small things, the unexpected—every investor trips up. Every. Single. Time.
After years of acquiring and managing vacation rentals, we’ve learned that what looks like a dream investment on Redfin can quickly turn into a “what have we done?” moment.
Here are the top mistakes we’ve personally made (yes, all true stories), and how you can avoid repeating them:
1. Not asking enough questions
If something feels unclear—zoning, permits, neighborhood quirks, the vacant lot next door, well depth and flow rate, or septic capacity—keep asking until you have documentation. We’ve made too many assumptions that turned into costly surprises.
👉 Lesson learned: When your gut says, “Hmm, I should double-check that,” listen. When in doubt, ask questions. When you get the answers—trust, but verify.
2. Buying in a vacation market—but in a 100% residential neighborhood with no other STRs
Ah yes, the joy of realizing you’re the only Airbnb on a street full of primary residents. And to make it worse, most of your neighbors are tucked in by 8 p.m. While they may not be STR haters, it’s hard for them to love your guests’ laughter and karaoke drifting through their quiet evening. Cue the “noise complaint” emails because someone dared to… stay up toasting s’mores under the starry sky.
👉 Lesson learned: Make sure you’re actually in a vacation rental–friendly zone, not the bingo district.
3. Not realizing outdoor space is everything
We once bought a gorgeous vacation home… with a “patio” barely big enough for a small table and Weber grill, and a backyard too cramped for a firepit with seating for 8. Guests don’t care about your designer backsplash if they can’t enjoy a cookout or dinner under the stars. Front yard, backyard, and even parking space all matter for STR success—not just the interior.
👉 Lesson learned: In leisure markets, outdoor space sells bookings. Think fire pits, hot tubs, saunas, loungers—somewhere people can live their best Instagram moments.
4. Playing down the power of views
If your photos don’t make someone stop mid-scroll, your listing might as well be invisible. We once passed on a slightly pricier home with breathtaking views (a.k.a "the money shots")—and regretted it when our “budget pick” disappeared into the online noise.
👉 Lesson learned: You can’t Photoshop a view. Pay for it upfront—it’ll pay you back in bookings.
5. Not researching the local talent pool first
A beautiful STR means nothing if you can’t find a reliable cleaner or handyman. We learned the hard way when our “cleaner” disappeared mid-season, leaving us scrubbing toilets in 90-degree heat.
👉 Lesson learned: Before buying, ensure there’s a solid network of STR-friendly cleaners, general contractors, electricians, handymen, and other maintenance pros.
6. Not talking to experienced hosts in the area
Networking is king in the STR world. Casual coffee chats or quick phone calls with local hosts are pure gold. They’ll tell you the real story about seasonality, guest expectations, and local quirks—the kind of insight you won’t get from your realtor and ChatGPT.
👉 Lesson learned: Pick the brains of hosts who’ve been around the block. Their local know-how and free advice can save you thousands in rookie mistakes.
7. Not touring the home, neighborhood, and area before the contingency period expires
We thought we were improving—no more buying sight unseen—but we still didn’t spend enough time touring the home, the neighborhood, and the surrounding area. The result? A chain of surprises we could have avoided.
Now, we start with a scouting tour, attend the home inspection, and do a final walkthrough before closing. If we don’t love the area—including nearby attractions and restaurants—we walk away. Buy what you love!
👉 Lesson learned: Stay at a 5-star STR during your visit. Walk the neighborhood. Listen (literally) to what your guests will hear.
8. Not having a vision for the guest experience before buying
We once bought a house because it “felt right,” but didn’t stop to ask: who’s our ideal guest? Families? Couples? Bachelorettes? These decisions shouldn’t wait until after closing—they drive every design and amenity choice.
9. Under-estimating the tree situation
Debris in your sparkling pool, branches over your new pickleball court, and trees blocking your million-dollar view—it all adds up fast. Those “shade trees” sound lovely until your insurer demands a $5,000 trimming, or you find one leaning a little too close to the roof. Oh, and removal? Try $7–10K per tree.
👉 Lesson learned: Big trees in the wrong spots = big bills and bigger headaches. Budget accordingly—and check those roots before you buy.
10. Ignoring the age of major systems
Roof? Old. HVAC? Original. Water heater? Still running on hope. A failing HVAC or hot water system can tank your 5-star reviews. Replacing these after closing can wipe out your cash flow faster than a guest’s “accidental” red wine spill on the couch.
👉 Lesson learned: Ask for ages, warranties, and service history on all major systems before making an offer.
Make New Mistakes (Not Ours)
Every investor trips up—it’s part of the journey. The trick is to learn, adapt, and share what you’ve learned so others can skip the pain.
💬 What about you? What’s been your biggest “learning moment” or oops in buying an STR?
At Savvy Breezy STR Consulting, we’ve turned our blunders into blueprints for smarter investing. Whether you’re buying your first short-term rental or expanding your portfolio, I can help you:
✅ Evaluate investment opportunities with confidence
✅ Elevate your existing rental’s performance
✅ Stress-test your numbers and due diligence checklist
✅ Design a five-star guest experience that drives revenue
✅ Build an efficient STR operation system (with a reliable local team)
Ready to skip the rookie pain and fast-forward to the fun part—5-star reviews and dependable cash flow?
👉 Book a free discovery call with Savvy Breezy STR Consulting today!