Siena Villa Rentals

Siena is the medieval rival of Florence that lost the rivalry and was preserved by it. The Republic of Siena fell in 1555 and was effectively frozen — no Renaissance rebuild, no baroque overlay, just a 14th-century city in red-and-pink brick.

The Campo is the most beautiful piazza in Europe — a shell-shaped slope flowing down to the Palazzo Pubblico, where the Palio horse race is run twice each summer (July 2 and August 16) and where most of Siena eats lunch the rest of the year. The Duomo is a Romanesque-Gothic black-and-white marble masterpiece, with the floor uncovered (twice a year) to reveal the Beccafumi and Pinturicchio inlays. The Torre del Mangia is the only secular tower in Italy taller than its city's cathedral.

Around Siena is the most beautiful Tuscan landscape — to the south, the Crete Senesi (the eroded clay hills with their tiny cypress-topped knolls and their sculpted ridgelines); to the southeast, the Val d'Orcia, the most photographed valley in Italy; to the north, Chianti Senese, the southern half of Chianti Classico. A villa in any of these is the trip.

The food in Siena is medieval-and-Tuscan: pici (hand-rolled noodles), pappardelle al cinghiale (wild-boar ragù), ribollita, pici cacio e pepe, panforte (the spiced fruit-and-nut cake, around since the 13th century), ricciarelli. Restaurants: La Taverna di San Giuseppe, Osteria Le Logge, Bar il Palio on the Campo for lunch, Antica Osteria da Divo, La Pasta Fresca.

May, June, and September are our favorite months. The Palio runs July 2 and August 16 — if you want to be in Siena for it, plan a year ahead. April is beautiful in the Crete Senesi (wildflowers). Late September and October are the vendemmia, beautiful and quiet.

Siena has the same inland Tuscan climate as Chianti — hot dry summers and cool damp winters. Monthly highs from around 49°F in January to 85°F in July and August. Pool weather mid-May through late September. The city itself stays cool in summer because of the stone and the hills.

The Palio runs twice each summer — July 2 (the Palio di Provenzano) and August 16 (the Palio dell'Assunta). If you want to be in Siena for it, plan well ahead — accommodation in the centro storico sells out a year in advance. The trial runs in the days before, and the contrada (district) dinners in the streets, are spectacular and almost as good.

Pici (hand-rolled noodles) with cacio e pepe or wild-boar ragù, pappardelle al cinghiale, ribollita, pici all'aglione, panforte, ricciarelli, cantucci with vin santo. Our favorites: La Taverna di San Giuseppe, Osteria Le Logge, Antica Osteria da Divo, Bar il Palio for lunch on the Campo.

A private Duomo and Piccolomini Library visit, the Campo at golden hour, the climb up the Torre del Mangia, the Pinacoteca Nazionale, a Brunello tasting at Montalcino, a Val d'Orcia driving day, a Crete Senesi morning at the Monte Oliveto Maggiore monastery, a cooking class with a Senese nonna.

The Val d'Orcia (45 min south), Montalcino and Montepulciano for the wines, San Gimignano and Volterra (90 min northwest), Florence (1 hr), Chianti (45 min), Cortona (1 hr east).

The centro storico is a limited traffic zone (ZTL) and entirely walkable. For day trips and for staying in the surrounding hills, a car is essential, or arrange driver service through our concierge.

Very few — the centro storico is mostly apartments and hotels, and it's a restricted traffic zone (ZTL). Almost all Siena vacation rentals are villas in the countryside within a 10–25 minute drive: the Crete Senesi to the south, Chianti Senese to the north, and the Val d'Arbia along the old Via Francigena. We think that's the better way to do it — city by evening, villa pool by afternoon.

Our hand-selected Siena villas start around €12,000 per week in high season for properties sleeping 10–12 guests, with larger estates from €25,000 and grand properties for 30+ guests priced on request. Weekly stays run Saturday to Saturday. Spring and fall rates are typically 20–30% lower than July and August.