Villa Cipresso Casciano Tuscany: 7-Bedroom Villa with Spa and Val d’Orcia Views in Tuscany, I

This exceptional luxury villa rental Tuscany offers a refined escape in the rolling countryside near San Casciano dei Bagni, one of southern Tuscany’s most celebrated medieval spa towns. Villa Cipresso Casciano Tuscany accommodates up to twelve guests across a beautifully restored main villa and a separate guest house, creating an atmosphere of understated elegance amid the timeless landscapes of the Val d’Orcia. With seven bedrooms, seven bathrooms, private spa facilities, and sweeping views across olive groves and green valleys, this is a property that invites slow living and meaningful gatherings.

Inside Villa Cipresso Casciano Tuscany

Step through the entrance of the main villa and you are greeted by a generous living room where soft linen sofas frame a traditional stone fireplace. A curated media library, Netflix access, and an integrated sound system ensure quiet evenings are just as enjoyable as sun-filled days. The room flows naturally into a dining area with seating for twelve, perfect for long Italian suppers prepared with ingredients sourced from nearby markets. The fully equipped kitchen features modern appliances and ample counter space, designed for both casual cooking and more ambitious culinary endeavors. A private office on the ground floor provides a discreet workspace for those who need to stay connected during their holiday.

On the ground floor of the main villa, two bedrooms offer immediate comfort. The first features a queen-size bed and an ensuite bathroom complete with bathtub and overhead shower. The second bedroom mirrors this sense of luxury with its own refined ensuite. Upstairs, additional bedrooms continue the villa’s design language of warm terracotta tiles, exposed wooden beams, and crisp white linens against muted earth tones. Each room feels private and peaceful, with windows that frame the countryside like living paintings.

The guest house extends the accommodation with its own distinct character, offering independent living spaces that give visiting friends or extended family members a welcome sense of autonomy. Every bedroom across both buildings maintains the same high standard of finish, with quality mattresses, generous wardrobes, and thoughtful touches such as reading lamps and soft throws.

Outdoor Spaces and Living

The outdoor areas at Villa Cipresso Casciano Tuscany are designed for long days spent between sun and shade. A swimming pool sits at the heart of the grounds, surrounded by stone terracing and sun loungers that look out across undulating hills dotted with cypress trees and vineyards. A shaded al fresco dining area makes it easy to serve meals outdoors, and the built-in barbecue invites casual grilling sessions with a glass of Brunello in hand.

Beyond the pool, manicured lawns give way to a more natural landscape of Mediterranean planting and mature trees, offering pockets of shade for reading or quiet conversation. The spa and sauna facilities provide a layer of indulgence that elevates this luxury villa rental Tuscany beyond the ordinary, allowing guests to unwind after a day of exploring hill towns or cycling through country lanes. Private parking ensures easy access for those arriving by car, and the sense of seclusion is immediate upon arrival, even though the charming streets of San Casciano dei Bagni are only a short drive away.

Exploring the Tuscan Countryside and Beyond

San Casciano dei Bagni, just minutes from the villa, is renowned for its natural thermal springs, which have drawn visitors since Etruscan and Roman times. The town itself is a quiet treasure of stone-built houses, artisan shops, and intimate restaurants serving traditional Tuscan cuisine. The elegant Fonteverde thermal resort is nearby for those seeking a day of professional wellness treatments.

The Val d’Orcia, a UNESCO World Heritage landscape, unfolds in every direction. Pienza, famous for its Renaissance architecture and pecorino cheese, is approximately 40 minutes by car. Montepulciano, home to the celebrated Vino Nobile, sits about 30 minutes away and rewards visitors with panoramic views and exceptional wine cellars. The medieval city of Siena, with its iconic Piazza del Campo, is roughly an hour’s drive north. For a broader exploration of this remarkable region, explore our luxury villas in Tuscany to discover more options across the area.

The Umbrian border is also close, opening up possibilities for day trips to Orvieto, roughly 45 minutes south, where a magnificent Gothic cathedral crowns the hilltop town. Lake Trasimeno, a peaceful expanse of water popular for swimming and sailing, lies within easy reach as well. To see what else awaits across the country, check our full collection of villas in Italy for properties spanning coastline to countryside. You can also browse our wider area listings for additional Tuscan retreats.

Perfect for Families and Groups

The combination of a main villa and a separate guest house makes Villa Cipresso Casciano Tuscany particularly well suited to multi-generational families or groups of friends traveling together. Children will enjoy the freedom of the gardens and the pool, while parents can relax nearby with full visibility of the outdoor spaces. The countryside setting provides a safe and stimulating environment for younger guests, with opportunities for nature walks, visits to local farms, and gelato excursions in nearby towns.

For groups, the generous living and dining areas encourage togetherness without sacrificing privacy. The separate guest house allows couples or smaller family units to maintain their own rhythm, retreating to their own space when they wish. The kitchen is large enough to accommodate collaborative cooking, and the dining table for twelve means everyone can sit down together for a proper Tuscan feast. Air conditioning throughout ensures comfort during the warmer summer months, and the WiFi connection keeps everyone linked to the outside world when needed.

Property Details and Practical Information

Villa Cipresso Casciano Tuscany sleeps up to twelve guests in seven bedrooms, each with its own ensuite bathroom. The property includes air conditioning, WiFi, a washing machine, a fully equipped kitchen, a barbecue, a fireplace, private parking, and spa and sauna facilities. The grounds feature a swimming pool, landscaped gardens, and outdoor dining areas. The main villa and guest house together provide ample communal space alongside private retreats. Bed linens, bath towels, and pool towels are provided, and the property is cleaned and prepared before arrival.

Best For

This luxury villa rental Tuscany is ideal for: multi-generational families seeking a comfortable and spacious countryside retreat, groups of friends celebrating milestones surrounded by world-class wine country, couples traveling together who value privacy and refined surroundings, and wellness enthusiasts drawn to the thermal heritage of San Casciano dei Bagni.

Frequently Asked Questions

Q: What is the nearest airport and transfer time?

A: The nearest major airports are Rome Fiumicino (approximately two hours by car) and Florence Peretola (around two hours and fifteen minutes). Perugia San Francesco d’Assisi Airport is closer, roughly one hour and fifteen minutes away, with limited international connections. Private transfers can be arranged upon request.

Q: What is the best time to visit?

A: Southern Tuscany is glorious from late April through October. May and June bring wildflowers and comfortable temperatures, while September and early October offer harvest season, truffle hunting, and golden light across the Val d’Orcia. July and August are warmest, ideal for pool days and long evenings outdoors.

Q: What is the minimum stay?

A: The minimum stay is typically seven nights during peak summer season (June to September), with shorter stays of three to five nights sometimes available during spring and autumn. Please enquire for specific dates.

Q: What is included in the rental?

A: The rental includes all utilities, air conditioning, WiFi, bed linens, towels, pool towels, use of the spa and sauna, barbecue facilities, and private parking. A welcome pack and end-of-stay cleaning are also included. Additional services such as private chefs, grocery pre-stocking, and guided excursions can be arranged at extra cost.

Q: Is there a supermarket nearby?

A: A small grocery shop and bakery can be found in San Casciano dei Bagni, just a few minutes’ drive from the villa. For larger supermarkets, the town of Chiusi, approximately 20 minutes away, offers several options including a Coop supermarket with a wide selection of local and international products.

Q: Can guests use the thermal springs nearby?

A: Yes. San Casciano dei Bagni is home to over 40 natural thermal springs. Some are accessible as free open-air bathing spots along the hillside, while the Fonteverde resort offers a premium spa experience with thermal pools, treatments, and wellness programs. The villa’s own spa and sauna facilities also provide a private alternative for relaxation without leaving the property.