
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.com or VRBO.com.
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 5 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.com. 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 percent of leisure travelers saying they stayed in one in 2009, up from 11 percent a year earlier.
Renting a home for 30 isn’t like booking a hotel room, or even a vacation cottage for a family of 5.
“The consistent challenge we hear from travelers is predictability,” says TJ Mahony, the chief executive of FlipKey.com, a vacation rental site. “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.com, 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 site, 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 Web site 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.com 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.com, 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 Web site 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 HomeAway.com. “You have to not only search for the home, but you also have to email 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.
(Photo: red dahlia/Flickr Creative Commons)

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Now if we could only hear the flip side! How does one find responsible, caring renters for a cherished family cottage? We plan to start renting ours – a beauty on Lake Michigan – a few weeks a year but we’re obviously leary of renting to total strangers.
Marge: to answer your question, you are perfectly entitled to interview potential tenants as well. And don’t think they’re be put off because if they are, you really don’t want them anyway. I have rented properties in France and have found that if you speak to people, they understand your property is special and not simply a flop house furnished solely to generate rental income.
And BTW – some have my worst experiences have been renting to friends (or friends of friends). SOME feel they can take advantage because of “friendship.”
Always draw up a contract specifying conditions and how many people may occupy the premises.
And Chris – my teeth shutter when I hear the words a vacation for 30 people! Be still my heart!
Thanks for a well-written and informative article. I want to point out that if you are renting from a licensed rental company, in most states they must be licensed real estate companies, which means they have to escrow all monies until the guest departs, whereas individual owners have no legal requirement to do so, so if you rent from an Owner, be sure to only pay by credit card, or even better, by PayPal, which doesn’t require giving your credit card info to a stranger.
Also, if you are the property owner, and want guests to be sure to repect your house as a “home”, a few well-placed family photos help people to realize that this is a home, not a “rental property”. Also, a guest book for people to sign and leave memories of their stay, plus a notebook full of local restaurant, shopping and activities helps guests appreciate the hospitality you are sharing.
And last, a great new source to locate professionally managed beach houses, beach condos, and luxury mountain cabins in the Southeast USA can be found at BestSoutheastRentals.com.
Hope this helps,
David in Dauphin Island, AL
As someone who has been on both sides of the transaction, it’s the responsibility of both parties to do their homework. And if it’s a bad fit, the owner has to be willing to say no. Less short-term gain, but also less pain that way. This is a great checklist. 30 people though? That’s a royal coordination pain.
Great article! Once you have found a reliable site or agency it turns out to be quite easy! For me that has been the clue! Since I doscovered and tried guesthousenetwork.com my vacations are all about enjoying!
I have been in the B&B business for over 12 years and in the vacation rental business for 5. My guests have become friends and have taken very good care of my homes. They are all welcome to return.
But I also live in the town where my rentals are and I’m on call 24/7 if there are problems. So for those who are looking at out of town owners, be sure the owner gives you the name of a local person to call in case of problems. AND the owner should give you her/his number in case of problems so he/she is aware of them and can make sure the problems are solved quickly,.
As someone who has rented vacation rentals and owns VR property which we manage ourselves I would like to see our industry become more efficient on the booking side but keep the personal touch of renting a VR. I feel so passionate about this that I and others have developed a management tool for VR owners that not only saves them time but also results in faster response to the guest, accurate calendars, an immediate response when dates are taken and the ability to pay by credit card in a very secure fashion. Sure, we expect to make money at this business but we also have an objective to improve the process for owners and guests. http://Www.snapvr.com
Vacation rentals are GREAT alternative to hotels. I only travel by way of vacation home! There are so many fantastic sites out there that make finding the perfect rental super easy. One site I came across, that I actually really like, isMetroFlats.com. Check these guys out, the site looks very easy to use and even lets users post their own vacations homes/properties.