NORTH AMERICA

COSTA RICA

Playa Ocotal

Heather Mahaffey, Costa Rican Rentals, Alpharetta, Georgia
6 properties (low season, $2,800–$26,460; high season, $3,500–$29,260).
Overall portfolio: $$
Since Costa Rica is just entering the villa rental market, no agency has a large portfolio yet. At present, Mahaffey is the most knowledgeable, and any location in her nascent collection of all-inclusive villas is a great value. You pay based on the number of people, and the per-person per-night price includes a full-time maid, a cook, and all food and drink. Families enjoy the ease of staying in these properties and having Mahaffey arrange child-friendly day-trips and excursions. Playa Ocotal is far enough from major tourist areas that its beaches are nearly empty. But if you crave resort-style amenities, golf venues are within driving distance and spa treatments can be done at your villa (800-569-2688; reserve@costaricanrentals.com; costaricanrentals.com).

MEXICO

Los Cabos

Julie Schwab, Earth, Sea & Sky Vacations, Watsonville, California
104 properties (low season, $1,760–$36,000; high season, $2,275–$52,500).
Overall portfolio: $$
Schwab'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 Ping-Pong table or mariachi band in your villa? She'll make it happen (800-745-2226; julie@cabovillas.com; cabovillas.com).

UNITED STATES

California
Lorna Taylor, Beautiful Places, Sonoma, California
28 properties (low season, $1,750–$9,230; high season, $2,500–$13,000).
Overall portfolio: $$
Oenophiles will love Taylor'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 local vintners mean that she can arrange a lunch in a wine cave, a painting lesson in a vineyard, or a special tasting with a winemaker (800-495-9961; lorna@beautiful-places.com; beautiful-places.com).

Florida
William McClain, Villazzo, Miami
8 properties (low season, $12,600–$67,900; high season, $14,000-$83,300).
Overall portfolio: $$
These Miami-area rentals blend the best of two worlds, giving you the privacy of your own home along with the coddling of a top hotel. The stylish multimillion-dollar properties have been carefully selected and fitted with top-notch amenities (gourmet kitchens, wine refrigerators, Bulgari bath products) as well as a hospitality phone that provides one-touch access to room service and a 24/7 concierge. All properties come with daily housekeeping, and additional staff (such as a chef, a waiter, or a bartender) can be dispatched from the local office (877-845-5299; william.mcclain@villazzo.com; villazzo.com).