1 Pick Your Approach Determining whether to use a rental service, and what type—a big agency with thousands of listings or a smaller one with a select few— is essential. Your choice will depend on how much inventory you're willing to wade through and how much assistance you require during both the selection process and your stay. To help you decide, we've sussed out the benefits and drawbacks of each method (see "Agent vs. Free Agent," right). We've also listed our favorite rental companies in "The Global Guide to Villa Rentals" (starting on page 208). And if you'd rather avoid rental companies altogether, you can always turn to a travel agent.
2 Plan Ahead Although most rental companies recommend that you book five to eight months ahead of time, highly popular properties can fill up a year in advance, especially European villas during July and August and Caribbean properties during the winter holidays, so plan accordingly.
3 Set a Budget Villa rentals can run anywhere from $1,000 to $100,000 a week, but don't let the high prices send you into sticker shock. Consider that a $25,000-a-week fully staffed eight-bedroom villa comes out to only $450 a night, per couple. In certain destinations, this price is unbeatable. On the flip side, a $5,000-a-week unstaffed property in a lackluster setting might leave you longing for the perks and location of a hotel. When you're determining your budget, take into account how much you value aesthetics, location, and additional services (housekeeping, cooking, concierge), and identify what, if anything, you are willing to sacrifice.
4 Dig for Details When assessing a house, use photographs as the jumping-off point for specific questions. Ask as much as possible about the exact surroundings (e.g., if there's a major highway out front or a construction site next door), how close (and who) the neighbors are, where the nearest grocery store is located, how long it takes to walk to the beach or drive to and from the airport, and whether you'll need a car to get around. Don't forget to ask about the views, room dimensions, the last time the property was remodeled, which rooms get the most sunlight, and whether there is an English-speaking contact nearby to handle any unexpected problems. The more you know before you book, the fewer surprises you'll have upon arrival.
5 Ask for References No matter how good the agency, agent, or owner, each is still trying to sell you a product. Request a list of references who have stayed at the property. They can give you an unbiased opinion about both the company and the villa itself.
6 Get It in Writing Once you've chosen your rental, make sure you receive a contract detailing all the specifics of the negotiation (read it carefully). Most agencies send one as a matter of course, but you might need to prompt an individual owner to provide a contract that reflects all of your negotiations.
7 Protect Yourself Buy trip insurance, which usually costs between three and five percent of the vacation's total value. Most villa rental contracts require you to pay in full 30 to 90 days prior to arrival. If anything should happen between the time your credit card is charged and the moment you're handed the keys—be it a natural disaster or a personal one—insurance will help you reclaim your money.