Historic Estate01
Villa San BartolomeoMontepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Spa · Infinity pool
The only villa in the Val d'Orcia with a private wellness centre of its own: an indoor pool heated to 38°C with hydromassage…
Luxury villas in the Val d'Orcia
Our Val d'Orcia villas sit in the landscape most people picture when they think of Tuscany: rolling clay hills, cypress avenues and hilltop towns, listed by UNESCO since 2004.
17 villas
Countryside Classic02
Villa AgrestoCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Spa · Heated pool
Six en-suite bedrooms for twelve, with a self-contained guest annex and kitchenette, room for a large family or group.
Historic Estate03
Villa Poggio d'OroMontalcino · 24 guests · 12 bedrooms
From €30,730 / week
Panoramic view
A 600 m² terrace raised above the countryside, with Montalcino straight ahead, the Val d'Orcia to the east and, on clear days…
Design Villa04
Podere MastrojanniMontalcino · 8 guests · 4 bedrooms
From €24,500 / week
Working vineyard · Pizza oven
Designed room by room by the artist Vittorio Corsini, every space one-of-a-kind, honest materials…
Countryside Classic05
Villa Casa del FiumeCastiglion del Bosco · 8 guests · 4 bedrooms
From €70,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Pizza oven
Four en-suite bedrooms for eight, including a pool house with its own living room and bedroom.
Wellness Estate06
Tenuta La BarricaiaVal d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Spa · Infinity pool
Thirteen en-suite bedrooms for up to twenty-six, eight in the main villa, five in a guest annex just metres away…
Countryside Classic07
Villa BiondiCastiglion del Bosco · 10 guests · 5 bedrooms
From €112,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Working vineyard
The estate's largest villa, 726 m², with five en-suite bedrooms for ten and a separate pool house.
Restored Borgo08
Casa del VescovoCastiglion del Bosco · 5 guests · 2 bedrooms
From €35,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A 200 m² two-bedroom suite in the heart of the borgo, in timeless Florentine style.
Countryside Classic09
Villa OlivieraCastiglion del Bosco · 6 guests · 3 bedrooms
From €77,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Three en-suite bedrooms for six, an intimate, refined house at the edge of the borgo.
Restored Borgo10
Casa FontacciaCastiglion del Bosco · 4 guests · 2 bedrooms
From €56,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
A detached two-bedroom suite in the heart of the borgo, with its own private entrance.
Countryside Classic11
Villa GauggioleCastiglion del Bosco · 8 guests · 4 bedrooms
From €98,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Gym
Four en-suite bedrooms for eight, three in the main house, one in a private guest annex with its own shaded pergola.
Countryside Classic12
Villa Sant'AnnaCastiglion del Bosco · 10 guests · 5 bedrooms
From €101,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Five en-suite bedrooms for ten, with a separate pool house and a home-theatre room.
Countryside Classic13
Villa StabbiCastiglion del Bosco · 11 guests · 6 bedrooms
From €108,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Panoramic view
Six en-suite bedrooms for eleven, across the main house, a guest annex and a pool house.
Historic Estate14
Villa CastelloCastiglion del Bosco · 6 guests · 3 bedrooms
From €84,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Built on medieval castle ruins, a three-storey house of real character, with a top-floor primary suite and panoramic views.
Countryside Classic15
Villa OddiCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Six en-suite bedrooms for twelve, across the main house and a pool house, generous space for a large group.
Countryside Classic16
Villa ChiusaCastiglion del Bosco · 8 guests · 4 bedrooms
From €94,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Four en-suite bedrooms for eight, including a private guest annex, and a separate pool house with a kitchenette.
Countryside Classic17
Villa AlbaCastiglion del Bosco · 6 guests · 3 bedrooms
From €63,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool
Three en-suite bedrooms for six, the most intimate of the estate's countryside villas, with a private guest annex.
Choosing the right villa
They cluster around Montalcino, on the Castiglion del Bosco estate, and near Montepulciano, with Pienza between the two. Florence airport is about 1 hour 45 minutes away, Rome Fiumicino about 2 hours 15 minutes.
Three ways to stay in the Val d'Orcia
An estate villa at Castiglion del Bosco. The Rosewood estate near Montalcino has private villas from two to six bedrooms, with its own vineyards and a private golf course for villa guests. See Castiglion del Bosco.
A large house for a group. Villa Poggio d'Oro near Montalcino sleeps 24 around a 600 m² terrace; Tenuta La Barricaia sleeps 26 in 13 en-suite bedrooms with a spa and infinity pool.
A villa with something no one else has. Villa San Bartolomeo near Montepulciano has its own wellness centre with an indoor pool; Podere Mastrojanni was designed room by room by the artist Vittorio Corsini, on a working vineyard in Montalcino.
Is the Val d'Orcia the right base?
Yes, if the landscape, Brunello and Vino Nobile, and quiet are the point of the trip. Pienza, Montalcino, Montepulciano and Bagno Vignoni are all within a short drive. Florence is about two hours each way, so plan one city day, not several; for more Florence, compare villas near Siena or Chianti.
Our Val d'Orcia guide covers the towns, wineries and the best weeks to come.
Frequently asked
- Where is the Val d'Orcia?
- In southern Tuscany, in the province of Siena, between Montalcino to the west and Montepulciano to the east, with Pienza in the middle. Siena is 40 to 60 minutes north.
- Which airport is best for a Val d'Orcia villa?
- Florence (FLR), about 1 hour 45 minutes to Pienza. From the US, Rome Fiumicino (FCO) is often better: about 2 hours 15 minutes by car, and it can save a connecting flight.
- Do your Val d'Orcia villas have private pools?
- Most do; each villa page states the pool exactly as it is. See also our [villas with private pools](/villas/private-pool).
- When is the best time to stay in the Val d'Orcia?
- May, June and the second half of September. The valley sits higher than Chianti, so spring arrives later and autumn earlier. Our [best time to visit Tuscany](/planning/best-time-to-visit-tuscany) guide has the detail.
See also
Tell us the dates, the numbers and what the week is for. , usually within a working day.