Exclusive Tuscany
Est. MMXXV
Villa Sant'Anna, a villa in Castiglion del Bosco, Tuscany
19 photographs

Countryside Classic

Villa Sant'Anna

A 5-bedroom villa in Castiglion del Bosco, Tuscany

10 guests · 5 bed · 6 bath · private pool · from €101,500 / week

Represented by Exclusive Tuscany

10 guests · 5 bedrooms · 6 bathrooms

From €101,500 / weekAbout €1450 per person per night for 10

A personal reply from Smaranda within 24 hours. No obligation.

Keep this villa

At a glance: Villa Sant'Anna sleeps 10 in 5 bedrooms and 6 bathrooms in Castiglion del Bosco, near Montalcino in the Val d'Orcia. Pool: heated private pool, with a tennis court and pool house.

The essence

An enchanting five-bedroom stone villa, Villa Sant'Anna draws dawn-to-dusk light across exquisite Tuscan stonework, tranquil gardens and a private pool house. Sleeping ten across the main house and pool house, with a tennis court and a home-theatre room, it is a house for a family or group who want space, seclusion and the estate's pleasures close by.

The 3D tour

Walk through
the villa.

Move room to room in an interactive 3D model, or switch to the dollhouse view to see how the whole villa fits together.

The distinction

Why Villa Sant'Anna
is in the collection.

  1. 01

    Five en-suite bedrooms for ten, with a separate pool house and a home-theatre room.

  2. 02

    A private tennis court and a heated pool, set in tranquil gardens with an outdoor wood-fired oven.

  3. 03

    Countryside seclusion 2.8 km from the borgo, with the full service of the Rosewood estate.

The villa

Architecture & restoration

A living room with fireplace, a reading and home-theatre room, dining room and kitchen on the ground floor, with two en-suite bedrooms; the primary suite and two further en-suite rooms above; and a pool house with a living room and outdoor living area. WiFi, air conditioning and touchscreen controls throughout.

The setting

Land, view, context

Countryside 2.8 km from the borgo, amid tranquil gardens with open Val d'Orcia views.

Living here

Tennis at dawn, the pool and gardens through the day, a film in the home theatre, and dinner from the wood-fired oven — with the estate's winery, golf and Michelin-starred table close at hand.

Pricing

From €101,500 / week.

Weekly price calculated from seven nights at the starting nightly rate. Your dates, length of stay and any extras are confirmed in your quote.

Villa Sant'Anna is available to book through us directly. Tell us your dates and party, and we’ll reply within 24 hours with the exact rate and availability, with no obligation.

Ask about this villa

Ask about Villa Sant'Anna.

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Guests (sleeps 10)
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The estate

Part of Castiglion del Bosco.

See every villa at Castiglion del Bosco

One of thirteen private villas and suites on the five-thousand-acre Castiglion del Bosco estate, a Rosewood hotel in the UNESCO-listed Val d'Orcia near Montalcino. Houses can be taken together, and the medieval borgo — or the entire estate — reserved for exclusive use, with the resort's restaurants, spa, winery and golf club all on hand. A rare canvas for a wedding, a milestone celebration or a multi-family gathering.

Services

  • Daily breakfast delivered to the villa, and in-villa dining by the resort's kitchen
  • Daily housekeeping with evening turndown
  • A Land Rover Defender (or similar 4x4) with each villa for the length of the stay
  • A dedicated concierge and the full service of a Rosewood resort
  • Michelin-starred dining at Ristorante Campo del Drago, plus the Osteria La Canonica and the Lobby Bar
  • Rosewood spa and wellness centre, with treatments, fitness and pools

Experiences

  • Private tastings and vineyard tours at the estate's Brunello di Montalcino winery
  • Italy's only private golf club — an eighteen-hole championship course designed by Tom Weiskopf
  • Truffle hunting, cooking classes with the resort's chefs, and Brunello-paired dinners
  • La Festa della Domenica — a traditional Tuscan sagra in the borgo each summer Sunday
  • A private window over the Palio di Siena (2 July & 16 August) from the historic Palazzo d'Elci
  • Horse riding, e-biking and guided tours of Montalcino, Pienza, Montepulciano and Siena

Frequently asked

Questions about Villa Sant'Anna.

How many guests does Villa Sant'Anna sleep?
Villa Sant'Anna sleeps up to 10 guests in 5 bedrooms, with 6 bathrooms.
Does Villa Sant'Anna have a pool?
Yes: heated private pool, with a tennis court and pool house.
Where is Villa Sant'Anna?
Villa Sant'Anna is in Castiglion del Bosco, near Montalcino in the Val d'Orcia. See Castiglion del Bosco for the area.
Can a private chef be arranged at Villa Sant'Anna?
Yes. A private chef can be arranged at Villa Sant'Anna, for one dinner or for every evening of your stay.

Plan your stay around this villa.

Compare your options

Each collection shows guests, bedrooms and bathrooms side by side, so you can compare layouts at a glance.

Meals and gatherings

We can arrange a private chef for one dinner or every evening of your stay. Tell us the dates and guest numbers; menus and costs are quoted separately.

Golf during your stay

Rosewood villa guests have exclusive access to the estate’s private golf course; we book tee times in advance. Our Tuscany golf and villa guide covers the courses and the best villa bases for golf.

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