Steps for making your dream rental an affordable reality

Choose a destination where supply exceeds demand.
Pick places where villas are abundant: Forgo high-profile Anguilla for Virgin Gorda, overexposed Tuscany for Umbria. And consider the length of the rental season: Destinations where villas are filled three to five months of the year, such as Italy, are pricier than those where the season lasts eight or nine months, as it does in the Caribbean.

Go where the U.S. dollar is strong.
Greenbacks usually stretch a lot further in Costa Rica or New Zealand than in England or France.

Go where villas have adjustable rates.
In certain regions or seasons, if your group is not big enough to fill all of a villa's bedrooms, you can pay a fraction of the rate for a fraction of the bedrooms yet still have the property all to yourself. Even when adjustable rates aren't published, try to negotiate for them.

Prioritize your wish list.
Decide which features and amenities (a modern kitchen? air-conditioning? Wi-Fi?) you're willing to give (up to get those you can't live without. Say a beachfront location is a must: What can you (forgo in order to be able to afford it? On Barbados, for instance, oceanfront villas are not too expensive if you're willing to do without a pool. If what matters most is a panoramic ocean view, you'll save thousands of dollars by renting inland, atop a hill, and driving three minutes to the beach. Or choose (a house that's waterfront but requires a five-minute walk down a path to get to the beach. Ask your (villa rental agent which amenities drive up prices (the most at your destination, since these things vary from country to country. On the French Riviera, (for instance, air-conditioning, Wi-Fi, and a heated pool won't add much to the cost; in Tuscany, they'll send it soaring.

Consider what the rate includes.
Sometimes villa rental rates exclude a hefty tax, a cleaning fee, and additional charges for air-conditioning, heat, and the privilege of paying by credit card. Sometimes they include staff, beach-club (access, a rental car, and even a boat. If a villa does not have beach access, find out if you can buy day passes to a nearby oceanfront resort. Two years ago, my rate of $700 per night for a hilltop villa in Jamaica included day passes to a nearby beach resort with a water parkpasses that normally go for $55 per person.

Go where the cost of labor is low.
Having staff at your villa in the British or U.S. Virgin Islands, for example, is usually more expensive (than it would be on Jamaica or Barbados. Want (only a cook? Realize that at some destinations (e.g., Provence or St. Martin), "cooks are pricey gourmet chefs. You'll get better value if your cook is part of (a villa's built-in staff.

Consider renting a villa that's part of a set of residences which share certain amenities.
When you need fewer than four bedrooms and don't require the privacy of a freestanding house, this is an easy way to reduce your rental bill. Such villas often come with their own private pool and terrace for outdoor dining, yet they benefit from the shared staff and grounds. Use a rental agent who works directly with villa owners rather than with property management companies. Management companies tend to standardize the prices of all the properties they represent. Owners, however, may decide to price their villas below the current market value in order to rent them more often.