Tuscany, Italy

Rosewood Castiglion del Bosco Villa Sant’Anna

Price per night from$7,333.12

Price information

If you haven’t entered any dates, the rate shown is provided directly by the hotel and represents the cheapest double room (including tax) available in the next 60 days.

Prices have been converted from the hotel’s local currency (EUR6,804.77), via openexchangerates.org, using today’s exchange rate.


Sprawling Tuscan homestead


Vineyard-packed valleys





Poised between the vineyards and the golf club on Rosewood Castiglion del Bosco hotel’s verdant estate is Villa Sant’ Anna: a centuries-old (yet thoroughly modernised) Tuscan farmhouse. This five-bedroom, authentically renovated Italian casa stays true to its ancient heritage with exposed stone walls, beamed ceilings and polished, tiled floors. Modern touches bring the villa into the 21st century: whip up antipasti feasts in the spick-and-span kitchen; curl up with a classic film in the library; and wallow in the marble bath tubs big enough for two to soak in. On balmy days, knock a few balls around on the private tennis court before cooling off with a dip in the infinity pool; meanwhile, summer evenings will call for long, alfresco suppers on the terrace, with views of the Unesco-listed Val d’Orcia. 

Smith Extra

Get this when you book through us:

A wine-tasting tour for all villa guests

First Glance

  • The traditionally Tuscan Villa Sant’ Anna (655sq m) is spread over a two-storey, stone-walled farmhouse and a neighbouring pool house; modern fixtures and fittings include a private pool and a tennis court.
  • On the ground floor in the main house, there’s a high-ceilinged living room with exposed stone walls and a tiled floor. Patterned sofas and armchairs are grouped around a large fireplace; impressive Renaissance artwork hangs on the walls; and stone arches lead through to the staircase in the hallway.
  • Also on the ground floor is the library, which has a 40-inch LCD TV, bookcases lined with classic novels, and a selection of board games.
  • The ground floor kitchen is a bright, cosy space, with cherry-coloured cabinets, a pink-marble splashback and state-of-the-art appliances. These include a steel cooker and grill, matching pots and pans, a microwave, crockery and cutlery. The kitchen also has a washing machine and a Nespresso coffee-machine.
  • Double doors lead from the kitchen to the dining room, which has a long wooden table and tartan-covered chairs; large French windows let in plenty of light.
  • The ground floor also has a powder room.
  • In the next door pool house (all on one floor), there’s a spacious living room with a fireplace; the space is furnished with comfortable sofas and chairs in warm colours.
  • Also in the pool house, there’s a bathroom with a shower and Ferragamo bath products.
  • The Rosewood Castiglion del Bosco hotel is closed between 27 November and 12 April. Villas rented during this period will have a delivery of welcome groceries; two hours’ daily housekeeping; breakfast cooked in the villa (on request and for an extra charge); concierge service between 9am and 5pm; free newspaper app for Android and Apple devices; free WiFi and 24-hour security. Winter activities on the estate (at an additional cost) include wine tasting and tours of the winery, and access to the golf club.

Villa highlights

  • Private pool and tennis court
  • Large gardens
  • Furnished pool house

Sleeping arrangements

  • All of the five bedrooms are in the main house.
  • All the bedrooms (apart from the single room, which only has a shower) have an ensuite bathroom with a bath tub, a walk-in shower and Ferragamo bath products.
  • On the ground floor, there’s a double bedroom with a king-size bed dressed in luxurious linens; there’s also a walk-in wardrobe. French windows lead out into the garden.
  • Also on the ground floor is a single bedroom with an extra-wide single bed; this cosy room has large windows and is decorated in warm colours.
  • On the first floor is the master bedroom, which has a king-size four-poster bed; a walk-in wardrobe; and a red-and-white-checked footstool and chairs.
  • The double bedroom next door has a king-size bed, wooden furniture and views of the surrounding golf course and vineyards.
  • The twin bedroom (also on the first floor) has twin single beds with striped, white-cotton headboards, dressed in red-chintz linens. Two large windows make the room feel bright and airy.
  • Extra beds can be added on request; call the Smith24 Team for details.

Key kit

  • Flatscreen TVs in all bedrooms.
  • Free WiFi throughout.
  • Smartphone-enabled sound-system.
  • iPod dock.
  • Coal barbecue, on request.
  • Air-conditioning throughout.
  • Two hours of housekeeping and turndown service daily.
  • Welcome groceries on arrival.
  • In-villa breakfast service.
  • Access to the hotel's kids club.
  • Access to a free newspaper app for Android and Apple devices.
  • Access to the hotel's spa.


  • The 98sq m private infinity pool has views of the vineyards and golf course, and is surrounded by a stone seating area with sunloungers and rust-coloured parasols.


  • The enormous, lavender-scented gardens are comprised of a lawn; a terrace by the pool house (dotted with white-cotton-upholstered sofas and shaded by a wooden pergola); and a second terrace with a dining table and chairs outside the main house.
  • There’s also an alfresco dining area – with a round table and wrought-iron chairs – at the edge of the property, with panoramic views of the surrounding Tuscan countryside.
  • The villa has a private tennis court, and a working, wood-firing pizza oven.
  • There’s space for six cars in the private car park.


  • Villa Sant’ Anna is around two-and-a-half kilometres (a five-minute drive) from the little village of Borgo. The villa is perched on a ridge overlooking the hotel’s golf course and the Sangiovese vineyards.
  • Florence is the nearest international airport, a 90-minute drive from the villa. It’s well served by most airlines, including British Airways.
  • The historic heart of the estate, Borgo is dominated by the ruins of a medieval castle with the same name. Visit the church of San Michele Arcangelo; the historic manor house; the old winery and the stables.

The Guestbook

Whenever you book a stay at a Smith hotel or villa, we’ll invite you to review it when you get back. Read what other Smith members had to say in Rosewood Castiglion del Bosco Villa Sant’Anna’s Guestbook below.
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Price per night from $7,333.12

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