1. Do Your Homework
Determine which amenities, like air-conditioning and Internet, are available and whether they're included in the price. And figure out what your living situation will be: Do housekeepers live on-site? Will you be sharing the pool or grounds with another couple? Also, look into how recent the website's photographs are, and ask if you can contact a past guest to use as a reference.
2. Book Early
Rentals can accommodate only one group at a time, so try to reserve 10 to 12 months in advance, says Lauren Bunton, senior travel advisor at Hosted Villas, an international luxury travel company based in Toronto.
3. Know What to Bring
Most spots include linens, basic toiletries, and household supplies, such as dishes and cookware, but you may need to pack items like converters, hair dryers, and bath goods, and plan on buying your own food. Bunton advises: "An agency should tell you exactly what's available up front."
4. Identify a Point Person On-Site
Make sure you get the name and phone number of a property manager or sales rep to call if a minor snafu arises while you're there.
5. Use Your Agency as a Concierge Service
The representatives should be able to give you detailed answers to questions about ground transportation, logistical issues, and activities. "When you've got limited time, you don't want to waste it searching for a decent grocery store or struggling with the details of how to rent a car -- that's what we're here for," says Bunton.