Villa Cypresso San Casciano: Historic 6-Bedroom Tuscan Estate with Private Pool in the Heart of Chianti Wine Country

This luxury villa rental in Chianti Tuscany offers an extraordinary escape in a meticulously restored 17th-century farmhouse, where ancient stone walls and terracotta floors tell stories of centuries past. Set on 30 hectares of rolling vineyards and olive groves in San Casciano Val di Pesa, this remarkable estate combines authentic Tuscan heritage with contemporary comfort for up to 12 guests.

The Villa

The 350-square-meter villa unfolds across two levels, showcasing the masterful restoration of this protected historical property. Original features include soaring beamed ceilings, traditional terracotta floors, and two magnificent open-hearth fireplaces that anchor the living spaces. The ground floor flows seamlessly between multiple living areas, including a formal dining room that opens to the garden loggia and a spacious kitchen equipped with five-burner hob, dishwasher, and modern appliances. An antique wood-burning oven serves as a striking decorative centerpiece, honoring the villa’s culinary heritage.

Six generously appointed bedrooms include four double rooms and two twin rooms, each thoughtfully designed with authentic furnishings and equipped with private bathrooms featuring both baths and showers. The master suite opens directly to a private terrace overlooking the vineyards, while upper-floor bedrooms provide panoramic countryside views through original windows.

Outdoor Living

The villa’s 2,000-square-meter private garden creates multiple outdoor living experiences, from the Roman-stepped swimming pool to intimate terraced dining areas. The 70-square-meter pool, available from April through October, features an outdoor shower and is surrounded by manicured lawns dotted with fragrant Mediterranean plants. Three distinct terraces offer different perspectives of the surrounding landscape, including a covered loggia with dining table and a panoramic terrace featuring a striking glass and stone table.

A furnished gazebo with large iron table accommodates al fresco dining, while the barbecue area and multiple outdoor seating spaces provide perfect settings for evening gatherings. The property’s elevated position ensures cooling breezes and spectacular sunset views across the Chianti hills.

Exploring San Casciano Val di Pesa and the Local Area

The villa’s location in San Casciano Val di Pesa places guests at the heart of Chianti Classico wine country, with the charming town center just 4 kilometers away. This historic comune offers authentic Tuscan experiences, from weekly markets to traditional osterias serving regional specialties. The villa provides unique opportunities for wine tasting sessions featuring estate-produced Chianti Classico, Vinsanto, and olive oil.

Florence lies just 22 kilometers north, easily accessible for day trips to world-class museums and Renaissance architecture. Siena, the medieval jewel of southern Tuscany, awaits 55 kilometers south. For detailed information about local attractions and activities, visit the official Tuscan tourism website. The villa serves as an ideal base for exploring celebrated wine estates, hilltop villages like Greve in Chianti, and the scenic Via Chiantigiana wine route.

Families and Groups

The villa excels as a multi-generational retreat, offering ample space for privacy and togetherness. Six full bathrooms eliminate morning queues, while multiple living areas provide quiet corners for reading and game rooms for children. The secure 30-hectare estate allows supervised exploration, and the Roman-stepped pool design ensures safe access for all ages. Baby cots and high chairs are provided, and the fully equipped kitchen supports self-catering for larger groups.

Two well-behaved pets are welcome, making this an ideal choice for families traveling with four-legged companions. The unfenced garden provides freedom for pets while the extensive grounds offer endless exploration opportunities.

Property Details

This exceptional Italian villa rental operates seasonally with heating available November through early April for additional cost. Weekly housekeeping, linen changes, and private chef services are available upon request. The property includes complimentary WiFi, satellite television, washing machine, and private parking. A small active chapel on the estate adds historical significance to this protected heritage property.

The villa’s 1.3-kilometer private access road ensures complete privacy while remaining conveniently located near amenities. Essential services including supermarkets and restaurants lie within 3-4 kilometers, while recreational facilities including golf courses and tennis courts are easily accessible.

Best For

This remarkable estate suits discerning travelers seeking authentic Tuscan experiences in luxurious surroundings. Wine enthusiasts will particularly appreciate the on-site tastings and proximity to celebrated vineyards. The villa excels for milestone celebrations, romantic getaways, and cultural immersion holidays. Its combination of historical significance, modern amenities, and spectacular natural setting creates an unparalleled Chianti experience.

Frequently Asked Questions

What are the check-in and check-out times?

Check-in begins at 16:00 and check-out is required by 10:00. Late arrivals after 21:00 incur a 100 Euro surcharge payable locally.

What is the pet policy for the villa?

Up to two well-behaved pets are welcome. The extensive grounds provide ample space for exercise, though the garden areas are not fenced.

Which is the nearest airport and how far is it?

Florence Airport (FLR) is 27 kilometers away, approximately 30 minutes by car. Pisa Airport (PSA) is 74 kilometers distant, roughly one hour and 15 minutes drive time.

What is included with the villa rental?

The rental includes private pool access, WiFi, satellite TV, washing machine, parking, garden furniture, barbecue facilities, and baby equipment. Heating, housekeeping, and chef services are available at additional cost.

How far is the nearest town?

San Casciano Val di Pesa town center is 4 kilometers away, with shops, restaurants, and local services. Florence is 22 kilometers north for major attractions and cultural sites.

Is there a minimum stay requirement?

Minimum stay requirements vary by season. Weekly rentals are standard during peak summer months, while shorter stays may be available during shoulder seasons.