Run the numbers
Renting a villa is a terrific value proposition right now. Given the current economy, many second-home owners are offering their properties for the first time, and the increased supply means better deals. A large family can stay in a beautifully restored Tuscan farmhouse for less than the cost of an equivalent number of hotel rooms.
According to homeaway.com, which rents more than 185,000 accommodations online, 55 percent of all owners intend to give discounts and other perks this year, including free nights and relaxed minimum-stay requirements. You can get a sense of the market by doing a preliminary search on one of the multi-destination villa agencies’ Web sites.
Know What You Want Determine what kind of experience you’re after—particularly if you’re vacationing with a group. Do you require housekeeping every day, or are you willing to do your own dishes (even if there’s no dishwasher)? Would you prefer being more isolated, or within steps of town? If you’re considering extras—guided trips; an evening at the opera—confirm in advance your willingness to pay additional fees.
Get on the phone
Pictures on Web sites certainly help, but it’s always best to speak to an agent by telephone. (Some companies won’t even work with clients they haven’t vetted themselves.) Those we recommend here have firsthand knowledge of the properties and can answer questions you might not have thought of: How far away is the grocery store? Is emergency help nearby? Does the local host speak English? How new are the appliances? Many agents also have access to more rentals—either in a private portfolio or through other contacts—that they can offer once you’ve outlined your needs.
Take advantage of extras
Rental owners are staying competitive by offering such perks as free housekeeping, the use of a car, or a private chef. When inquiring about a property, it’s entirely permissible—and not at all uncouth—to ask an agent if the owner is willing to throw in anything else.
The best agencies leverage their industry contacts and relationships with property owners to organize things you couldn’t arrange yourself, be it a tasting in a noble family’s wine cellar or a hot-air balloon ride over the countryside. (Remember to confirm all related fees up front.)
Put it in writing
Signing a contract is standard when renting a villa. Like any agreement, this protects you, the owner, and the agent. Make sure it specifies which expenses are not included in the base price, such as taxes, air-conditioning, or the cost of heating the pool. A basic contract will also clearly outline policies regarding property damage, as well as what would constitute an unsatisfactory stay.
Consider buying insurance
Renting a villa is a large investment. Insurance can cover you in the event of a medical evacuation or an unforeseen conflict; it can also protect you from bad weather delays or errors made by the rental agency.
Some policies will let you cancel if you’ve recently been laid off from your job, while others will permit you to cancel for no reason at all. Expect to pay a premium of 5 to 11 percent of the trip’s prepaid, nonrefundable cost; cost may depend on the ages of the travelers in your group. Compare a broad range of policies on insuremytrip.com or use one of the five companies listed on tripinsurancestore.com.
Try an emerging destination
Travelers willing to move beyond blue-chip destinations can find incredible value in lesser-known regions. Carolyn Grote of Ville et Village recommends Île de Ré, an island off France’s west coast where more properties are becoming available. Other markets to consider are the Azores, Madeira, Malta, and the Italian regions of Puglia and Montepulciano. You’ll also find a growing number of attractive deals in Bosnia, Montenegro, and Slovenia.