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Villa Sant’Anna

5 Bedrooms — 9 Guests

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A beautiful villa with the most incredible views of Val d’Orcia

Elevated on a ridge overlooking a golf cllub and the Brunello di Montalcino’s vineyards to the south, Villa Sant’Anna offers spectacular views from sunrise to sunset.

It is a warm and stylish villa set amongst vast landscaped grounds. The property features a heated swimming pool and a tennis court to keep guests entertained. A convenient pool house contains a shower room, kitchenette and living room.

In the main villa, guests can relax in the spacious living room with its comfortable sofas surrounding the authentic Tuscan fireplace, or enjoy a film in the home theatre and library room. There is an elegant dining room for enjoying feasts cooked up in the fully-equipped, country-style kitchen.

Ideal for groups of different compositions, there are three double bedrooms, one twin and one single, all with en-suite facilities.

Villa Sant’Anna is the largest of 11 villas in the 5000-acre Rosewood Castiglion del Bosco estate. The estate offers two restaurants, a cooking school, a fitness and spa complex, tennis courts, a private golf course, and a chapel, all surrounded by 70 hectares of vineyards.

Highlights

Landscaped Gardens

Landscaped Gardens

Outdoor Living & Dining

Outdoor Living & Dining

Heated Swimming Pool

Heated Swimming Pool

Services

Included

Available extras

Enhance Your Stay with Personalised Services

After booking, your dedicated concierge will craft the perfect experience — tailored to your preferences. From everyday essentials to exclusive experiences, our curated add-ons elevate every villa stay.

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Essential

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Signature

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Prestige

Features

Indoor

Outdoor

Bedrooms

This property comfortably accommodates up to 9 guests in its 5 bedrooms.

GROUND FLOOR
Bedroom 1 – king-size bed, and en-suite bathroom with bathtub & separate shower
Bedroom 2 – single bed (extra-wide), and en-suite bathroom with shower

FIRST FLOOR
Bedroom 3 (Master) – king-size bed, sitting area, walk-in wardrobe, and en-suite bathroom with bathtub & separate shower
Bedroom 4 – king-size bed and en-suite bathroom with bathtub & separate shower
Bedroom 5 – twin bed (2 x single beds), and en-suite bathroom with bathtub & separate shower

Location

Disclaimer: the location on the map may be approximate due to privacy reasons.

About the area

Villa Sant’Anna is located within the Castiglion del Bosco estate in the Val d’Orcia region of Tuscany.

Located on the ancient Via Francigena – a route once travelled by merchants and pilgrims, the estate is home to an abundance of wildlife in its dense woodlands.

The UNESCO World Heritage Site of Val d’Orcia is characterised by rolling hills, sweeping vineyards, and picturesque towns and villages such as Pienza, Radicofani and Montalcino.

Distances

Frequently asked questions

Inclusions vary by property but generally cover accommodation, cleaning services, and basic utilities. Some villas may also include additional services such as concierge, breakfast, or a private chef. Full details can be found on each villa’s page. If a service is not included in the price, our concierge team can arrange it for you, ensuring a fully personalized stay. Let us know your preferences, and we’ll take care of the rest!
Booking is simple! If you have a specific villa in mind, click "Send Enquiry" on its page. If you're considering multiple options, click the heart icon to save your favorites and send one enquiry for all of them. Our team will check availability and send you a detailed offer within 24 hours. Need help choosing? We’re happy to assist!
Yes, a deposit is required at the time of booking, typically 30% of the total amount. The remaining balance is usually due 30 to 90 days before check-in, depending on the property. Some villas may have different payment schedules, which will be specified in the offer we send you.
We accept bank transfers and major credit cards. Payment details will be provided during the booking process.
Yes, we offer a wide range of services, including in-villa options like private chefs, chauffeurs, and spa treatments, as well as activities such as yacht charters, wine tastings, and guided tours. We can also arrange experiences for the rest of your holiday, even beyond your villa stay. After booking, your dedicated concierge will contact you to customize your itinerary.
Yes, most high-end villas require a minimum stay of 7 nights, usually starting from a Saturday. However, many properties offer flexibility during certain times of the year, except for peak seasons like summer and Christmas holidays, which typically have stricter requirements. A smaller number of properties accept shorter stays year-round. If you have specific dates in mind, please contact us for availability.
Yes, we offer commission to travel agents booking on behalf of their clients. The commission amount varies by property, please contact us for specific details regarding a particular villa.

Have more questions?

Connect with our Villa Experts – we’ll handle the rest.

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Villa Sant’Anna

Villa Sant’Anna

When?

Minimum stay for most villas: 7 nights, Saturday to Saturday.

What works for you?

Prices available on request.

Final price to be confirmed by our customer service team.

Add dates to view exact price.

From 44.275,00 EUR per week, to price on request

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  1. Travel info
  2. Contact details
  3. Confirmation

Arrival and departure dates

When?

Minimum stay for most villas: 7 nights, Saturday to Saturday.

What works for you?

-

Guests and bedrooms

Minimum bedrooms

Adults (ages 13 or above)

Children (ages 2 - 12)

Infants (under 2)

Pets

Price range per week

Helps us offer you the most relevant villa options.

0 EUR 1 000 000 EUR

Contact details

    Thank You!

    We've received your enquiry! Our Villa Expert will be in touch shortly, and your full offer will be ready within 24 hours.

    Price rates

    Price per week. Price for shorter stays available on request; minimum stay 4 nights. Alternative options available to accommodate additional guests equally luxuriously.

    From 44.275,00 EUR per week, to price on request

    Superb Service

    5/5

    "Thank you My Private Villas for the outstanding service. Paolo Macchiaroli goes above and beyond to accommodate all our needs, making for an exquisite vacation."

    — Sir Anthony Hopkins

    Why guests love our villas...

    Wonderful vacation in an island paradise

    5/5

    "Excellent and very responsive service. They coordinated all aspects of our stay very efficiently. A great team to work with."

    — Lynette

    Top villa rental company

    5/5

    "Best villa rental company we have ever used. We found them to be easy to communicate with, expert, friendly and cooperative, to assure that our stay was enjoyable."

    — Jim Long

    Amazing

    5/5

    "Service was very excellent. Owners were very helpful and caring."

    — Trusted Client

    Servizio impeccabile, ci hanno organizzato la vacanza in ogni dettaglio.

    5/5

    "Cura del cliente ai massimi livelli. Assistenza h24, profonda conoscenza della proprietá e della destinazione. Hanno reso la vacanza indimenticabile. Saro’ sicuramente loro cliente a vita, assolutamente migliori di qualsiasi altro operatore di cui ho usufruito."

    — Francesco

    Wonderful to work with!

    5/5

    "Best company to schedule a vacation with! My family and friends were celebrating my 50th birthday in the south of France. My Private Villas helped me with the villa selection (it was stunning!), the chef and dinner party at the house. It was all fabulous! Couldn't have asked for a better celebration. We will definitely be using them again...possibly when our daughter graduates college in a few years!"

    — Cristina March

    First class operation!

    5/5

    "The attention to detail and ease of booking process was excellent. The customer support was 1st class. The on-site team at the villa was superb, and arranged anything we needed."

    — Trusted Client

    Best holiday ever!

    5/5

    "The house was outstanding and exactly as described. Furthermore Francesca provided a very friendly, proactive and highly efficient follow-up on all the details we requested to make this our best family holiday ever."

    — Simon Coombe

    Wonderful villa in spectacular surroundings!

    5/5

    "A very thorough approach to the process of advising on numerous points of detail raised by a 10 strong party whose ages ranged from 7 ti 69. Clear understanding of the facilities and services on offer and how they could be tailored to accommodate us all. Communications were clear and questions addressed promptly. Issue on arrival was dealt with promptly and to our satisfaction."

    — Dennis

    10/10 Company!

    5/5

    "Great service! They helped us throughout the whole process, even though it was very last minute. Francesca is wonderful, looking forward to working with her again: she made the whole experience 10 times better."

    — Trusted Client

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    Villa Sant’Anna

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    Villa Sant’Anna

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