U.S. & Canada
Beautiful Places: The Sonoma-based agency specializes in northern California’s wine country, with 35 handpicked properties that range from vineyard cottages to hilltop estates. It also has a robust portfolio in the Caribbean and Italy and a small collection in New York’s Hamptons.
Standout: Located between Napa and Sonoma, Villa nel Bosco has a working vineyard with Syrah grapes (four bedrooms; $9,400 a week).
Hawaii Hideaways: About half of the 250 properties on Maui, Kauai, Oahu, and the Big Island are located on the beach. A small but dedicated staff based in each destination can arrange activities that include private yacht charters and excursions with chefs to local farms.
Standout: Every room at the Sea Glass, in Kapalua, has a view of the mountains or the ocean (four bedrooms; $20,750 a week). 866/962-5642.
Tropical Villa Vacations: Most of the Maui-based company’s villas and homes—there are 43 in all—are within walking distance of the ocean. Owner Irene Anne Aroner personally draws up each day’s housekeeping schedule, while a former head concierge of the Four Seasons Maui at Wailea is always on call.
Standout: Azure Azul at Wailea Beach Villas has direct access to the resort’s two pools and eponymous beach (three bedrooms; $9,065 a week). 888/875-2818.
Entrée Destinations: This Vancouver-based operator has an outstanding portfolio of villas at British Columbia’s Whistler Resort that range from small châteaux to opulent ski chalets. Some properties have ski-in, ski-out access, while activities such as hikes with a helicopter drop-off can be arranged.
Standout: Massive cedar trees and fireplaces with log mantels give Whistler Private Home a secluded, mountain-home feel. Other amenities: a theater room and a spa with its own waterfall (four bedrooms; $28,400 a week). 888/999-6556.
Earth, Sea & Sky Vacations: Each of the 100 villas in Cabo comes with airport transfers, rental-car delivery to your door, and welcome cocktails. Hoping to book a restaurant reservation or a snorkeling excursion? Your local caretaker can arrange it all.
Standout: Villa Turquesa is on a cliff above Pedregal Beach and has a 730-square-foot infinity pool and a patio (nine bedrooms; $35,000 a week).
Journey Mexico: This collection of more than 700 Spanish-colonial mansions, traditional haciendas, and modern beachfront retreats is spread across Mexico, with the most offerings in the Riviera Maya, Puerto Vallarta, and Los Cabos.
Standout: Set within Tulum’s lush Sian Ka’an Biosphere Reserve, the light-filled Casa Nalum is within swimming distance of a pretty barrier reef (three bedrooms; $22,848 a week).
Villas by Linda Smith: Linda Smith stays in every property she considers for her collection, and she even designed two of the 90 villas in her portfolio. Each house is staffed with a chef, butler, housekeeper, and gardener.
Standout: Teak, Italian tile, and Persian rugs decorate Fortlands Point, overlooking Jamaica’s Discovery Bay, where coral reefs teem with parrot fish (seven bedrooms; $19,000 a week).
LaCure Villas: The global brand has 250 properties throughout the Caribbean islands, along with an extensive collection in Europe, South Africa, Costa Rica, Thailand, and Bali, Indonesia. Its concierge service can arrange for private chefs, nannies, and island tours.
Standout: Divine Villa Roaring Pavilion offers every service imaginable and is on a Jamaican beach featured in the 1962 James Bond film, Dr. No (five bedrooms; $33,600 a week). 800/387-2726.
McLaughlin Anderson: More than 100 listings run the gamut from cottages to estates, and are located in the U.S. Virgin Islands and the British Virgin Islands as well as Grenada.
Standout: 100 Pond Bay, on Virgin Gorda, in the British Virgin Islands, has three pools (five bedrooms; $7,000 a week).
St. Barth Properties: Owner and part-time St. Bart’s resident Peg Walsh and her staff regularly inspect the company’s 160 villas, which are located either on the beach or on the hillside.
Standout: Rent Steve Martin’s Villa Au Soleil, with a lily pond and a two-tiered infinity pool overlooking Baie de St. Jean (four bedrooms; $13,570 a week).