Tuscany, Italy

Rosewood Castiglion del Bosco Villa Oliviera

Price per night from$7,790.52

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 (EUR7,256.36), via openexchangerates.org, using today’s exchange rate.


Cool country casa


Timeless Tuscan estate





Originally home to an olive press on luxury hotel Rosewood Castiglion del Bosco’s sprawling estate, three-bedroom Villa Oliviera is aptly named. This Italian casa lives up to its centuries-old heritage in other ways, too: faithfully renovated rooms have beamed ceilings, polished-stone floors and wooden furnishings. A slick kitchen has everything you need to prepare a full Tuscan feast, and the master bedroom’s ensuite bathroom has a marble bath tub for two to soak in. You’ll be tempted outside not only by panoramic views of the Unesco-listed Val d’Orcia, but by the thought of lounging by the private infinity pool by day; and enjoying alfresco dinners on the pergola-shaded terrace by night. The villa’s also minutes from the little village of Borgo, where cobbled streets are lined with restaurants, a spa and a glass-walled fitness centre. 

Smith Extra

Get this when you book through us:

A wine-tasting tour for all villa guests

First Glance

  • This carefully restored, three-bedroom villa (418sq m) is set on a secluded spot of high ground overlooking Borgo; views from the terrace and pool provide glimpses of nearby Montalcino.
  • On the ground floor, there’s a living room with a beamed ceiling, a large fireplace and rustic wooden furniture. Floral-patterned armchairs and a white cotton sofa are grouped around the fire and the TV; polished wooden bookshelves hold stacks of novels. Two sets of double doors open onto the garden, letting in lots of natural light. There’s also a dining area with a large wooden table and chairs.
  • The traditional, ground-floor Tuscan kitchen has a range cooker (with a colourful tiled splashback), plum-coloured cabinets and a wooden table and chairs. High-quality cookware, cutlery and crockery are supplied. There’s also a microwave, dishwasher, sink, washing machine, kettle, grill and Nespresso coffee machine.
  • Next to the kitchen, there’s a laundry room and two powder rooms.
  • 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 infinity pool
  • Postcard-perfect views
  • Authentic Tuscan style

Sleeping arrangements

  • On the ground floor is the master bedroom, which has a king-size four-poster bed (dressed in white and orange linens); parquet floors; a walk-in wardrobe and traditional wooden furniture. The ensuite bathroom has a white marble bath tub; a walk-in shower and Ferragamo bath products.
  • On the first floor are two bedrooms. The first has a king-size bed and a walk-in wardrobe; large windows make this room light and airy. The ensuite bathroom has a bath tub, a walk-in shower and Ferragamo bath products.
  • The second room on the first floor has twin beds with red-and-blue-striped cotton headboards. There’s a walk-in wardrobe, and classic wooden furniture. The ensuite bathroom has a walk-in shower and Ferragamo bath products.
  • Extra beds can be added on request; call the Smith24 Team for details.

Key kit

  • Flatscreen TV in the living room and 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 50sq m heated infinity pool has views over the Val d’Orcia, and is surrounded by a stone seating area with sunloungers, chairs and sofas.


  • Next to the pool, there’s an alfresco dining area with chairs and a long table, shaded by a wooden pergola.
  • Padded, iron-framed sofas and chairs are grouped around a coffee table on the poolside terrace; a lawn leading from the house to the terrace has a table, chairs and a bright-yellow parasol.
  • There’s space for three cars in the private car park.


  • The villa is in the middle of the Rosewood Castiglion del Bosco estate, within walking distance from the hotel-owned village of Borgo.
  • Guests at Villa Oliviera have access to all the hotel’s facilities in Borgo, including the spa, two restaurants (La Canonica and Ristorante Campo del Drago), fitness centre and main infinity pool.
  • Florence is the nearest international airport, a 90-minute drive from the villa. It’s well served by most airlines, including British Airways.
  • Borgo is dominated by the ruins of a medieval castle with the same name. Visit 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 Oliviera’s Guestbook below.
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Price per night from $7,790.52