Below is a roster of villa rental agents whom I consider best qualified to match Conde Nast Traveler readers with properties. To compile the list, I created a 53-question application designed to assess a rental 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 and other preparatory information and questionnaires that they give clients, checklists they use to evaluate properties, and at least one client reference. After carefully combing through these materials, we interviewed the most promising rental agents, by phone to evaluate their friendliness, honesty, and familiarity with the villas and regions they represent.
Only 48 agents made the cut. What separates the honorees from the also-rans? The best personally visted all of the villas they represent and slept in a good may of them. They inspect the properties at least annually. They speak the local language fluently. They handpick villas that have an authentic sense of place. And they themselves write or at least vet their house books, update them at least once a year, and fill 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 a single dollar sign($) for the least expensive to four ($$$$), indicating generally very expensive accommodations. Unless otherwise noted, prices relfect the cost of one-week rental. If you would like to nominate a villa rental agent for a future list or to comment on your experience with one of the agents listed below, please email me at email@example.com
Anne Pawsat, Hawaii Hideaways, Kula, Maui
115 properties (low season $7,350 – $54,500, high season, $8,000 – $72,000) overall portfolio $$$
Pawsat’s sumptuous oceanfront Hawaiian villas come with the latest and greatest amenities (granite counter tops, Bosch appliances) 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, who lives on Maui, combines intimate knowledge of the islands with (unusual in Hawaii) a type A efficiency born of a Yale education and years in the Northeast (808) 878-8559; firstname.lastname@example.org.
We had a wonderful time at Sail Away and I recommended Hawaii Hideaway to dozens of people. You were a delight to work with and I will definitely use you again the next time we rent a home in the islands.
Like a Dream
Bliss doesn’t even describe our experience. It was almost like a dream. We are ready to do this again with Hawaii Hideaways – you guys are the best. Everything was perfect!!!
Outstanding Experience From Beginning to End
It was in an outstanding experience from beginning to end, I would work with Hawaii hideaways again in the future unquestionably. Sunny Madeiros was terrific with her recommendations of everything from leisure activities to restaurants and even equipment rentals.
Coral Gables, FL
Perfect Combination of Elegance and Comfort
First time to Maui (and Hawaii). This is a spectacular setting and the home is a perfect combination of elegance and comfort. I could stay on the lanai all day long and be happy. Of course there’s a ton of fun activities, but it was great to have Gull Cottage as our base to come back to!
Arlington Heights, IL
You’re Going to Want to Stay
Our family spent a splendid week in Kauai in early 2017, basing ourselves out of the Touching Green house. It’s in a great location, has everything you need, and is just lovely. The pictures don’t do it justice. You’re going to want to stay!
New Rochelle, NY
A Treasured Memory For Life
We had a wonderful time in Kauai! We remained in awe at the unimaginable beauty, both of the rental home, as well as Kauai itself. It will be a treasured memory for life. I hope we can come back and make more memories.