Back deck looking over the grass and ocean at Sweet Escape villa rentalBack deck looking over the grass and ocean at Sweet Escape villa rentalBack deck looking over the grass and ocean at Sweet Escape villa rental

Hawaii Hideaways
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Condé Nast Traveler

Wendy’s Rolodex – Worldwide Villa Rental Guide – Your Indispensable Guide to 49 Rigorously Vetted Villa Rental Agents

June 2009

Below is a roster of the villa rental agents whom we consider best qualified to match Conde Nat Traveler readers with properties. To compile the list, we created a 47-question application designed to assess an agent’s competency, connections, and business practices. We asked each agent to send a sample house book (that invaluable guide to a villa and its environs), sample driving directions, as well as other preparatory information and questionnaires that they give clients, check-lists that they use to evaluate properties, and at least one client reference. After carefully combing through these materials, we interviewed teh most promising rental agents by phone to evaluate their user-friendliness, honesty, and familiarity with the villas and regions they represent.

Only 49 agents made the cut. What separates the honorees from the also-rans? The best have personally visited all of the villas that they represent and have slept in a good many of them. They reinspect properties at least annually. They speak the local language fluently. The handpick villas that they have an authentic sense of place. And they themselves write or at least vet their house books, updating them once a year at minimum and filling them with insider tips. Some agents have a preponderance of modest cottages, others fairy-tale estates, and we’ve characterized their overall portfolios accordingly-from one dollar sign ($) for the least expensive to four ($$$$) for very expensive accommodations relative to their regions. Unless otherwise noted, prices reflect the cost of a one-week rental. If you would like to nominate a villa rental agent for a future list or to comment on your experience with one of the agents below, please e-mail me at

Anne Pawsat-Dressler
Hawaii Hideaways, Maui
150 properties (low season, $7,350-$54,500 high season, $8,000-$72,000). Overall portfolio:$$$ Pawsat-Dressler’s sumptuous beachfront Hawaiian villas come with the latest and greatest amenities (Bosch appliances, HDTV, iPod docks) and a 24-hour concierge who can line up everything from a private heli-hiking tour of Molokai to a pedicurist who makes house calls. Pawsat-Dressler, who lives on Maui, combines intimate knowledge of the islands with a type-A efficiency born of a Yale education and years spent in the Northeast (808-878-8559;;

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