Image: Villa Chianti Classico in Tavarnelle Val de Pesa, Florence (Italy)
© www.parkervillas.com
The thrill of experiencing a foreign culture at your pace and on your terms is a prime reason to consider a rental. The Villa Chianti Classico in Tavarnelle Val de Pesa, Florence, Italy, rents for $10,685-$18,640 weekly depending on season.
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updated 8/8/2007 8:16:47 PM ET 2007-08-09T00:16:47

You may have stayed in your share of five star hotels, but there is nothing quite like renting a villa. A “villa” can be a castle in Scotland with its own 18-hole golf course, a multi-roomed mansion overlooking the Mediterranean or a beachfront retreat in St. Lucia. If you've glimpsed hilltop aeries and beach houses in Mexico or the Caribbean, or spent time in the French or Italian countryside (even vicariously through, say, Merchant-Ivory movies) it's a safe bet that you've fantasized about what it would be like to rent a property there.

Why rent a villa? In a word, romance. The thrill of having a luxurious home of your own for a week or more is a prime reason to go the villa route. Many villas are historic homes in fabulous locations. And in your own home, you awaken to your own clock, not a hotel's. You fall into an easy routine of visiting food markets and shops, particularly in countries like France and Italy, which gives you a way to integrate with the culture and experience the country in a manner that the average tourist never really does.

Space is also a reason to rent and a godsend for families or groups of friends. Having a living room, a dining room and multiple bedrooms, as well as a garden and perhaps a swimming pool, means you can relax without getting in each other's way. Since every rental comes with a kitchen or kitchenette, dining out is an option, not a requirement. If you're near a town, you can eat lunch or dinner out or enjoy leisurely meals at home. In fact, booking a villa is the antithesis of that classic vacation where you rush around to cathedrals, restaurants and museums. Villa time is downtime.

In most cases, renting a villa will run you less than a comparable hotel. Even at the high end, a four-bedroom luxury villa with pool in Tuscany like “Belvedere” from Homes Away rents for $12,700 per week. For eight people, that comes out to $1,587.50 per person, per week, or $226 per night. That's far less than a four or five star hotel in the same region.

You can start your search for the perfect villa online. There are companies like WIMCO that cover the Caribbean as well as Europe, and others such as LaCure that extend their reach from Europe to Central America, Mexico and North Africa. There are also specialists like The Parker Company, which concentrates solely on Italy. At Home in France has a wide range of affordable rentals in that country. And the Toronto-based Homes Away, which was founded by ex-Butterfield & Robinson executive Dan Legault, is less a rental agency than a tour operator. Each of their properties comes with a local host who acts as a concierge. If you want go truffle hunting in Umbria with a local farmer, take a bike ride to Bonnieux and Menerbes, or keep a private chef at the villa for the duration, they can arrange it.

"We field, on average, about a dozen calls from each client about the houses, the regions, and matching a house to them," says Legault of Homes Away. "Our clients want that gentle, refreshing and inspiring sense of 'living' in a quietly beautiful and culturally rich part of the world. They expect, as a matter of course, to have things come off without a hitch, and the house to be a lovely, wonderful extension of the region."

But for do-it-yourselfers, Web sites such as Vacation Rental by Owner (vrbo.com) offer thousands of properties directly through the owner. While it's obviously potluck, you can find real gems this way. And the costs are invariably lower, since there's no booking company to act as middleman.

Image: The Villa Ambrosia in Montepulciano, Siena, Italy
© www.parkervillas.com
If you want every last detail taken care of, get a rental from Homes Away. Each property comes with a local host who acts as a concierge — whatever you need, from wine tastings to tickets to the Palio, they can arrange it. The Villa Ambrosia in Montepulciano, Siena, Italy, rents for $7,955-$14,775 weekly depending on season.
But while you're searching for the rental of your dreams, don't be blindsided by wonderful photographs and rhapsodic prose. Instead, run through a checklist of amenities that are important to you and be prepared to read a little bit between the lines. Question how far it is from Florence; if there's a grocery store nearby; or if it’s suitable for small children? Every good rental agent should provide a list of amenities that are included with the rental, from linens to a washer and dryer. It's important to know how frequently the villa will be cleaned, and what the Internet service is like. It's essential to have a nearby contact—preferably someone who speaks English—in case a pipe bursts or the stove won't work.

Renting a villa in Europe will likely mean that it's necessary to rent a car as well. If you don't feel comfortable with the thought of driving in Italy, for example, or driving on the left in England, try to find a rental that's in a village accessible by public transportation.

Image: www.lacurevillas.com
© www.lacurevillas.com
Many villas are wonderfully remote, but that means that it's necessary to rent a car as well. If you don't feel comfortable with the thought of driving in Italy, St. Bart's or on the left side of the road in England, try to find a rental that's in a village easily accessible by taxi or public transportation.
When it comes to the amenities of a given property, hold your American expectations in check. Bathrooms can be remarkably simple and plain—not necessarily luxurious—regardless of how much you're paying for a house. As for sleeping arrangements, they're often inflexible and predicated on at least some guest rooms with single beds. Even a larger residence with multiple bedrooms may only have one queen-sized bed. And when a listing states that the property sleeps six, don't assume there are three bedrooms. There might be two bedrooms, plus two sleeper sofas. To their credit, most companies will spell this out clearly, but do read descriptions carefully.

It's also smart to choose your season carefully. The Caribbean in the fall offers good value but also means running smack into hurricane season. And in places like Tuscany in August, it can get beastly hot, not to mention crowded. European rentals are less pricey and the towns less crowded in April, May, September and October. Late spring and late fall also work well for the Caribbean and Mexico. But don't push shoulder season too far. Once you get into mid-October in Provence, the chilly mistral wind arrives. As for May in Scotland, it feels more like March in the northeastern United States.

Oh, and one last thing to consider. If you're the type who likes someone else to make the perfect bed, lay out breakfast under the pergola, and stoke the fire in the great room, think twice about renting a villa unless you plan to hire a staff for the duration of your rental. Otherwise, you might be happier in a full service hotel.

But if you're someone who looks forward to preparing a lunch under the chestnut trees, buying wine from a local farmer and doing nothing more strenuous than the backstroke even though ancient ruins beckon, then a villa rental might be in your future.

Here's what you need to know to rent the villa of your dreams.

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