Should You Rent Out Your Property? 3 Big Concerns (and How to Handle Them)

Thinking about turning a property you already own into a short-term rental (STR) on platforms like Airbnb or VRBO? You’re not alone, and you’re also not alone in having a few big concerns before handing over your keys to a stranger. Whether it’s a home you live in part-time, an inherited property, or a dedicated rental, hosting guests can be a rewarding way to earn extra income.

And let’s be honest: there are a few common fears that stop many would-be hosts in their tracks.

Let’s walk through the three most common concerns people have before renting out their property, and how you can prepare, protect, and profit with peace of mind.

Concern #1: What if guests damage my property?

For many new hosts, the biggest fear is simple: “What if someone breaks something… or trashes the place entirely?”

The Reality

Yes, wear-and-tear will happen. From scuffed floors to the occasional broken wine glass, your home will no longer be pristine once it becomes a short-term rental. But true, serious damage is rare, and when it does happen, there are systems in place to protect you. I have been hosting on Airbnb for 9 years (time flies!) and have had probably 4 awful guests in terms of mess left behind.

Common Risks Include:

• Ruined linens or towels
• Furniture stains from food, drinks, or pets
• Broken appliances
• Clogged toilets or drains
• Wall dings from luggage or careless guests
• Theft or missing decor

How to Prepare:

• Use damage-resistant materials: Choose washable, durable fabrics and surfaces in your STR. Darker bedding hides small stains better than crisp white, and hard flooring holds up better than carpet.
• Protect valuables: Don’t leave sentimental or expensive items in the rental. Lock them up—or better yet, remove them.
• Inventory your space: Create a master checklist of what’s in each room, down to dishes and remote controls.
• Use platform protection: Airbnb’s AirCover offers up to $3 million in damage protection. It’s not perfect, but it’s better than nothing.
• Consider extra protection: Many hosts also use short-term rental insurance, which is more robust than homeowner’s insurance. Companies like Proper Insurance and Slice cater specifically to STRs.

Pro Tip:

Some hosts leave a note saying their cleaner reports anything that’s missing or broken. This alone can prevent problems.

Concern #2: What if I get bad guests?

Nobody wants a nightmare guest. And while most travelers are respectful and tidy, hosts still worry about:

Guest Horror Stories:

• Parties that leave behind alcohol bottles and broken furniture
• Guests who sneak in extra people or pets
• Constant demands, complaints, or attempts to get a refund
• Neighbors reporting noise or parking issues

How to Prepare:

• Vet your guests: Platforms like Airbnb let you require ID verification and only accept guests with good reviews. For new guests, review their profiles and message with them before accepting.
• Set clear house rules: Include rules about noise, guests, pets, and check-in/check-out in your listing—and post a printed copy in your home.
• Use smart technology:
  • Install noise monitoring devices (like NoiseAware) to alert you about parties.
  • Use smart locks with unique codes to track entries.
  • Consider a security camera on the exterior (but never inside!).

How to Respond:

If a guest breaks the rules, document it. Take photos and videos. Calmly message them with your concerns. If it escalates, involve Airbnb or VRBO support early.

Pro Tip:

Pre-set your listing to decline same-day bookings or limit booking to guests who’ve completed a certain number of stays. This small filter often weeds out trouble.

Concern #3: What about legal issues, taxes, or getting in trouble with the city?

Short-term rental regulations have exploded in recent years. From permits and zoning rules to neighborhood caps and tax requirements, many hosts are shocked by how much red tape can be involved.

The Risks:

• Getting fined or shut down due to zoning restrictions
• Trouble with your HOA for renting out your unit
• Owing back taxes on STR income
• Being required to collect occupancy taxes on behalf of the city

How to Prepare:

• Research local laws: Google “[your city] short-term rental regulations.” Look for info on permits, business licenses, and zoning restrictions.
• Check for HOA rules: If you’re in a condo or community, your HOA might prohibit STRs or require long-term leases.
• Get permitted: Many cities (like San Diego, Austin, and New York) now require STR registration or certification.
• File your taxes: STR income is taxable. Platforms like Airbnb may send you a 1099 if you earn above a certain amount. You may also owe lodging taxes (also called occupancy or tourist taxes).
• Work with a tax pro: There are tax advantages to STR income (like depreciation), but you’ll want someone who knows the ins and outs of the space.

Pro Tip:

Use tools like Minoan, Lodgify, or HostGPO to manage legal and logistical aspects of hosting. Many offer compliance guides specific to your region.

Final Thoughts

Becoming a short-term rental host isn’t without risks, and every risk can be reduced with the right preparation.

• Concerned about property damage? Choose guest-proof furnishings and document everything.
• Nervous about nightmare guests? Vet carefully, set expectations, and use tech tools.
• Not sure about local laws? Take a few hours to get educated before you launch.

At the end of the day, the opportunity for income, flexibility, and even property appreciation makes short-term rentals an exciting (and smart) strategy for many owners.

Still on the fence?
Head to my other post on the KP_BNB blog, FAQ: Operating a Short-Term Rental (With Real-World Scenarios & Solutions) for more advice, host-tested tips, and step-by-step guides that help everyday owners succeed in short-term rentals, with fewer headaches and more 5-star reviews.

I’m here if you want to chat!

– KP