Villa Chiantigiana San Casciano: Luxury 5-Bedroom Villa with Private Pool and Family-Friendly Features, Chianti

This luxury villa rental Chianti offers a serene retreat amid Tuscany’s famed vineyards and rolling hills. Located near San Casciano in Val di Pesa, this elegant house provides an authentic Tuscan experience with five bedrooms, six bathrooms, and ample space for up to eight guests.

Inside This Luxury Villa Rental Chianti

The interior of the villa reflects classic Tuscan charm with a traditional décor that embraces rustic wood furnishings, terracotta floors, and warm tones throughout. The main living area is spacious and inviting, featuring comfortable seating arranged around a fireplace, ideal for relaxing evenings. The fully equipped kitchen is functional and well-appointed, perfect for preparing meals with local ingredients. All five bedrooms are located on the first floor, offering privacy and restful nights; guests should note that stairs are required to access these rooms. Bathrooms maintain a consistent style and quality, even though not all have been photographed. Opposite the main house, a charming stone barn houses a second kitchen, dining area, and living room, providing an excellent space for family gatherings or separate entertaining.

Outdoor Spaces and Tuscany Setting

The villa’s outdoor areas are equally captivating, featuring a private swimming pool open from June through the end of September. Surrounded by manicured gardens and olive trees, the pool terrace is perfect for sunbathing or enjoying alfresco meals with panoramic views of the Chianti countryside. Several shaded terraces and dining areas invite guests to savour the tranquil atmosphere and breathtaking vistas. Ample free parking is available for up to four cars, an important convenience given the rural location.

Exploring Chianti and the Local Area

Situated less than an hour’s drive from the historic city of Siena, this villa offers access to the heart of Tuscany’s wine country. Nearby San Casciano in Val di Pesa provides authentic markets, charming cafés, and traditional Tuscan restaurants. Guests can explore the surrounding vineyards, participate in wine tastings, or visit notable towns such as Greve in Chianti and Castellina in Chianti, all within easy reach. For cultural excursions, Florence is approximately 30 minutes away by car. Due to the uneven and unpaved access road, a high-clearance vehicle is recommended for comfortable travel. Explore our full collection of luxury villa rentals in Chianti.

For more on what to see and do, visit the Chianti tourism guide.

Perfect for Families and Groups

This villa is ideal for families and multi-generational groups, with its generous living spaces and a separate barn that offers both privacy and communal gathering areas. Children are warmly welcomed, and the host can provide a cot and high chair upon request, making it a practical choice for guests travelling with little ones. The large outdoor pool and safe garden areas offer plenty of space for play and relaxation, while the peaceful countryside setting ensures a restful stay for all ages.

Property Details and Practical Information

The villa accommodates up to eight guests across five bedrooms and six bathrooms, all thoughtfully maintained to ensure comfort. Parking is available free of charge for up to four vehicles. Guests should be aware that all bedrooms are located on the first floor, requiring stair use. The swimming pool is usable from June until the end of September. Access to the property involves an unpaved, uneven road, so hiring a car with good clearance is highly recommended. The host offers family amenities such as a cot and high chair on request. Some ground floor rooms remain private and are excluded from guest access. For more options, browse our luxury villa rentals in Italy.

Best For

This Chianti House is ideal for: families seeking a spacious and child-friendly Tuscan retreat, multi-generational groups celebrating special occasions, wine enthusiasts exploring the Chianti region, and guests looking for a peaceful countryside villa with private pool access and authentic local character.

Frequently Asked Questions

Q: What is the nearest airport and how long is the transfer?

A: Florence Airport (FLR) is the closest, approximately 30 minutes by car. Pisa Airport (PSA) and Rome Fiumicino (FCO) are also options but require longer transfers.

Q: When is the best time to visit?

A: Late spring through early autumn is ideal, especially June to September when the pool is open and the countryside is vibrant.

Q: What is the minimum stay at this villa?

A: The minimum stay is one night, offering flexible booking options for shorter visits.

Q: What amenities are included with the rental?

A: The villa includes full kitchen facilities, six bathrooms, private pool access, free parking, and family amenities like a cot and high chair on request.

Q: Where is the nearest supermarket?

A: The closest supermarket is in San Casciano in Val di Pesa, about 10 minutes’ drive from the villa.

Q: Is a car recommended for this property?

A: Yes, hiring a car with high clearance is strongly recommended due to the unpaved and uneven road leading to the villa.