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2 Via del Lauro, Milano, 20121, Italy

With more than 500 listings, the Milan-based agency has a formidable presence in Greece, Italy, and Switzerland. Most villas have live-in managers to supervise staff and services. Dream & Charme doubles as a tour operator, so booking flights and rental cars is a seamless process.

Standout A restored Tuscan mansion, built in the 1400’s by the Medici family, is set on a hill covered in vineyards (six bedrooms; $20,000 a week).

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Dream & Charme

With more than 500 listings, the Milan-based agency has a formidable presence in Greece, Italy, and Switzerland. Most villas have live-in managers to supervise staff and services. Dream & Charme doubles as a tour operator, so booking flights and rental cars is a seamless process.

Standout A restored Tuscan mansion, built in the 1400’s by the Medici family, is set on a hill covered in vineyards (six bedrooms; $20,000 a week).