New Italian Villas for Rent

A sixteenth-century former convent, which is a better description than the one the estate usually gets. It sits between the Val di Chiana and the Val d’Orcia with sixty-five hectares of olive grove and garden around it, and seven suites that were each given their own character rather than a numbering system.

What the brochure copy tends to miss is the indoor half: alongside the 12-by-6 pool there is a gym, an indoor hydro-massage pool and a billiard room — which is what makes it work for a week that includes two days of weather. Pienza and the thermal springs of San Casciano dei Bagni are both short drives; Arezzo is under an hour, Florence an hour and a half.

Summer 2027 is published and Saturday-to-Saturday: $2,950 a night from 5 June to 16 July, $2,650 through 20 August, back to $2,950 until mid-September, seven nights minimum throughout. Rates ease to $1,650 outside the season.

Chianti Classico is the strip between Florence and Siena, and the villages everyone names — Greve, Castellina, Radda, Gaiole — are the ones on the main road. Trionfante sits in the quieter part of it, which in Chianti means fifteen minutes from all four and nothing at all outside the window.

The house is a good one for a group that wants to be together without being on top of each other: living room into a formal dining room with a fireplace, and upstairs a reading lounge that people actually use.

The Maremma is southern Tuscany, and it is emptier, hotter and closer to the sea than the Chianti postcard. Monte Mario is on the hills above Cinigiano with seven bedrooms and an infinity pool looking at all of it.

The commercially useful part: you can take four bedrooms rather than seven, with a five-night minimum, and arrive and leave on the days that suit you. Very few Tuscan estates of this size will do either, and for a party of eight it changes the arithmetic completely.

The largest of the four, and the one for a family that is really several families. Eighteen guests, two hectares of grounds outside Lucca, a pool and a private lake, and a set of themed gardens including a wedding garden with a wisteria gazebo — which tells you what a good number of its summers are for.

It also grows its own. Organic vegetables the villa chef cooks with, olives pressed for the house oil, a kiwi pergola, a lemon grove that becomes juice, candied fruit and limoncello. That is a rarer thing than a pool.

Most of Como’s famous houses are at the water and look across it. Molli is above Sala Comacina and looks down, which is the better view and the quieter commune — the lake’s only island sits in the middle of it, with the Costone ridge behind.

A modern house rather than a palazzo, with an infinity pool and hot tub on the balcony rather than at a boathouse, and five of the six bedrooms facing the water. Breakfast is laid every morning as part of the rate. Lido di Lenno is eight minutes down the hill, Menaggio nineteen, Bellagio forty-one, and Malpensa a little over an hour — which for a US arrival is the shortest transfer on this list. If you are still choosing a shore, our guide to the best places to visit on Lake Como covers the difference between them.

Ten bedrooms in a private park of palm and citrus at the centre of the San Giorgio Estate, with the Catania countryside opening out below. For a large group it is the easiest arrival on the island: wheels down at Catania and in the pool inside half an hour, which for anyone travelling with small children is the whole argument.

It is also on the right side of Etna for the wine estates, and within reach of both Taormina and the baroque south-east — the two Sicilies people usually have to choose between. More on that in our Taormina, Siracusa and Etna comparison.

The heel of Italy does something the north cannot: a house in the countryside that is seven minutes from sand. Petra sits above Fasano in six acres of olive grove, with thick whitewashed stone walls, vaulted ceilings, stone floors and arched entrances — architecture that was solving the Mediterranean heat four centuries before air conditioning. Six bedrooms, six bathrooms, and an annex studio with its own kitchenette.

An interior courtyard for gathering, two covered patios for eating outside, a pizza oven and an alfresco bar — with Alberobello’s trulli, the Grotte di Castellana and baroque Lecce all within a morning’s drive. Brindisi is under forty minutes. See the rest of the region on the Apulia collection — including Villa Stella (five bedrooms, from $2,013) and Angela (three bedrooms, from $1,006) if the party is smaller than Petra suits.