MEXICO
Los Cabos
Julie Byrd, Earth, Sea & Sky Vacations, Watsonville, California
140 properties (low season, $1,890-$36,000; high season, $2,100-$52,500).
Overall portfolio: $$
Byrd's villas come with ocean views, a pool, and daily housekeeping, and the concierge team in her Los Cabos office is available around the clock. Want to charter a fishing boat, swim with dolphins, or have a mariachi band play at your villa? She'll make it happen (800-745-2226; (julie@cabovillas.com; cabovillas.com).

UNITED STATES
California
Peter Cheasley, (Luxury Retreats, Montreal
21 properties (low season, $2,765-$18,000; high season, $3,360-$18,000).
Overall portfolio: $$
Names once found within some of Cheasley's posh Palm Springs properties: Sinatra, Monroe. Names currently found in most of them: Sub-Zero, Frette. A three-night minimum makes these houses ideal for a long-weekend getaway, and if the hundreds of nearby golf courses are the main draw for you, Cheasley can offer knowledgeable recommendations on which courses to hit—and can schedule (the best tee times (877-993-0100, ext. 230; peter@luxuryretreats.com; luxuryretreats.com).

Liza Graves, BeautifulPlaces, Sonoma, California
30 properties (low season, $4,900-$35,000; high season, $6,125-$49,000).
Overall portfolio: $$
Oenophiles will love Graves's listings in California's wine country, which range from classic ranch homes to Tuscan-style villas; some properties even have vineyards. Her relationships with the local vintners mean that she can arrange for lunch in a wine cave, a painting lesson in a vineyard, or a special tasting with a winemaker (800-495-9961; liza@beautiful-places.com; beautiful-places.com).

Hawaii
Irene Ann Aroner, (Tropical Villa Vacations, Maui
45 properties (low season, $2,450-$59,500; high season, $2,450-$70,000).
Overall portfolio: $$$
Having spent more than a decade as a concierge at various Four Seasons hotels, Aroner brings an obsessive attention to detail to her property evaluations and customer service. She uses the most stringent criteria in selecting houses and performs regular inspections. As befits her background, Aroner offers extensive concierge services, such as arranging for a private dinner on the beach or yoga instruction (at your villa (888-875-2818, ext. 203; irene@tropicalvillavacations.com; tropicalvillavacations.com).

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; anne@hawaiihideaways.com; (hawaiihideaways.com).