1. Book through a reputable agency. The most essential quality in an agent is direct knowledge of the villas. The best ones have seen — or better, stayed in — the homes they represent. Look for someone who also knows the island well, who lives there or visit frequently and can give you the inside perspective on local customs, island life and how to make the most of your stay.
2. Plan to travel in the value season. This is from mid-April through mid-December. Rates can be as much as 40 percent off the rate in high season. And look for extras — like a rental car — that are included.
3. Don’t start with preconceived notions about a particular villa. Instead choose the three essential expectations you have for your villa experience so your agent can do the necessary research to provide the best options available.
4. For easier travel, look for islands with nonstop flights. Well-traveled spots like the Bahamas, Puerto Rico and St. Martin obviously fall into this category, but look for nonstops to places like Bonaire, St. Kitts and Trinidad too. Find a list of nonstop flights to unexpected Caribbean islands from an airport near you at islands.com/nonstopflights.
5. Check the list of amenities. You might assume certain comforts are included, but that’s often not the case. Air conditioning, for example, is not a given. A private pool is the most requested amenity, but again, not all villas have them.
6. Be upfront with your agent about your budget. He or she will help you get the best value for your dollar and factor in all the costs (groceries, taxes, tips) so there are no surprises.
7. Ask about lockouts. At many villas, you pay only for the bedrooms you use, so you may be able to rent a larger home at a lower price.
8. Know what staff is available. Household staff is one of the perks of a villa vacation. Available staff typically includes a housekeeper, chef, butler, laundress, gardener, wellness pro and a nanny. Tipping is a must, usually 10 to 15 percent. Ask your agent about paying in advance.