Renting a reliable vacation home isn't easy.

And not just because there are a seemingly endless number of rental resources to turn to -- everything from local sites that list a few condos to big listing services like HomeAway ( or VRBO (

For me, it's the politics.

This summer, for example, I told my mother that I planned to rent a condo on the beach. Within two days, my sister and brother had invited themselves over, boosting our numbers from five to more than 30.

A rental home can save you a lot of money when you're on vacation, as I pointed out in an earlier column. But this one would almost certainly cost me a lot more.

There are an estimated 1 million vacation rentals in the United States, roughly half of which are available to the general public, according to numbers from The National Association of Realtors and FlipKey ( A recent PhoCusWright study estimated vacation rentals were a $24.3 billion-a-year market, while a Ypartnership survey suggested interest in renting a home was on the rise, with 14% of leisure travelers saying they stayed in one in 2009, up from 11% a year earlier.

Renting a home for 30 isn't like booking a hotel room, or even a vacation cottage for a family of five.

"The consistent challenge we hear from travelers is predictability," says TJ Mahony, the chief executive of FlipKey, a vacation rental site owned by TripAdvisor. "People tend to know what they are going to get from a hotel, but can have anxiety over the quality of a vacation rental."

I asked experts to identify the biggest challenges when renting a home. Here's what they told me:

1. Knowing what you want. Prioritize your rental. That's the advice of Teresa Bell Kindred, a blogger and frequent home renter. "You are going to pay more for certain things. Decide what is really important to you," she says. Her family loves the ocean, so they don't mind paying more to be right on the beach. But if you don't mind being a few blocks away from the water, you can save money. Be sure you stay within your budget. "If you spend all your money on rental property and can't afford groceries you may get hungry before you get back home," she warns.

2. Timing your purchase. If you're in town for a special event, like a sports tournament or festival, it's never too soon to book a vacation rental. "Vacation rentals are more scarce than hotels and great vacation properties are even scarcer," says Chris Brusznicki, the chief executive of GamedayHousing (, a site that specializes in rentals for sports events. But if there's no reason to be in town, you can run down the clock. One terrific new site that allows you to bid on "last-minute" vacation rentals is a site called PackLate.

3. Finding out what you're renting. It probably goes without saying that you need to do your due diligence on a rental. "Do your homework," says Sylvia Guarino, who owns a rental home on Sanibel Island, Fla. (one of my favorite places) and a member of Second Porch (, a Facebook application that connects vacation rental owners and vacation guests. "Vacation rental guests sometimes get too focused on getting a deal, and not focused enough on getting the information that they need, or authenticating the property. "How do you authenticate a property? Look at every piece of information available to you, including the owner's website, the vacation rental site, online reviews and what you find on social networking sites, like Facebook. Be sure the property is in good shape, is as represented and isn't in foreclosure.

4. Finding out who you're renting from. "Research the owner, not just the home," says Kelly Hayes-Raitt, who owns a rental property in Santa Monica, Calif. She includes a link to her website and biography in every correspondence with potential guests, "not just so they realize they are supporting my work with refugees, but so they learn they are dealing with someone who has been active in her community for 30 years and not likely to cheat them," she says. Not every owner is as forthcoming as Hayes-Raitt, but if someone is reclusive, it might be a warning sign.

5. Determining if the rental is part of an association or destination. That can make a big difference, according to Jon Ervin, a spokesman for the Cottage Rental Agency in Seaside, Fla. "Imagine you rent from Mr. and Mrs. Jones -- nice enough people, but what if your air conditioning quits or some other concern arises?" he asks. "You most likely are going to have to work through the issue for your entire stay." Not if your rental is part of an association. There's someone on call to help in situations like that. My family rented a home at the WaterColor Inn & Resort in nearby Santa Rosa Beach, Fla., during the Christmas holidays, and we found that to be good advice.

6. Becoming a power user. For example, VRBO allows you to filter search results by area, bedrooms and the number of people it can sleep. That helped Kellie Pelletier find a vacation rental in Charleston, S.C., for her family. VRBO also shows which homes are available on your preferred dates. "So I didn't waste my time researching and contacting houses that were already booked for my week," she says. Pelletier knows a thing or two about being a power user. She used to work for Kayak (, the booking site. "House rental sites are years, if not decades, behind other travel sites," she complains. "Please, won't somebody launch the Kayak of rental house sites?"

7. Avoiding group-think. Extended families like mine should be broken up into smaller housing units, such as adjoining condos, as opposed to fitting them into one house. It gives everyone more privacy and is easier on the finances, because you don't have to argue over the bill at the end. "Sometimes a big house works for some families," says Carol White, who runs a website about road trips. "But not others."

8. Reviewing the contract very carefully. You're not checking into a hotel; this is more like renting an apartment. Watch for contract language, such as cleaning options. Frank Discala, who owns a rental property in Nantucket Town, Mass., gives his tenants two options: either clean up after themselves, "Or they can leave the place without cleaning up and lose their $500 deposit," he says. "Ouch! No one has ever taken that option." (Discala knows about contracts; he's a lawyer.)

9. Staying flexible. Remember, you're renting an apartment or house -- not a room in a hotel. "Some things may go wrong," warns Pauline Kenny, a vacation rental expert who runs a site called Slow Europe ( "The plumbing may stop working, the kitchen stove runs out of gas. Some things may not be perfect -- you bump your head repeatedly on that low doorway, the couch is orange, the parking space is almost impossible to get into." That's life in a vacation rental. "Suck it up and live with it," she says.

Needless to say, tenting a vacation has its challenges. "The process for finding a vacation rental home is more involved and sometimes even difficult," says Christine Karpinski, a director for "You have to not only search for the home, but you also have to e-mail to inquire whether or not it is available and for a full quote. Sometimes the process can take a couple hours and sometimes it can take a week of back-and-forth with the homeowners. But the reward at the end is wonderful."

I hope she's right. I'll let you know what happens this summer.

Christopher Elliott is the ombudsman for National Geographic Traveler magazine and the host of "What You Get For The Money: Vacations" on the Fine Living Network. E-mail him at

(c) 2010 Christopher Elliott. Distributed by Tribune Media Services, Inc.