• USA: +1 917 336 4477
  • UK: +44 744 147 3289

Similar properties



Welcome to Villa Sant’Anna, one of most beautiful villa rentals in Tuscany. This elegant Tuscan country house is situated on a ridge overlooking the South-facing Sangiovese vineyards and the golf course at the Castiglion del Bosco estate. There are wonderful views from the house throughout the day.

This property is made up of a 5 bedroom main house and also a pool house. The main house has a very rustic look about it, it has a large living room with a traditional Tuscan fireplace, a reading room and a theatre room for sitting back and relaxing while watching a good movies.

The dining room area is open plan and has a separate country style kitchen. The house has air-conditioning throughout, also wireless Internet access and flat-screen TVs in the living room, reading room, bedrooms and pool house.

Villa Sant’Anna can accommodate up to nine guests in five bedrooms, all with en-suite facilities. There’s a master bedroom with king-size bed and en-suite bathroom and two further king-size ensuite double rooms. There’s a twin bedroom with two standard single beds and a single bedroom with an extra-wide single bed.

Outside there are several terraces and sun loungers for total rest and relaxation. If things get too hot, cool down in the swimming pool. Villa Saint’Anna has a outdoor wood oven for cooking traditional Italian style in the evenings. Imagine having your get-togethers with friends and family, sun setting in the background, homemade pizzas baking in the open-side oven and a nice glass of Montepulciano in your hand…. Sheer bliss !

The pool house which is just off the main building has a living room and open fireplace. There is also a bathroom and has a shady pergola for alfresco dining.

Bedroom 1 - Master
King size bed, En-suite bathroom, Flat screen TV

Bedroom 2
King bed, En-suite bathroom, Flat screen TV

Bedroom 3
2 Twin beds, En-suite bathroom, Flat screen TV

Bedroom 4
King size bed, En-suite bathroom, Walk-in closet, Flat screen TV, Terrace

Bedroom 5
Twin bed, En-suite bathroom, Flat screen TV
• Air conditioning
• Fireplace
• Satellite TV
• DVD player
• Video games
• Board games
• Wi-Fi access
• Library
• Mini bar
• Laundry facility
• Fully equipped kitchen
Outdoor Features
• Heated pool
• Pool house
• Outdoor furniture
• Alfresco dining
• Tennis court
• Heated infinity pool
• Steam bath
• Sauna
• Gym
• Bocce
• Access to Kids Club
• Note: Guests are asked to book the use of sauna and steam bath in advance to guarantee full and uninterrupted private enjoyment of these facilities.

Please note the following services included in the villa rates:

• Daily breakfast delivered in Villa
• Your Tuscan Dispensa - Welcome grocery upon arrival
• Newspaper application for Android and Apple devices
• Daily cleaning
• Check-out cleaning
• Private heated infinity outdoor pool
• Complimentary Wi-Fi in Villas and public areas
• Access to Kids Club and selected kids activities at the Resort
• Free use of sauna and steam bath at the Resort
• Fitness center, bocce and tennis courts at the Resort
• Gardener

Services that are provided and that can be included as an extra:

• Minibar
• Laundry service
• In-Villa spa treatments, private chef, meals and grocery delivery
• On-site Brunello di Montalcino winery
• Private 18-hole golf club
• La Canonica Cooking School, with organic kitchen garden
• The Spa at Rosewood Castiglion del Bosco
• Outdoor activities and excursions
• Valet service
• Private car transfer and rental services
• Private helipad and helicopter transfer service
• Tesla Destination Charging
• Events
• Babysitting
• Dog sitting
• Bodyguard

Location – distance to ( nearest airport/ major town/ bars/ restaurants)

• Montalcino (20 minutes)
• Historical, cultural and gastronomical tours of the Val d’ Orcia (max 1 hour)
• Day trip to Siena (35 min)
• Day trip to Florence (90 min)
• 120 km to Florence Airport
• 160 km to Pisa Airport
• 230 km to Rome Airport
• 43 km to private Siena Ampugnano Airport
• 67 km to private Grosseto Airport
• Villa Policies
• Children welcome
• Non-smoking villa
• Pets permitted
• Rental vehicle recommended

Area description

Perched on a ridge overlooking the Castiglion del Bosco golf course and Sangiovese vineyards, Villa Sant’Anna enjoys enchanting views from dawn to dusk. The home’s elegantly understated interiors are notable for their exquisite details, stonework and furnishings. The villa features a reading/home theater room as well as a private tennis court located within its extensive gardens. Rosewood Castiglion del Bosco is located in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia. It is set within a 5,000-acre, 800-year-old estate in Italy.


Strada Provinciale 103, 53024 Montalcino SI, Italy
Nearest airport Florence International Airport
Pisa Internarional Airport
Rome International Airport
190 km
180 km
220 km
Nearest restaurant Campo Del Drago 1 km


  • Bedroom(s): 5 ( Sleeps 9 )
    3 Double with en-suite, 1 Single with en-suite, 1 Twin with en-suite
  • Bathroom(s): 5
    3 Baths, 3 Showers, 6 Wash basins, 6 Toilets
  • General facilities: Ceiling Fans, Garden, Garden View, Gym - Communal, High Speed Internet, Panoramic Views, Parking, Pizza Oven, Safe, Terrace, Wifi
  • Indoor facilities: Air conditioning, Alarm Clock, All Bedrooms Air Conditioned, All Bedrooms En Suite, CD Player, Coffee Maker, Dishwasher, Drier, DVD Player, Freezer, iPOD Docking Station, Iron and Board, Microwave, Safe, TV
  • Outdoor facilities: Bbq, Golf field, Golf Views, Heated Pool, Parking, Restaurants nearby, Sun Loungers, Sun Umbrellas, Swimming pool, Tennis court
  • Services: Cleaning inclusive, Concierge Service, Daily maid service, Gardener, Kids club, Linen provided, Maid service, Towels provided
  • Access: Secure parking


Show Full Calendar Hide Calendar
It's Available!
Inquire now
  • Booked
  • Available
  • Pending


  • Concierge Service
  • Expert Advice
  • Personally Inspected Villas
- Nightly rate Weekly Min. Stay Change-over
Rate summary - - 1 Nights -

Request Rates

Additional Information

All prices are subject to tax at 10%

City tax of €3.50 per person per day for a maximum of 4 days.


Listing not yet reviewed by any guest.
Special Offers
  • Get in Touch

    Ask us about our special offers

    Contact Us
  • Join Our Mailing List

    Get offers sent direct to your mailbox

    Receive Offers

Expert Reviews

Listing has not been reviewed by our experts

Inquire About Villa

  • Name is required.
    An email address is required.
  • A valid phone number is required.
  • We need travel dates
    We need travel dates
  • Tick the box to submit the form.
Paul O'Sullivan

Our team know each destination and every villa we feature.

We also offer a personalized and fully complimentary concierge service so every part of your trip will be taken care of ensuring you have a hassle free vacation.

We look forward to hearing from you.

    • Type: Villa
    • Sleeps: 9
    • Bedroom(s): 5
    • Bathroom(s): 5
    • Board: Self Catering
    • Long term rentals: No
    • Pets: No
    • Children: Yes, great for kids
    • Wheelchair: No
    • Eldery or infirm: Yes
    • Holiday type: Family, Honeymoon, Rustic, Wedding Villas