NEW ZEALAND
Susie Marquis, The Villa Book, London
8 properties (low season, $3,850–$5,145; high season, $5,145–$6,370).
Overall portfolio: $
As a New Zealand native, Marquis knows the country as well as anyone can. She'll recommend that you take advantage of her properties' short three-night minimum and stay at two or three in different locations so that you can visit both the North and South islands. She'll also help you with car rentals so you can see the countryside in the best way possible (44-845-500-2000; susie@thevillabook.com; thevillabook.com).

WORLDWIDE

Maxine Harrison, Elysian Holidays, Tenterden, England
316 properties (low season, $825–$27,400; high season, $2,100–$70,450).
Overall portfolio: $$
The countries on Harrison's list nearly encircle the Mediterranean and dot the rest of the globe—South Africa, Thailand, and Tobago, to name a few. She's lived in many of the locations in which she represents homes, and her contacts allow her clients to experience the area's culture. All her properties are chosen for their regional character. Better yet, she knows which ones have owners and staff likely to invite their guests to celebrate local holidays with them (44-15-8076-6599; maxine@elysianholidays.co.uk; elysianholidays.co.uk).

Ian Holmes, Private World, London
120 properties (low season, $26,750–$427,750; high season, $40,100–$427,750).
Overall portfolio: $$$$
Holmes represents two jaw-dropping listings in each of 60 fashionable destinations around the world, from Anguilla to Zanzibar. Inhabited by their owners part of the year, his properties are all fully staffed and have a strong sense of style—especially his "rad pads" collection, featuring avant-garde design. The prices, like the homes themselves, may leave you breathless, but that's the cost of utter privacy and the world-class service Holmes provides (44-20-7723-5599; info@privateworldvillas.com; privateworldvillas.com).

Sylvia Delvaille Jones, Villas and Apartments Abroad, New York
300 properties (low season, $5,000–$300,000; high season, $7,000–$400,000).
Overall portfolio: $$$
Jones has Europe and the Caribbean well covered, with a select few properties scattered on four other continents. Her listings range from Caribbean beachfront cottages to a Tuscan estate that can sleep up to 100, with a focus on larger, high-end properties. She's especially attuned to multigenerational families' needs and will guide them to a child-safe house (complete with sturdy banisters) in a location with plenty of activities to keep all ages occupied. Her regional concierges can pull off just about any feat. She once arranged to have an opera staged at one of her Italian homes (212-213-6435; villas@vaanyc.com; vaanyc.com).