1 Choose a destination Consult guidebooks and visitors bureaus, ask friends for their input and recommendations, and do all the research possible to figure out where you'd like to rent. There are hundreds of thousands of vacation rentals available around the globe, so be as specific as you can to winnow down the choices.
2 Weigh your options Start by skimming the rental listings on a few websites for the location you've chosen (see Sites to Search on page 49). Note the sort of properties available, what you get for the money, and the typical rental policies, such as minimum-stay requirements. Compare your results with the nightly lodging rates charged by local hotels, real-estate agents, or management companies, which are often posted on the same sites. And then be honest with yourself: Are you really OK without maids, room service, an on-site restaurant, or hotel amenities? Decide which type of accommodations makes the most sense for you.
3 Rank your priorities Most sites let you sort listings according to the number of bedrooms, the price, and other variables, which can be a huge time-saver in finding what you're looking for. Don't be too rigid in defining your search, though—you may be willing to have one less bedroom if the location is exactly where you want. Leave yourself some wiggle room.
4 Contact the rentals on your short list First, ask if your desired dates are free. Even if they appear to be available on an online calendar, the site might not be up-to-date. Be sure to ask for the exact address of the rental as well as the layout of the property, more photos, and any other details you're curious about. Some owners have separate sites where they have more information about the lodging than what appears on the rental site. E-mailing is the best method for the first contact; give the owner 24 hours to answer. If it takes much longer than that, he or she could be just as slow to respond if there's a problem.
5 Do your own research Compare the listing with what you find when you plug the address into the satellite view on Google Maps or Google Earth. Scope the area for nearby attractions both bad (factory complex) and good (local park). The property might be three blocks from the beach as stated, but there could be a four-lane highway in between. Do a regular Google search with the rental's address or the owner's phone number in quotes. The results will reveal whether the property is listed at more than one website—an indication that the owner is serious about renting—or only listed on a single site. Reputable owners often run multiple listings for their properties. Your Google search might also bring up complaints, which you'll want to review carefully.
6 Call your top choice(s) Be candid and up-front about your expectations and your concerns: Tell the owner that you have kids, that you want to walk to the market every day, or that your husband is a light sleeper and needs a quiet neighborhood. Ask specific questions like "Where do you think the baby should sleep?" The answer you get, such as "Not in the front of the house, because traffic might wake her up," may well be revealing. You could handle these queries via e-mail, but it's easier to get a sense of a person over the phone. Be wary if he or she is evasive, impatient, or curt. Also, be cautious when someone seems to be telling you exactly what he or she thinks you want to hear. Conscientious owners want to find good matches for their properties and won't be so eager to rent to just anyone.
7 Check references A lot of websites have pages for renters to post comments on, but the bulk of properties have no reviews at all. The few reviews that are there tend to be positive, which is unsurprising considering that owners can generally edit or delete comments at will. Vacation-home owners are also in control of supplying references, so it's difficult to get an unbiased opinion, but ask anyway. And then call those references rather than using e-mail, because people tend to open up more in phone conversations than online.
8 Try negotiating If the listing says the owner only rents on a monthly or biweekly basis, ask if he or she can make an exception. Most owners are willing to deal at least a little bit, especially if your dates are coming up soon. (Then again, some owners raise their prices at the last minute.) Either way, it's fair to ask for at least 10 percent off if you're arriving within two weeks. Think back to the browsing stage: Did most rentals offer a seventh night free or waive the cleaning fee for guests staying more than five days? Ask for the same.
9 Know your different payment options If you're not comfortable with the owner's suggested payment procedure, request an alternative method. Credit cards are easiest and offer renters some level of protection, and more and more vacation- home owners in North America accept plastic via PayPal (an online payment service that keeps your credit card and banking details hidden from the recipient). For overseas rentals, you're more likely to be asked for a bank-to-bank transfer (see the sidebar at left). If you don't want the extra hassle or costs, and the owner is game, try to hold the dates with a credit card or a partial deposit via check, and then pay the rest in cash on arrival. Most owners are happiest with cash, anyway. Never—ever—pay with Western Union or a money order. They're virtually untraceable, so in the rare case of a scam, your money could be gone for good.
10 Read the contract Make sure everything is clearly spelled out before putting any money down. Start with the basics. Check dates and dollar amounts. Home owners will often draw up all their rental contracts themselves, and mistakes can happen. Also double-check that you're renting the correct property. After searching through hundreds of listings, it's easy to get mixed up. Finally, keep a copy of the contract for your records.
11 Buy insurance Most vacation-rental cancellation policies are very strict, which is understandable considering they don't have a walk-up business as hotels do. The later you cancel, the stiffer the penalties. Buying travel insurance is an especially good idea in these situations because you have to pay the full amount up-front; if something happens and you can't travel, you could lose most or all of your money. Compare travel insurance policies at squaremouth.com or insuremytrip.com.
12 Prepare for your arrival Make sure you know the procedure for getting the keys. Some owners mail them out; others have a code to unlock a key box on the door. You should also ask the owner for tips on restaurants, babysitting services, farmers markets, grocery delivery, shopping, hiking, or whatever sorts of activities you're interested in. Many vacation-home owners have advice typed up and waiting for you at the rental house, so ask them to e-mail you a copy of it in advance. Don't forget to print out the directions, the owner's phone number and e-mail address, and the number to call if there's a problem with the property—the owner should have someone available 24/7 in case of emergency. E-mail yourself the same information so you can still get a hold of it even if you misplace the hard copy en route.
13 Go in with realistic expectations No matter how much scouting you do beforehand, there's always some sort of surprise when you open the door. Rentals are not hotels, and no property is perfect. Your best bet is to embrace the quirks: Toasters break. Wallpaper can be ugly. Beds may be too firm or too soft. Give the owner the benefit of the doubt, and don't let minor problems ruin your vacation.
14 Peruse the log Check out the guest log and read through the comments from former visitors. They'll clue you in on what people loved (or hated) about the place, and they can also offer good suggestions on what to do while you're in the area.
15 Got a problem? Call immediately Contacting the owner as soon as possible is the best—and often the only—way to resolve an issue. Be cordial, but be firm. The problem doesn't have to be major to merit mentioning; let someone know about the crack in the bathroom window or the stains on the living room rug. At the very least, you want the owner to know you weren't responsible for them. It's also OK to call if you can't find beach chairs or the promised lobster pot. If you need an item that's not in the house, ask if you can be reimbursed if you buy one and leave it there. Most owners want guests to have enjoyable stays, if only for recommendations and return visits.
16 Leave the place in good shape Follow the instructions in the contract and those detailed at the house. That might mean taking out the garbage or sweeping sand off the deck. (Not doing so will likely inconvenience the next renters more than the owner.) Share your insights with a review in the log and on rental websites. Then do the same for the owners: Send an e-mail thanking them and giving them feedback.
17 Get your deposit Call if your deposit is not returned by the agreed-upon time, and if the deposit is less than you expected, get an explanation immediately. (The discrepancy could be due to a cleaning fee or a tax you overlooked.) If there's a dispute or the owner doesn't return your calls, contact the listing site. Its reputation is at stake, and it may be willing to mediate. Small-claims court is a last resort.