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Medieval farmhouse estate in Val d’Orcia foothills

9 guests · 5 bedrooms · 6.5 baths
Cypress dots the hills beyond the herringbone brick terrace at this rustic Tuscan villa. Tucked into the hillside on the grounds of 5-star Rosewood Castiglion del Bosco, there's loads to explore—a boutique vineyard, private golf course, bocce, and ancient ruins. A private heated pool, tennis court, and pizza oven all take in the views, and the nearest restaurants are within walking distance.
Sleeping arrangements
Ensuite bathroom, King bed, TV
Bedroom 2
Ensuite bathroom, King bed, TV
Bedroom 3
Ensuite bathroom, King bed, TV, Terrace
Bedroom 4
Ensuite bathroom, Single bed, TV
Bedroom 5
2 single beds, Ensuite bathroom, TV

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Villa Sant'Anna highlights
A heated pool
A pool house with its own lounge and kitchenette leads to the heated infinity pool, which reflects the area's wide open skies.
Vintage Tuscan grounds
Walking trails, a private golf course, and hills of ancient vineyards offer plenty of room to roam from this restored stone villa.
A restored interior with classic roots
Open-beam ceilings, antique furnishings, and wrought-iron 4-poster beds carefully maintain this villa's authentic Tuscan charm.
The Airbnb Luxe difference
Start-to-finish trip planning
Trip designers coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Airbnb Luxe home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any hour.
Heated infinity pool
Tennis court
Dining area
Pizza oven
Pool house
Board games
Chef's kitchen
Indoor fireplace
Game room
Air conditioning
Outdoor seating
Bocce ball court
Kids' club
Steam bath
Montalcino, Italy
Peretola Airport
103 min(s) drive
Pisa International Airport
138 min(s) drive
Leonardo da Vinci International Airport
169 min(s) drive
Points of Interest
15 min(s) drive
24 min(s) drive
53 min(s) drive
Have a question about this home?
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Pricing and availability
Cancellation Policy and House Rules
Cancel up to 95 days before your trip and get a full refund. Cancel within 95 days of the trip and the reservation is non-refundable.