Val d'Orcia, Tuscany
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The Villa Sant'Anna, Val D’Orcia, Tuscany in southern Tuscany is equal parts estate and private resort. Guests will enjoy a remarkably beautiful setting, world-class amenities, and level of privacy and service difficult to find elsewhere. The villa is in the Sangiovese area of Tuscany, and is surrounded by many vineyards and wineries. The property enjoys panoramic views of the hills and landscape as well as an enormous, private garden of its own.

The property includes the main villa along with an elegant little pool house. Cross the stone patios surrounding the house and make your way across the lawn to the lovely pool and the equally charming pool house. A stone surround includes a covered terrace area where al fresco dining can be enjoyed, and you find a similar arrangement at the villa as well. Private tennis courts are nearby and a wood burning pizza oven is on hand for those who are eager to enjoy such a tasty dish.

Guests of the villa are welcome to use the spa and fitness center at the nearby estate as well, and a daily pastry delivery begins each day with a delicious treat.

Inside of the villa's buildings you will discover shared living spaces designed in the classic villa style. The stone walls, heavy beamed ceilings, terra cotta floors and large fireplaces show the loving hand used when renovating the property. There is a main hall, a library with generously sized seating, a warm and cozy dining room, and a country kitchen with modern appliances and casual seating. The pool house also has a living room with a working fireplace, a kitchen and a full bath.

The villa offers five bedrooms. Two of them are king suites with large beds, sitting areas and private baths. There is a single bedroom, a twin suite, and another king suite as well.

Sized for a relatively large gathering, the Villa Sant'Anna is ideal for a holiday in Tuscany or as the perfect base for several day trips into wine country.

The Weekly Rate Includes: Electricity, A/C, heating, water and final cleaning. Daily morning housekeeping service for two hours, daily turn down service, welcome Tuscan groceries upon arrival, newspaper app for Android and Apple devices, pastry basket delived daily,  free use of sauna and steam bath at Spa, private heated infinity pool, fitness center, bocce, and tennis courts upon reservation, kids club on the estate and kids activities, gardener and WiFi internet.

Food, beverage and provisioning fee not included.  Additional housekeeping, chef service, butler service, half board supplement, in villa dining service, additional bed, babysitting service, spa services, spa menu for in villa treatments and city tax are all at an additional cost and are paid locally in Euro or CC.  Please ask your villa specialist for quotes and charges.

Rosewood Castiglion del Bosco is a 5,000-acre country estate founded by Massimo and Chiara Ferragamo.
The 800-year-old estate comprises:
- A leading Brunello di Montalcino winery
- Two restaurants and two bars
- An organic kitchen garden
- A cooking school
- A mediaeval church
- A breathtaking 18-hole private golf course, designed by Tom Weiskopf
- A pampering spa and a fitness center
- A kids club

Note: Rates are subject to change prior notice. Please contact us for more information.


Bedroom 1: Ground floor bedroom with a four-poster king-size bed, sitting area, private terrace and en-suite bathroom with bathtub, shower, double vanity and WC.

Bedroom 2: Ground floor bedroom with a single bed and en-suite bathroom with shower, vanity and WC.

Bedroom 3: First floor master bedroom with a four-poster king-size bed, sitting area, walk-in closet and en-suite bathroom with bathtub, shower, double vanity, WC.

Bedroom 4: First floor bedroom with a four-poster king-size bed, sitting area and en-suite bathroom with bathtub, shower, double vanity, WC.

Bedroom 5: First floor bedroom with two single beds and en-suite bathroom with bathtub, shower, vanity and WC.

All bedrooms have A/C and flat screen TV.


  • Air Conditioning - Bedrooms
  • Alfresco Dining Area
  • Assigned Parking
  • Bed and Bath Linens
  • Bocce Ball Court
  • Children Welcome
  • Daily Turndown Service
  • Dishwasher
  • Dryer
  • DVD Player
  • Fireplace
  • Fitness Room - Community Shared
  • Golf (Nearby)
  • Gourmet Kitchen
  • Heating
  • Interior Bedrooms
  • iPod Dock
  • Library
  • On-Site Heliport
  • Phone
  • Pizza Oven
  • Resort Privileges
  • Restaurant
  • Security System
  • Spa
  • Tennis Court(s)
  • TV - in each Bedroom
  • TV - Satellite
  • Washer
  • Welcome Provisioning
  • WiFi
  • Gardener
  • Housekeeper(s)
  • Pool Person
  • Property Manager on Call
  • Outdoor
  • Private
  • Damage Deposit: Upon Arrival - Credit Card Authorization in case of damages.
  • Children Welcome (all ages)
  • Pets allowed with permission
  • No Smoking
  • Housekeeping: Maid service 7 days a week
  • All extra charges to be paid at end of stay in local currency.
  • Breakfast included
  • Kids Club
  • Provisions and groceries are not included
  • Rates set in Euros. Prices in other currencies my fluctuate.
  • Utilities included
  • Villa orientation
  • Deposit/Payment: 50% at the reservation. Balance due 30 days prior to arrival.
  • Check In / Check Out: 4 pm / 10 am
2018 Jun 1 to Oct 1 June 1, 2018 - October 1, 2018 (7 night minimum) 5 $10,844.40 $75,910.80
2018 Oct 1 to Nov 1 October 1, 2018 - November 1, 2018 (7 night minimum) 5 $9,194.40 $64,360.80
2018 Nov 1 to Nov 18 November 1, 2018 - November 18, 2018 (7 night minimum) 5 $6,686.40 $46,804.80
2018 Jun 1 to Oct 1 June 1, 2018 - October 1, 2018 (7 night minimum)
Bedrooms: 5
Daily: $10,844.40
Weekly: $75,910.80
2018 Oct 1 to Nov 1 October 1, 2018 - November 1, 2018 (7 night minimum)
Bedrooms: 5
Daily: $9,194.40
Weekly: $64,360.80
2018 Nov 1 to Nov 18 November 1, 2018 - November 18, 2018 (7 night minimum)
Bedrooms: 5
Daily: $6,686.40
Weekly: $46,804.80

Note: The rates above are subject to 10% Tax/Service Charge.
Payments accepted in US Dollars, Euros, British Pound, Canadian Dollars, Swiss Franc, Fijian Dollars, Thai Baht, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.

Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.
STARTING AT $6,686.40/Nt
Please try again or contact us for possible waiver at 1.704.256.8327 or [email protected]
Your Estimate:
(Estimate does not include applicable promotions.)


Due to villa's privacy policy, the nearest town is presented on the map




"Villa was better than advertised. Great indoor and outdoor space with comfortable furniture and bedrooms. Some members of our party would have liked curtains (window coverings) in the bathrooms, but not a big issue due to the privacy. Your services from initial contact on website through to greeting at Villa and maid service were excellent. "
Nick S.
La Pinta