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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
Bedroom
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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Pristine and expertly designed, each Airbnb Luxe home comes with luxury amenities, services, and a dedicated trip designer.

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.
Amenities
Outdoor
Pool
Heated infinity pool
Tennis court
Dining area
Pizza oven
Kitchen
Pool house
Indoor
TV
Board games
Chef's kitchen
Indoor fireplace
Library
Minibar
Game room
Essentials
Wifi
Air conditioning
Washer
Outdoor seating
Shared
Sauna
Bocce ball court
Gym
Kids' club
Steam bath
Montalcino, Italy
Airport
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
Buonconvento
15 min(s) drive
Montalcino
24 min(s) drive
Siena
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.