Heaven For Rent The FORTUNE guide to finding the perfect villa.
By Donna Heiderstadt

(FORTUNE Magazine) – The Web has made browsing for villas a cakewalk. Dozens of specialists post listings for thousands of properties, from simple country homes ($500 per week) to no-expense-spared estates ($325,000 per week--and it gets you the entire island).

But the Web is a double-edged source. There's just too much out there. And for all its escapism, a villa rental is a serious endeavor, requiring both a contract and a hefty financial commitment. "You can't check out," cautions Edward Marquis of International Chapters. "And it's already been prepaid."

Expedia, Travelocity, and Orbitz make nothing of booking a hotel room without speaking to a person. Can a villa rental be equally impersonal? Should it be? Just seven of the 25 companies we contacted allow online booking, and even they don't encourage it. "A few little pictures can't tell you what you need to know," scoffs Marquis. Villa Network's Jim Duggar agrees: "We will not book a property without talking to the client."

Of course, each hand in the pie (owner, local management company, and U.S. rental agent) tacks on a commission, but trying to cut out the middlemen is rarely a good idea. You'll have little assurance about whom you're dealing with, and you'll forfeit the protection and clout of the rental agency should you encounter a problem.

So browse online, then pick up the phone. The agent is trained to help you find the property that best meets your needs. And, more important, to sense whether a rental--which in all but the most luxurious, fully staffed houses requires a certain affinity for independence--is really right for you. Says Suzanne Pidduck of Rentvillas.com: "I've actually told people I think it might be better for them to stay in a hotel."

Before You Book: 20 Questions

1. How long have you been in business? Don't be shy about probing a company's background (many post details on their Website) and reputation (some will offer references from former renters, travel agents who've booked clients with them, or tourism offices).

2. What will my budget get me? "Villa" is essentially a fancy word for "house"--and what you get can vary widely. Do a little research before you call. "That way you won't be oversold," says Peter Collard of Villa Leisure. "Most of our properties fall in the range of $100 to $500 per person, per night," adds Collard, who handles villas in the better and luxury ranges. But ask anyway, and you may discover that you'll get more house--or a fully staffed one--on a different Caribbean island or in a lesser-known region of Italy or France. Obviously, maximum capacity delivers the best rate. If you like a property but can't fill a fourth or fifth bedroom, ask whether the company offers reduced rates for partial occupancy--some do.

3. Has anyone there visited the property? Inspection is key to knowing a villa's assets and shortcomings. If your agent hasn't seen the property, ask to speak with someone who has. The owners and/or rental agents at many small-to-medium villa-rental companies (150 to 400 properties) claim to have seen about 80% to 100% of the properties they represent. "Unless you've inspected it," says Collard, "you shouldn't offer it." Larger villa-rental companies--with inventories from 500 to 6,000 properties--often rely on reports from local management firms.

4. When were the photos in the catalog and/or on the Website taken? More-up-to-date photos can be an indication that the property has been inspected recently. Ask for as many photographs as you can get. At minimum: several exteriors, the living/dining areas, the master bedroom, and one or two other bedrooms. Be wary of photos taken at night or in "staged" lighting, as well as tightly framed closeups--the photographer may be trying to hide something.

5. What are the rental terms, payment requirements, and cancellation policies? Most companies require a deposit of 20% to 50% upon booking and full payment 60 to 90 days before the rental date. Understand your obligation--and what you'll forfeit if you cancel--before you send a deposit.

6. When are the scheduled arrival and departure times? The standard weekly rental is from Saturday to Saturday, with arrival in the late afternoon on the first Saturday and departure before 10 a.m. on the following Saturday. But policies vary.

7. How and when do I get the keys? Some companies supply directions to the property, where you're met by the caretaker, key holder, or a representative from a local management company. Others greet you at the airport. Ask about the options--and any extra costs.

8. Is there a local English-speaking contact? Plumbing backs up, roofs leak, appliances malfunction--who you gonna call?

9. Is there a local concierge service? Some companies that specialize in high-end properties provide a local host to help with restaurant reservations, bike rentals, pantry stocking, etc.

10. What will the extra costs be? These vary greatly. At many properties extra costs are negligible (food, phone calls). Others come with a housekeeper, while those that don't may have access to one for a fee. Select villas are fully staffed, including a chef. If not, you may be able to hire a local chef for part or all of your stay. Phone calls, electric usage (especially in Europe where power is often allotted), and heat all generally incur added charges.

11. Does the property have any quirks? There's no cookie-cutter condo neutrality in a villa rental. Mario Scalzi of the Parker Co. cites "800-year-old stone steps that are uneven and worn down like St. Peter's toe at the Vatican" as a "minus" at some Italian properties--a fact detailed with warts-and-all candor on his company's Website.

12. Will we be the only guests on the property? Some rental villas, mostly in Europe, are part of larger estates or are one of several multi-room dwellings with-in one large country house. This means you may share ceilings, floors, and walls--as well as the grounds and pool--with other guests.

13. How close is the nearest neighbor? Don't rely on the photographs. "We had beautiful photos of one house, but all shot from one angle," says Sylvia Delvaille Jones of Villas & Apartments Abroad. "When we asked for the other angle, we gasped--there was another house not 50 feet away!"

14. How close are the nearest village and major road? Unless you plan a quiet retreat--catching up on sleep or relaxing by the pool--you'll want to be within easy access (three to six miles at the most) to a town or village, or at the very least a major road.

15. Does the villa have a modern kitchen...a great pool...beach access...dramatic views? Plan to cook wonderful meals using fresh produce? Then ask detailed questions about the kitchen. Prefer a glorious view to luxe decor? Make it clear. Jim Duggar of Villa Network has his clients prepare a "ten-point wish list" before they speak with him or an agent. "And I tell them they can probably expect to fulfill seven or eight of those wishes."

16. Does the villa have air conditioning? Most Italians and French--especially in the country--wouldn't dream of living with air conditioning. Rather, shutters are closed during the day to keep cool air in and opened at night to allow ventilation. Also, the windows at many Italian and French country properties don't have screens. Admits Scalzi: "At night, all the flora and fauna come in."

17. What's the quality of the bathrooms and bedding? In older European properties, "modern" plumbing can mean early 20th century or sparkling new. "We'll always tell clients whether the bathroom has a tub or a shower or whether the WC is separate," says Edward Marquis of International Chapters. "But we're more concerned, frankly, with the quality of the water pressure."

18. Do any animals reside on or near the property? This is especially important if you or anyone in your family suffers from an allergy to animal dander. Many European country villas are home to some sort of pet during a portion of the year or are regularly visited by neighboring cats and dogs.

19. Is there any nearby construction? It's an ongoing problem in the Caribbean, especially on St. Thomas, St. John, Barbados, Virgin Gorda, and St. Martin. Since construction may begin after you've booked, many companies have provisions in place to offer a refund, a discount, or relocation if feasible.

20. Do clients evaluate the property after their stay? The majority of rental companies follow up with questionnaires to their clients, often passing the reviews along to future clients. Ask to see them. Paul Mermelstein of Island Hideaways says they don't wait until a client returns: "We call after the first day to make sure everything is okay."

Life After Tuscany

For good reason, Tuscany, Provence, and the Cote d'Azur are popular with renters--so popular that they're routinely booked solid a year in advance and wildly congested from May to October. We asked agency executives to suggest alternatives--sleeper regions with that rare combination of ambiance, accessibility, and excellent villas.

The lush Dordogne river valley in southeastern France garnered enthusiasm for its picturesque rivers, medieval villages, and culinary excellence. "There are many Europeans there, but no Americans." "...And there's plenty of foie gras."

Northeast of Rome and southeast of Tuscany, Umbria has "beautifully decorated properties...in good proximity to small towns." "Better houses for far better prices [than in Tuscany]." One caveat: "Less hilly, less lush, and drier than Tuscany."

On the coast in the South of France near Spain, Languedoc was praised for its weather and affordability. "It has the feel of Provence, but with Mediterranean access." "It's also less crowded."

Marrakesh was highly recommended for its large, well-staffed villas. "There are fabulous homes and great people." "Morocco is a fascinating country."

Other European escapes: In Italy, Liguria, Abruzzo, and Veneto. In France, Midi-Pyrenees, Corsica, and St. Jean Cap-Ferrat. Up-and-comers included the Costa Brava north of Barcelona in Spain, and the Algarve coastline in Portugal. Caribbean possibilities: Virgin Gorda, Terre Bas on St. Martin, Anegada (a beach-and-lobster kind of place, population of 200, easily reached from Tortola), and Jamaica (the best value for fully staffed larger properties). The most far-flung recommendation: the Indian Ocean island of Mauritius, "a great add-on destination after a South African safari. The beaches are very Caribbean-like."