TuscanyVilla estate
Estate villas near Montalcino in the Val d’Orcia, with vineyards and countryside around them.
13 villas at Castiglion del Bosco in our collection, sleeping 4 to 12 guests; 11 have a private pool and 11 list a heated pool. The largest, Villa Agresto, sleeps 12. A private chef can be arranged at every villa.
13 villas in the collection
The estate
01 / 34
Watch
13 villas
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Castiglion 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.
Why Castiglion del Bosco
A villa here is not only a beautiful house. It comes with one of Italy's most private estates, run to Rosewood's standards of service, privacy and experience. Very few places in Europe offer that combination, and it is what you are paying for.
The villas sit inside a 5,000-acre estate in the Val d'Orcia. No neighbouring houses, no public roads, no crowds: miles of your own vineyards, woods and old paths from the front door.
Castiglion del Bosco is a working wine estate, with 62 hectares of Sangiovese vineyards producing its own Brunello. Tastings, vineyard picnics and dinners with the winemakers are part of the stay.
The Ferragamo family restored and built the estate, and it shows: in the care taken with the old buildings, in the design of the villas and in the standard of hospitality.
The estate is a favourite of families who value being left alone, because privacy is taken seriously here.
An eighteen-hole championship course reserved for members and resort guests: quiet fairways and tee times that are genuinely yours. A villa elsewhere cannot offer it.
The estate has its own heliport and transport service. From Florence, Rome, a private airfield, Sardinia or the Amalfi Coast, you can land on the estate and be at the villa within minutes.
Villa guests have their own guest experience team, and the planning starts before you arrive.
The estate's own idea of a household manager: one person who can be butler, local concierge, cook, housekeeper and help with the children. It feels like a private home, not a hotel.
A Michelin-starred restaurant, organic produce from the estate itself, and kitchens that will cook to almost any diet, with menus agreed before you arrive and served in the villa if you prefer.
More than fifty experiences, from truffle hunting in the estate's woods to vineyard picnics. On selected summer Sundays the medieval borgo hosts the Festa della Domenica: not a public festival, but an estate gathering of villa owners, guests and friends, with local food, wine, music and artisans.
Every villa comes with a seven-seat Defender for the whole stay, to explore the estate and the rest of Tuscany as you please.
The largest villa on the estate: exceptional privacy, a heated pool, a private tennis court, generous indoor and outdoor space for entertaining, and a pool house that can sleep extra guests. For a larger family or group who want the very best of the estate, this is the one.
See Villa OddiWhat the price reflects
The bottom line
These villas are not really competing with other Tuscan rentals. They compare with the finest fully staffed residences in St Tropez, Courchevel or the Caribbean, and against those, the price makes sense. You are not paying more for a bigger house; you are paying for one of the most private ways to live in Italy for a week.
On Castiglion del Bosco
Castiglion del Bosco is one of Tuscany's great private estates: five thousand acres of the Val d'Orcia, the UNESCO-listed valley south of Siena, gathered around an eight-hundred-year-old medieval borgo near Montalcino. Vineyards, oak woods and the bare clay hills that gave the world its idea of Tuscany run to the horizon; at the centre stand the restored hamlet, the ruins of an eleventh-century castle and the Romanesque church of San Michele. Brought back to life by the Ferragamo family and now a Rosewood hotel, the whole of it is farmed and run as a single hand.
It makes an exceptional base for the villas and suites we hold here, because a complete five-star resort is already on the land: a celebrated Brunello di Montalcino winery, Italy's only private golf course, a Rosewood spa, two restaurants and a constellation of experiences from truffle hunts to cookery classes. Each villa comes with a private pool, a Tuscan garden and its own seven-seat Land Rover Defender for roaming the estate, and the borgo, or the entire property, can be taken for exclusive use.
The heart of the estate is the borgo, a medieval village restored stone by stone, where forty-two of the resort's suites and three of its eleven villas sit among the lanes, a small piazza and the church of San Michele; the other eight villas are scattered across the surrounding countryside, each on its own patch of hillside. Around them lie the eleventh-century castle ruins, the Capanna vineyard, the Pieve San Michele archaeological site and a heliport, all within the estate's five thousand acres.
The setting is the Val d'Orcia itself, inscribed by UNESCO in 2004 for the landscape alone, with Montalcino on the western rise and Pienza, Montepulciano and Siena all within easy reach. It is some of the most cinematic country in Italy, and the estate sits in the middle of it with no near neighbour.
We represent thirteen of the estate's private homes: eleven villas of three to six bedrooms and two two-bedroom suites in the borgo. Each villa was designed by the Ferragamo family, and each comes with a heated private pool, a Tuscan-style garden and a seven-seat Land Rover Defender for the length of the stay. Some have particular character: Villa Biondi runs along the fairways of the golf course; Villa Castello is built on the medieval castle ruins, climbing three floors to a panoramic primary suite; Villa Oddi and Villa Sant'Anna each have a private tennis court. In the borgo, Casa Fontaccia and Casa del Vescovo are intimate suites for a couple or small family, with the village at the door.
Whichever villa you take, the resort's service comes with it, daily breakfast delivered to the villa, in-villa dining from the kitchens, housekeeping with evening turndown, and a dedicated concierge. Villas can be combined, and the borgo or the whole estate reserved exclusively, for a wedding or a gathering at scale.
Castiglion del Bosco is, first, a serious wine estate: its vineyards produce Brunello di Montalcino, one of Italy's most celebrated reds, and guests can take private tastings and vineyard tours, or join the ‘A Cena con Brunello' dinners that put the wine at the centre of the table. The Brunello is grown across the estate's own hillside parcels and aged in its cellars.
On the other side of the property is the only private golf club in Italy, an eighteen-hole championship course designed by Tom Weiskopf, laid through the oak woods and clay hills with long views over the Val d'Orcia. It is reserved for members and resort guests, which means quiet fairways and tee times that are genuinely your own.
Wellness is handled by the Rosewood spa and wellness centre, with treatments, fitness and pools set into the estate. The kitchens cover the rest: the Michelin-starred Ristorante Campo del Drago for refined Tuscan cooking, the Osteria La Canonica for trattoria classics and wood-fired dishes, and the Lobby Bar for an aperitivo by the fire. In summer the borgo hosts La Festa della Domenica, a traditional Tuscan sagra every Sunday, food, estate wines, live music and local artisans in the heart of the village, an easy, joyful evening for all ages.
Beyond the table, the experiences run deep: truffle hunting in the woods, hands-on cooking classes with the resort's chefs, e-biking and horse riding, and guided tours of Montalcino, Pienza, Montepulciano and Siena. Children are well looked after, and the seven-seat Defender means a family can set off together at a moment's notice.
For celebrations, the estate is a rare canvas. The castle ruins, the Bossi Garden, the Belvedere and the borgo itself stage weddings and dinners, and the property can be taken on a full buy-out, or the upper borgo reserved on its own, with the resort's event team planning around you. With ninety rooms across the suites and villas, the estate can host a large party in genuine comfort.
The calendar has its set pieces. Around the Palio di Siena, on 2 July and 16 August, the resort arranges a private window over the Piazza del Campo from the historic Palazzo d'Elci, a once-in-a-lifetime view of the race. And the estate stays open until Epiphany for its ‘Winter Magic' season: Thanksgiving, a Christmas of twinkling lights and fireside feasts, and a grand New Year's Eve, when the Tuscan landscape is at its quietest and most spellbinding.
When to come
May, June, September and into October are the loveliest windows, warm enough for the pools, with the vineyards in leaf or the harvest under way, and the Val d'Orcia at its greenest or most golden. High summer stays comfortable thanks to the estate pools and the spa, while the ‘Winter Magic' season, Thanksgiving through to Epiphany, brings fireside dinners, festive lights and an almost empty valley.
Towns worth knowing
Best for
If golf is part of your stay, our Tuscany golf guide explains the exclusive golf-course access available to Rosewood villa guests. Arrange tee times in advance, subject to availability.
Practicalities
Florence (FLR) is about ninety minutes by car and Rome Fiumicino (FCO) around two hours, often the easier flight for guests arriving from North America; the estate has its own heliport for private transfers. A car is useful for the wider valley, though most of a stay can happen on the estate itself. Each villa comes with a seven-seat Land Rover Defender, and full Rosewood resort service is included.
Frequently asked
Compare nearby areas and alternative bases
Planning the week