Villa Sant Anna

Icon Map Marker Montalcino, Tuscany

Bedrooms 4Bedrooms
Guests 8Guests
Bathrooms 5 + 1 HalfBathrooms
Icon Size (Sf /Ft) 7,050SF

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Villa Sant Anna is a gorgeous traditional property located on the lush grounds of the Rosewood Castiglion del Bosco estate. This lovingly restored stone country manor dazzles amongst its majestic natural settings. Wondrous panoramas peer into the purest distillation of Tuscany's Val d'Orcia region, spanning rolling hills, endless vineyards, and world-renowned golf links.

Within Villa Sant Anna's rustic stone walls are timeless hallmarks of Tuscan country design, from beamed ceilings and terracotta floors to the spellbinding original fireplace of the living room. Old-world aristocratic elegance and plush contemporary furnishings merge harmoniously in the thoroughly dynamic and light-filled common spaces. Custard-toned walls and a palette of rich earth tones find expression through a wealth of timeless furnishings and textiles, curating an ambiance of eternal prestige and familiarity. Rounded French doors frame wondrous hill panoramas, ample light animating the interiors with an ethereal sun-kissed patina. Chiaroscuro painting adorns gorgeous internal stone arches grounding the vacation rental in proud renaissance heritage. Large French doors flood the dining room with light, while plaid upholstery doubles on country home romanticism. A charming provincial kitchen sets a picture-perfect environment for rediscovering classic Italian dishes, burgundy cabinetry, and tile backsplashes evoking the indulgent hues of local Chianti or Montalcino varieties. Villa Sant Anna offers four sumptuous en-suite bedrooms, accommodating 8 guests in utmost comfort, discretion, and style.

Romantic outdoor dining deck areas are splayed before outstanding panoramas of the Val D'Orcia, leaving nothing to be desired. Perfect the art of Italian country living with plenty of spots to enjoy a fine Chianti with loved ones. The spacious lot includes a heated pool and an autonomous pool house with a living room and kitchenette. A private tennis court adds to this Tuscan vacation rental's extensive recreation options.



  • Air Conditioning
  • Cable/Satellite TV
  • Dining Room
  • Fireplace
  • Laundry
  • Staff Quarters
  • Walk-In Closets
  • Wine Storage


  • BBQ
  • Lounger and Chair
  • Outdoor Dining
  • Outdoor Pizza Oven
  • Patio
  • Pool Outdoor Heated
  • Tennis Court
  • Terrace
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Every detail of your stay has been meticulously considered; each luxury home has a dedicated on-site team, including a steward, housekeeping staff, and field manager.

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Additional Services

To further elevate your stay, we offer additional services that include an on-site chef, pre-arranged chartered flights and yachts, access to exclusive establishments and events, and tailored experience packages.



Experts in the demanding fields of luxury home charters, service, and global luxury lifestyle and home management.


Confident in the quality of what we do and focused on the unique needs of an elite echelon of society.


Perceptive judges of conduct, tact and when to preserve appropriate silence preserving your privacy and safety.


Culturally discerning with refined elegant tastes that offers access to the world’s most rare elevated experiences.
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Enjoy Elite Privileges with LVH Membership

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Domus Application Form

Domus is an invitation-only membership granted only to a few individuals who will meet the requirements of our rigorous selection process. It will require a significant investment, but upon admission will grant the member access to a comprehensive lifestyle program and exclusive premium services that include a dedicated team available to you around the clock. Reach out to our Client Relations Manager to begin the process.


We pride ourselves in delivering exquisite home charters, tailored experiences, and premium home and lifestyle management to our clients anytime and anywhere. Let us be your family’s curator of immeasurable moments.
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Our community is our strength

Our exclusive community brings together a collective of trusted homeowners and guests who share a passion for refinement, elegance, and elevated human experiences. Become a member of our LVH family today, or for exclusive access to our ultra-premium services, upgrade your membership to Domus.
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Inquire About Villa Sant Anna | Tuscany

Thank you for your interest. We will make every effort to accommodate you in this home. If this property does not satisfy all your needs, know that there are comparable homes in the vicinity. Please fill up this form and our Client Relations Manager will guide you through the process.
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