Villas for 20 People in Italy: How to Find the Right One

Twenty people is a wonderful size for a villa trip: a milestone birthday, a family reunion, three generations in one place. It's also the size where the search gets hard. Villas that genuinely sleep twenty in comfort are a small share of what's available, and they're the first to go for summer.

One big house, or several on one estate?

A single villa with ten or more proper bedrooms exists, but not often. Many of the best options for twenty are estates: a main house with a separate farmhouse, cottage or converted barn on the same property, often sharing a pool and gardens. In Tuscany these are sometimes whole hamlets, known as borghi.

Estates have real advantages. Families get their own space and their own kitchen for breakfast, and everyone comes together for the pool and dinner. If your group wants to sleep under one roof, tell us early, because the choice is narrower.

Count bedrooms properly

• Separate adults from children. Twenty guests might mean eight couples and four children, or twelve adults who each want a room.
• Check the bed types. Twin rooms, bunk rooms and sofa beds are often counted as bedrooms. They suit children; they rarely suit couples.
• Count bathrooms. For a group this size, en-suite bathrooms matter as much as bedrooms.
• Think about who's where. Grandparents may want a ground-floor room; parents of young children want to be close to them.

The spaces that make a group trip work

• A table for everyone, indoors and outside. Dinner together is usually the point of the trip.
• A pool big enough for several people at once, with loungers and shade for the whole group.
• A kitchen that can feed twenty, or a cook. Cooking for this many every night isn't a holiday for anyone. See what a staffed villa includes.
• Places to be apart, too: a second sitting room, a quiet terrace, a garden bench with a view.

The best regions for twenty

• [Tuscany](/italy/tuscany): the widest choice of large estates and hamlets, especially around Chianti and the Val d'Orcia.
• Umbria: Tuscany's quieter neighbor, with spacious country estates.
• [Puglia](/italy/puglia): masserie, historic fortified farmhouses built around courtyards, many with room for large groups.
• [Sicily](/italy/sicily): large country villas and estates, particularly in the southeast.

Large villas are much scarcer on the Amalfi Coast and at Lake Como, where the terrain limits size. For those places, two neighboring villas can be the better answer.

Getting twenty people around

Plan transport early. Airport transfers for twenty usually mean a minibus or several cars. Once there, a few rental cars plus a driver for group dinners and day trips often works best. Check the villa's parking, and how far it is to the nearest village if not everyone wants to drive.

Booking and paying as a group

• Start early. For July and August, the best large villas are often reserved many months ahead.
• Nominate one organizer to deal with the villa and collect payments from the group.
• Read the rules on events, noise and extra guests, especially if you're celebrating.
• Understand the deposit and payment schedule before anyone commits.

Our villas for large groups page covers more of what to look for. Or simply tell us how your group is made up, and we'll search for villas that fit it.