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Vacation rental tips even the experts don’t know

Think you know everything there is to know about finding a vacation rental? Think again, say vacation rental experts.



From when to book to what to look for, you might be missing important details that could dramatically improve your stay.

Here’s one: Most vacation rental bookings happen in January, February, and March, as travelers try to secure the best rates, according to Bank of America’s 2018 spending and transaction data. But a select few renters wait until the last minute to get an even better rate. Last year, the highest single-spending days for vacation rentals were June 5, July 18 and Aug. 1, as bargain hunters scoured the internet for last-minute deals.

That’s what Catherine Olson does when she travels with her family. 

“It takes a bit of courage to wait until the very last minute to book,” says Olson, who works for an airline in Salt Lake City. “The sweet spot is typically two to three days before arrival. Find the vacation rentals that are still available and send the owner a note requesting a discount, since the odds of booking the home by this point are slim. Don’t offer a price. Let the owner come back to you.”

On more than one occasion Olson has gotten up to 50% off by doing that. So have I.

Screen your rentals carefully

That’s the advice of Marjorie Yasueda, a retired travel agent and experienced home renter. If you’re renting on HomeAway or Vrbo, look for the “Premier Partner” designation. On Airbnb, check for the “Superhost” badge. These are properties known for outstanding service.

“Examine the photographs, read the reviews, check the cancellation policy and decide if the property is in a good location, in terms of transportation, shopping and sightseeing,” she says. 

Pack a knife to use in that kitchen

If you’re planning to do your own cooking, do yourself a favor and pack your favorite knife (in checked baggage if you’re flying). Rental properties almost never have sharp knives making food prep a pain.

Even if you think you’ve found the perfect rental, Olson adds one more piece of advice: If you’re planning to do your own cooking, always pack a chef’s knife in a checked bag.

“I have never, ever rented a property with a decent knife,” she says. (Come to think of it, neither have I.)

Ask lots of questions

A vacation rental is not a standard product, which means there’s a lot you don’t know – and shouldn’t assume you know. That’s the advice of Amina Dearmon, owner of Perspectives Travel, a Virtuoso-affiliated travel agency in New Orleans.

“I think the key to having a great rental experience is to ask the owner lots of questions up front,” she says. Make a list now. 

“I’ve asked about the air-conditioning unit, pool depth, pest control and heating source for the stove, among other things,” she adds.

Professional vacation rental owners won’t push back when you ask these questions, because they know that no two vacation rentals are identical. And they also sincerely believe that the best customer is an informed customer.

Start a dialogue

Don’t wait until the night before you arrive to introduce yourself. After you book your rental, say hello.

“Your first message should be a few sentences long that describes your group, the purpose of your visit, and most importantly, conveys enthusiasm,” says  Andreas King-Geovanis, a managing partner for Sextant Stays, a vacation rental company. “Hosts love to delight their guests and will go above and beyond – think early check-in, late check-out, or a complimentary bottle of wine – for guests who reciprocate positive energy.”

I’m a frequent vacation rental guest. In fact, I practically live in rentals. Many of these insider tips are not obvious, and it took a while to understand the importance of screening a rental or conversing with a host. And it took me almost a decade to figure out the late-booking trick.

Learn from my mistakes, please.

More expert vacation rental tips

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If the host seems prompt and polite, you can expect to be well taken care of. (Source)

Prompt replies matter

If you contact an owner and it takes days to hear back, that may be a sign of trouble. “See how long a reply takes,” says Ty Newcomb, a professional photographer, and frequent vacation rental guest. “Usually, if the host seems prompt and polite, you can expect to be well taken care of.” And if not? Maybe look elsewhere for a rental.

Do your hosts go the extra mile?

The best hosts offer concierge services at no additional cost, which help you book tours and make restaurant reservations. “Anything our guests need, so they have a stress-free vacation,” says Jorge Morera, who owns a vacation rental in Costa Rica.

Also, if your hosts greet you in person when you arrive – or at least speak to you by phone before you arrive – it’s a sign you have a great rental.

Pay attention to Google Street View

Many vacation rental guests consult Google Maps to find a rental’s proximity to mass transit or attractions. But Tamara Gruber, a frequent vacation rental guest and family travel blogger, also consults Google Street View. 

“It will give you a better sense of what the neighborhood looks like,” she says. “Are the streets narrow and dark? Is there graffiti and garbage all around? What do the bars and restaurants nearby look like? Do they seem like places where people hang around outside making a lot of noise?” She says Street View is the best substitute for a drive. It gives you a sense if it is a place where you’ll feel safe and comfortable. 

DISCLAIMER: This article expresses my own ideas and opinions. Any information I have shared are from sources that I believe to be reliable and accurate. I did not receive any financial compensation for writing this post, nor do I own any shares in any company I’ve mentioned. I encourage any reader to do their own diligent research first before making any investment decisions.

Christopher Elliott's latest book is “How To Be The World’s Smartest Traveler” (National Geographic). You can get real-time answers to any consumer question on his new forum, or by emailing him at