How to Plan a Villa Vacation

How to Plan a Villa Vacation


1. Are you the villa type?

Renting a Caribbean villa can be “the best thing short of having a rich friend with a summer house,” says Smith, and most travelers will lap up the personal attention and privacy that villas afford. But if you’re the type who needs to be surrounded by crowds and in the center of all the action, you might want to think twice – or, as Smith suggests, book a villa either within a resort or with access privileges. “Most of our homes have complimentary membership at resorts nearby, so clients can enjoy the best of both worlds,” she says.

2. What do you need?

There are thousands of Caribbean villas, and identifying your needs is critical to narrowing the choices to a manageable handful. Must you be beachfront, or will a pool do? Do you need a full-time retinue, or can you get by with daily maid service? Do you want an active vacation packed with excursions or a fuss-free beach getaway? Will you need child care? On Smith's website,, a questionnaire helps customers refine their choices, and booking agents continue the process over the phone, asking an exhaustive list of questions that cover everything from allergies to favorite desserts. "The better the information we get, the better the service and the better the experience our clients will have," Smith says.

3. How big is too big?

You don’t need eight people to rent a private villa or home with four bedrooms. Many villas offer staggered rates, so depending on the size of the group, renters can pay either the one- to two-bedroom rate or a rate for three- to four- or five- to six-bedrooms and still enjoy all the amenities of a larger home. “You pay based on the number of bedrooms you need, not on the size of the villa,” Smith advises. So even if your group’s small, don’t limit your search to petite places; scope out a few larger homes too.

4. Who’s in your corner?

Particularly if you’re a first-timer, it’s smart to consult an agent. “The best have an intimate knowledge of not only the homes but also the destinations they represent,” says Smith. They’ll analyze your preferences, match you with the home that best meets your needs and be a valuable resource for local info – at no cost to you. Need a grand piano, kosher meals or gym equipment? An experienced agent can make it happen.

5. What’s the bottom line?

Be sure to verify exactly what the rental rate covers before you leave. “We tell our clients to budget for the three G’s: groceries, ground transportation and gratuities,” says Smith. Typically you’ll pay for airport transfers, food and drink, and additional services such as excursions, spa services and, in some cases, child care. Remember that gratuities are not optional: “We recommend 10 percent of the rental cost during high season and 15 percent in the summer,” says Smith. You can choose to prepay tips to your agent, who will distribute them to the staff, or use cash at the end of your stay.


1. Do you have personal knowledge of the villa?

You’re relying on an agent to be personally familiar with his properties, and staff members at the best agencies all should have visited the homes they represent at least once. Be wary if an agent can’t tell you with certainty how far away the beach is or whether bedroom two has garden or sea views. And don’t be afraid to inquire when someone from the agency last visited the villa. Wear and tear happens rapidly, and you want to be sure the home you’re renting looks the same as those pristine photos you saw online.

2. Can you put me in touch with former clients?

A reputable agent should be happy to connect you with former clients, so don’t be shy about asking for references. And when you do speak to past renters, make sure you ask the date of their visit; someone who stayed there five years ago may have had a very different experience from guests who just returned last month.

3. What if we have problems or questions while we’re there?

The whirlpool’s on the fritz, and you can’t figure out the security system. Who you gonna call? Hopefully your agency’s local representative, the concierge or the property manager. Before you jet off, ask for the contact number of someone on the ground who can sort out any snafus. When the air conditioning conks out on a 90-degree day, you’ll be glad you did.