Luxury villa destinations across Europe, the Caribbean and beyond

Not every villa suits every kind of trip, so it helps to start with who’s going.

• Families of 5–8 — flexible bedroom layouts or a separate guest annexe for grandparents or teens, trips built around July–August school-holiday windows, and a pool and garden the group can use without leaving the property. Families are the largest single group booking with us.
• Couples and milestone trips — honeymoons, anniversaries and significant birthdays for 1–4 guests. This cohort skews the most premium of any group booking, and privacy matters more than square footage.
• Large groups and retreats of 9+ — reunions, weddings and corporate offsites, planning furthest out (median lead time around five months), usually starting as a custom quote rather than a straight villa pick.

Italy is one of the three deepest markets and works best for families and larger groups. Tuscany carries the most properties — Lucca near its walled old town, Siena in wine country, Cortona with views over the Val di Chiana, San Casciano dei Bagni for its thermal springs. Puglia is flatter and closer to the sea, with Ostuni’s white old town, Savelletri near Fasano and the cliffs of Polignano a Mare, usually chosen for beach access alongside trulli and masseria architecture. Sicily, Capri and Umbria round it out.

For a ski week or a snow-season base, the collection reaches into the Alps. In Switzerland, Verbier is home to The Lodge, a dual-season chalet that also takes summer room bookings, and Crans-Montana adds a sunnier, family-friendly plateau. Austria covers Kitzbühel, Lech and Westendorf for classic Alpine skiing, and on the French side Courchevel and Megève pair the slopes with the Alps’ best tables. Most alpine chalets work in summer too, for hiking and cooler mountain weeks.