Destination Wednesday: Six Tips For Living Like You Own The Place

Photo credit: Chistian Holzinger via Unsplash.

By Sharyn Alden

There are more options than ever for people who love travel and crave a homelike experience. And one of the best options is one of the oldest: Renting a vacation home directly from the homeowner or their agent.

Home-rental sites like, and have made it easy for you to live like a local, at least for a little while — and often for a per-person cost that’s less than many hotels.

Before you jump headlong into property rentals, you need to know the ropes. It goes way beyond just picking out a place because you like how it looks online. Take my word for it; I’ve been renting vacation homes abroad for many years, and I always expect the unexpected.

Actually, the unexpected is de rigueur when you are moving into someone else’s home, though sometimes the unexpected is wonderful. A vacation home on Eleuthera Island in the Bahamas comes to mind. It was humbly described online, but turned out to be fit for an A-list movie star.

It’s only when things break the other way that the unexpected can be troublesome. But these situations are often avoidable if you simply do your homework.

I can’t emphasize that point enough. As with any online purchase, do your homework, and you won’t be borrowing trouble. In general, you’ll want to:

Look at the property in person, whenever possible. In an ideal world anyone could inspect a home’s views, location and condition first-hand before renting. Case in point: An oceanfront home I rented online showed magnificent views of nearby islands. The waterside views were as advertised; however, nothing was said about the sides of the property. No wonder: A cemetery was on the right and the house on the left was an arm’s-length away.

How can you avoid this? Barring house-shopping in person, ask the owner the questions that really matter to you. What’s the neighborhood like? How far to the beach/shopping/dining/the city/the country/attractions? What are the neighbors like? Loud or quiet? If you’re returning to a favorite destination, scope out rental homes in person the next time you’re there. It’s also acceptable to ask for additional pictures or a video tour if you want to see more.

Rent with a credit card. Credit-card charge-back protection can protect you against some problems. For example, the Fair Credit Billing Act requires credit-card issuers to remove a charge from your account for any service or product you bought but didn’t receive. With that said, a lot of vacation rental owners aren’t set up to take credit cards. Bottom line: Never ever send cash or a cash equivalent like PayPal to anyone you don’t trust. If the only way to pay is by a cash equivalent, leave a paper trail, even if it’s a bank transfer, cashier’s check or debit card.

Read the fine print. This should be a no-brainer, but it’s even more important when you’re making advance payments – and you’ll likely be making advance payments, since most rentals require a deposit to hold your home on the dates you request. Read the contract thoroughly; know what you’re paying for. Some sites might display a rental fee of $200/night, but in smaller print it may say you need to add $50 per person a night. So the total fee really could be upwards of $300/night. This may not be clearly stated on the listing.

Along with that, know the cancellation policies. When I had to cancel a reservation four weeks in advance after having paid the full $1,700 weekly fee, I was told I wouldn’t get any refund unless they could re-rent the property for the same time frame. That was not easily decipherable when I first reviewed the contract. Fortunately, the home was re-rented and I received a full refund in the mail; otherwise, I would have been stuck.

Maintenance and contacts. It’s a good idea to rent a home with a maintenance person or rental company on-call. Make sure that contact is available around the clock. I’ve had to call a contact person for everything from needing the wireless code to having to find another place to stay in the middle of the night because I was sharing my lovely log home with a variety of rodents and other small animals.

Protect yourself. On sites like VRBO, VacationRentals and HomeAway, you can add layers of fee-based protection. If the price of your vacation rental is $1,200, for example, you can add damage protection for $59 for $1,500 of protection, or cancellation protection for $54. If you worry whether the property is as advertised or even exists, you can add the Carefree Rental Guarantee for $39. This covers things like rental bankruptcy or foreclosure, damage-deposit refunds, identity theft, or – horrors if this ever happened to you – the property being double- or triple-booked!

Please Don’t Eat the Daisies. When I’ve forgotten to ask about something or it wasn’t pointed out because the odds of it becoming an issue are extremely obscure, I call it a “Please Don’t Eat the Daisies” moment, in honor of that madcap 1960 film of the same name.

In that movie, a family with four young, wild boys moves to a rundown country mansion complete with secret passageways and trap doors. When the mom (Doris Day, of course) returns home after being out for a little while, she’s stunned by what the kids did when the babysitter was in charge. Plenty of detailed babysitting instructions were left behind, but one thing wasn’t covered: Who’d have thought to mention it wasn’t okay for the boys to eat the daises?

Left-out information can break your vacation if you fall in love with photos of a home and don’t dig deeper when talking to the owner. (And yes, talk to the owner; don’t just email. A phone conversation can be very helpful in ironing out details.)

Here are some of my own “daisies” moments in vacation-home rentals – things not asked, not pointed out, and not joyful moments at the time.

  • At a beautiful wooded Scandinavian-style home, six of us knew we would share one bathroom on the first floor, and we accepted it. But nowhere on the listing did it state that the bathroom was a tight, walk-in-sideways, airplane-sized restroom. And the shower? It was in a separate thin closet the same size as the “bathroom.” This home, albeit very artsy with gorgeous landscaping, didn’t have many things you’d expect, like a banister leading up the windy, treacherous outside staircase.
  • In the heat of summer, a home rental that was advertised as “air-conditioned” by the breezes coming in off the lake a few yards from the home was nearly insufferable because of no cross-ventilation and no fans. The neighbors guessed our fate and brought over fans without asking.

One last thing: When considering property rentals, know your group. Most rentals only make economic sense if you’re traveling in a group; group travel leads to group dynamics, and group dynamics often lead to a court of law. Before you sign anything, make sure everyone in your group okays the property, agrees to the cost-split, and is totally on-board with the rental. This can take more time than finding the property and going on the vacation combined, so be ready.

And then get ready for the vacation experience of your life.

Sharyn Alden is a long-time travel writer with a media-relations business, Sharyn Alden Communications, Inc., based in Madison, Wis.

Editor’s Note: A rental vacation can be super-memorable. Protect it with ExactCare, comprehensive-yet-affordable travel insurance from Berkshire Hathaway Travel Protection. Get it here.