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. And yes, there are a few vacation rental tips even the experts don’t know.

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 upfront,” 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

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.

Posted in On Travel Tagged , , , , , , ,

Christopher Elliott is the founder of Elliott Advocacy, a 501(c)(3) nonprofit organization that empowers consumers to solve their problems and helps those who can’t. He’s the author of numerous books on consumer advocacy and writes weekly columns for King Features Syndicate, USA Today, and the Washington Post. If you have a consumer problem you can’t solve, contact him directly through his advocacy website. You can also follow him on Twitter, Facebook, and LinkedIn, or sign up for his daily newsletter.

Underwritten by

Elliott Advocacy is underwritten by Global Rescue

Global Rescue is the world’s leading provider of medical, security, evacuation and travel risk management services. Founded in 2004, Global Rescue has exclusive relationships with the Johns Hopkins Emergency Medicine Division of Special Operations and Elite Medical Group. Global Rescue provides best-in-class services that identify, monitor and respond to client medical and security crises. Learn more about Global Rescue.

Elliott Advocacy is underwritten by battleface

At battleface, we deliver insurance that doesn’t quit when circumstances change. We provide specialty travel insurance services and benefits to travelers visiting or working internationally, including in the world’s most hard to reach places. Currently selling in 54 countries and growing, our mission is to deliver simple solutions to travelers worldwide heading out on their next adventure.

Elliott Advocacy is underwritten by Pomchies

Pomchies makes an array of functional products out of swimwear material -- from hair scrunchies to luggage tags to headbands and more. Forced to pivot in 2020, Pomchies started manufacturing masks and changed the entire trajectory of the business. With over 4 million masks in circulation and a strong demand, Pomchies is now one of the most popular mask companies in the United States. To view the entire product line or to learn more, visit

Elliott Advocacy is underwritten by World Nomads

World Nomads travel insurance has been designed by travelers for travelers, to cover your trip essentials. Even if you run out of travel insurance or leave without it, World Nomads can cover you. We don't just keep you and your family protected, with us, you'll travel smarter and safer. Get more information at World Nomads.

Elliott Advocacy is underwritten by Generali Global Assistance

Generali Global Assistance has been a leading provider of travel insurance and other assistance services for more than 25 years. We offer a full suite of innovative, vertically integrated travel insurance and emergency services. Generali Global Assistance is part of The Europ Assistance (EA) Group, who pioneered the travel assistance industry in 1963 and continues to be the leader in providing real-time assistance anywhere in the world, delivering on our motto – You Live, We Care.

Elliott Advocacy is underwritten by Seven Corners

Seven Corners has helped customers all over the world with travel difficulties, big and small. As one of the few remaining privately owned travel insurance companies, Seven Corners provides insurance plans and 24/7 travel assistance services to more than a million people each year. Because we’re privately held, we can focus on the customer without the constraints that larger companies have. Visit Seven Corners to learn more.

Elliott Advocacy is underwritten by Sodexo North America

Sodexo North America Sodexo North America is part of a global, Fortune 500 company with a presence in 80 countries. Sodexo is a leading provider of integrated food, facilities management and other services that enhance organizational performance, contribute to local communities and improve quality of life for millions of customers in corporate, education, healthcare, senior living, sports and leisure, government and other environments daily. Learn more at

Elliott Advocacy is underwritten by Travelex Insurance Services

Travelex Insurance Services is a leading travel insurance provider in the United States with over 55 years combined industry expertise of helping people dream, explore and travel with confidence. We offer comprehensive travel insurance plans with optional upgrades allowing travelers to customize the plans to fit their needs. Compare plans, get a quote and buy online at

Elliott Advocacy is underwritten by Allianz Travel Insurance

The Allianz Travel Insurance company has built its reputation on partnering with agents all around the world to provide comprehensive travel insurance for their clients. Contact Allianz Travel Insurance for a comprehensive list of coverage.

Elliott Advocacy is underwritten by Fareportal

Fareportal’s portfolio of brands, which include  CheapOair and  OneTravel, are dedicated to helping customers enjoy their trip. Whether you want to call, click, or use one of our travel apps, one thing is clear: We make it easy to take it easy.

Elliott Advocacy is underwritten by

An independent provider of low cost CDW/LDW insurance for use with rental cars. Up to $100,000 cover with no deductible. Policies available on a per day, per trip or per year basis. Also works with overseas rentals. Try  Insuremyrentalcar.comnow.

Elliott Advocacy is underwritten by Mediacom Communications

The nation’s fifth-largest cable operator, serving the smaller cities and towns in the Midwest and Southern regions of the United States. We are a high-performance broadband, entertainment, and communications company that brings the power of modern technology and quality customer experience to life inside the connected home by combining ultra-fast gigabit speeds with personalized local and over-the-top entertainment choices that fit your lifestyle. Details at

Elliott Advocacy is underwritten by Arch RoamRight

Arch RoamRight is one of the fastest growing, most-highly rated travel insurance companies in the United States. Travel advisors love working with us, and travelers feel protected with our trip cancellation and travel medical insurance coverage. We also make it easy to file a claim online with our fast, paperless claims website. Learn more about RoamRight travel insurance.

Elliott Advocacy is underwritten by VisitorsCoverage

VisitorsCoverage is one of the world’s most trusted providers of travel insurance for millions of global travelers in over 175 countries. Working with top-rated travel insurance partner providers, VisitorsCoverage’s award-winning search, compare and purchase technology simplifies the travel insurance process and finds the best deals for the coverage you need to explore the world with confidence. Get insurance for your next trip at VisitorsCoverage.

Elliott Advocacy is underwritten by MedjetAssist

Medjet is the premier global air-medical transport, travel security and crisis response membership program for travelers. With a MedjetAssist membership, if you become hospitalized more than 150 miles from home, we will get you from that unfamiliar hospital all the way home to the hospital you trust. All you ever pay is your membership fee. MedjetHorizon members add 24/7 personal security and crisis response benefits. readers enjoy discounted rates. Travel safer with  MedjetAssist.

Elliott Advocacy is underwritten by Southwest Airlines

The mission of Southwest Airlines is dedication to the highest quality of Customer Service delivered with a sense of warmth, friendliness, individual pride, and Company Spirit. We are committed to provide our Employees a stable work environment with equal opportunity for learning and personal growth.

Elliott Advocacy is underwritten by makes it fast and easy to compare and buy travel insurance online from top rated providers. Our unbiased comparison engine allows travelers to read reviews, compare pricing and benefits and buy the right policy with a price guarantee, every time. Compare and buy travel insurance now at

Elliott Advocacy is underwritten by Travel Leaders Group

Travel Leaders Group is transforming travel through its progressive approach toward each unique travel experience. Travel Leaders Group assists millions of travelers through its leisure, business and network travel operations under a variety of diversified divisions and brands including All Aboard Travel, Andrew Harper Travel, Colletts Travel, Corporate Travel Services, CruCon Cruise Outlet, Cruise Specialists, Nexion, Protravel International,, Travel Leaders Corporate, Travel Leaders Network and Tzell Travel Group, and its merger with ALTOUR. With more than 7,000 agency locations and 52,000 travel advisors, Travel Leaders Group ranks as one of the industry’s largest retail travel agency companies.

Elliott Advocacy is underwritten by Travelers United

If you’ve been mistreated by the airlines, Travelers United is your voice in Washington. Join the #1 travel advocacy organization working with Congress to improve and protect travelers. Plus, get $400 of annual benefits you can use for travel for only $29/year. Add your voice to ours. Make travel better.  Join today.

Elliott Advocacy is underwritten by Generali Global Assistance

Generali Global Assistance has been a leading provider of travel insurance and other assistance services for more than 25 years. We offer a full suite of innovative, vertically integrated travel insurance and emergency services. Generali Global Assistance is part of The Europ Assistance (EA) Group, who pioneered the travel assistance industry in 1963 and continues to be the leader in providing real-time assistance anywhere in the world, delivering on our motto – You Live, We Care.