Short-Term Rentals: 10 Things to Know About Sites Like Airbnb

Short-term rentals for vacation travel have exploded in the age of mobile data. Since its founding in 2008, Airbnb has helped more than 2 billion guests book and stay at short-term rentals in over 220 countries. Whether you plan to stay in one of the cheapest countries around the world or a nearby town, you'll find diverse property types and prices.

But Airbnb’s explosive growth isn’t without its nightmares. The internet is riddled with scary scenarios: Bedbugs, last-minute cancellations, over-the-top host cleaning requests and bare-bones amenities. Worse, poor customer service has left guests scrambling for new digs.

“We booked an Airbnb last year for the Montreal Jazz Festival. After paying our deposit, we had no communication, including basics like where to get the key,’’ says Christi Cassidy, a literary publicist who lives in Hudson, New York. When Christi and her partner, Nan Kinney, called Airbnb support for help, they were told their Montreal rental was a fake listing. Surprise!

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“They refunded our money and offered to help book us another Airbnb, but nothing else was available so we wound up staying in a Marriott Courtyard for twice the price,’’ she says.

As the new year approaches, it’s not too early to start looking for summer rentals in the better vacation areas. Here are some tools and tricks for successfully booking short-term rentals.

1. The top short-term rental sites have different strenths

• Airbnb: By far the largest and best-known short-term rental website, with more than 7 million listings in 100,000 cities worldwide.
• Vrbo: Established in 1995, the site focuses on private homes and tends to attract a more mature clientele looking for the privacy of whole-home rentals.
• Booking.com: With over 6 million listings in over 224 countries, Booking.com offers hotels alongside short-term rentals, making it valuable for comparing apartment, condo or home prices vs. hotels at your choice destination.
• Expedia: Like Booking.com, this online travel agency offers short-term rentals and vacation homes alongside hotel listings.
• TripAdvisor: A wealth of customer reviews helps ensure a satisfying rental.

2. Know your assignment

Searching listings can prove overwhelming. A weekend in Nashville will alone serve up over 1,000 different rental options. That’s why you need a game plan, says Adrian Selby, a retired entertainment and communications executive from Litchfield, Conn.

“Let’s say we are going to London,’’ Selby says, adding: “I scour the listings, create a short list that I review with my wife Maggie, then we pick one. It’s a lot of work to get it right, and even then, you can be fooled by artful photos!”

3. Know your filters

“Make sure the property has what you need, whether it's a coffee machine, blender, pool access or beachfront views. These details can make a big difference in ensuring a comfortable, pleasant stay,” says Caitlin Johnston, co-founder along with Stefanie Medd of Host & Stay, a company that helps short-term rental owners maximize their listings.

If an amenity is extremely critical, New York City attorney Linda G. Marynov advises confirming with your host before you book.

“We rented from Vrbo in Chatham, Mass. It was a big, beautiful six-bedroom house, billed as having a ‘chef’s kitchen.’ Except it wasn’t a chef’s kitchen. The pots, pans and colander were rusty. The oven didn’t work properly. There were two sinks, but one leaked. The barbecue wasn’t operational. We were there to celebrate and cook with friends. It was beyond disappointing,’’ she says.

4. There is good news for consumers

As their reputations got hammered, short-term rental platforms learned and evolved. They’ve even persuaded hosts to stop leaving picayune checklists for pre-departure cleanup.

“One major update is AirCover on Airbnb, which provides 24/7 support, booking guarantees, protection against last-minute cancellations or other issues with the property,’’ says Host & Stay co-founder Stefanie Medd.

To fight against fake listings like the one Christi Cassidy and Nan Kinney booked in Montreal, Airbnb has begun verifying listings to ensure that they’re real, their location is accurate and that the property’s “photos and descriptions align with what you’ll experience during your stay,’’ Caitlin Johnston says.

In June 2024, Airbnb implemented its major disruptive events policy, allowing guests and hosts to cancel without penalty when weather or natural disasters occur. Good thing in the age of Category 5 hurricanes.

5. Booking far in advance vs. last-minute deals

Nerdwallet studied Airbnb prices in 10 top markets and found that booking four weeks out yielded the lowest median price. Trying to hedge having the best rentals available vs. best possible price is definitely a time-consuming game.

Unlike airlines or hotels that compete against each other, Airbnb controls its search tool.

“This means that the platform has no incentive to simplify the process of finding discounts or helping users know when a property offers a good or bad deal on any given date,’’ says travel expert Sam Kellis.

Landing a cool spot in Paris in June or New Year’s Eve in New Orleans requires planning and booking in advance, turning pricing into a secondary consideration. If you want bargains, look for deals and destinations off-peak.

6. Read the reviews carefully

Without reviews, short-term rental platforms would never survive. Pictures may tell 1,000 words, but it’s the published feedback from other guests that’s the basis for determining an Airbnb rental’s quality and reliability.

“It’s important to make reading the reviews a priority — especially if the property has less than a 5-star rating. Look into why past guests may have left lower ratings and if there are any patterns in the feedback,’’ says Andrew Peterson, a real estate agent who manages rental properties in the Fort Lauderdale, Fla., area.

7. Is a short-term rental cost-effective?

Cleaning fees, service fees, extra guest charges and local taxes can leave guests with sticker shock.

For instance, a luxe home in Nashville for a week in February costs $9,366.90 or $1,873.38 per night. Add on the $533 cleaning fee, $1,397.63 in Airbnb service fee, plus $1,750.51 in taxes, and that week totals $13,048.04.

8. Hosts may offer discounts for longer stays

According to Nerdwallet, the nightly rate for a seven-night Airbnb stay is 32% cheaper than the nightly rate for a one-night stay. A 30-day booking averages a 46% discount per night over the cost of one night.

The Selbys say their go-to travel strategy is to use Airbnb only for longer stays — never for less than a week. “Last year in Paris we had a seven-night stay for a total of about $6,000. A nice hotel would have been twice that,’’ Adrian Selby says.

9. Know who your host is and how they communicate

Instant booking is available for many rentals, but before you commit and pay the deposit, reach out to the host. Airbnb and other rental sites have a message function that will deliver your inquiry directly to the host. This will set the stage for what kind of communication and service you can expect during your stay.

And remember: There are no front desks or concierge services. You might need a phone app to gain entry to the place. There could be a lockbox. A key might be in a flower pot. Make sure you have your host’s contact information on hand.

10. Make sure you understand the cancellation policy

“While many guests prefer lenient policies for flexibility, they don’t always review these policies closely before booking. In fact, only a percentage of guests ensure that the cancellation policy aligns with their needs,’’ Stefanie Medd says.

“I also look at the cancellation terms,” says Adrian Selby. “I always reject ones that have a no-cancel policy.’’

Note: This item first appeared in Kiplinger Retirement Report, our popular monthly periodical that covers key concerns of affluent older Americans who are retired or preparing for retirement. Subscribe for retirement advice that’s right on the money.

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