Vacation rentals in Il Cipresso

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Collina Power

Collina is an ancient stone farmhouse, the house is surrounded by fields and olive groves. It has a large garden with swimming pool and a terrace where you can have pleasant lunches and dinners. A barbecue and garden furniture are available. The road to get to the house in the last stretch is not paved and is therefore not suitable for sports cars or particularly low ones. The route lends itself to pleasant walks during the day, while at night we recommend using a car because it is not lit.

LOFT with a view located in the heart of Volterra

Small loft with independent entrance located in the heart of Volterra, ideal for a couple who decides to enjoy the magical atmosphere of the city for a few days. Every choice inside is designed to give guests a precious setting. The view of the sunsets over the sea of the Tuscan archipelago offers the romantic canvas on which to imprint unique memories. The warmth of the wood, the solidity of the stone and the brilliance of the crystal perfectly describe the owner's concept of Home.

Piazzetta N20 Apartment

Positioned in one of the most suggestive locations of Volterra, the apartments is a wonderful place, full of natural light and surrounded by a breathtaking landscape. Placed in the old part of the town, inside the medieval walls, the property is one of two apartment that lie within the same building; it’s composed by a large open space with cooking facilities completely equipped and a living room, a double bedroom, a bathroom with shower. Clima is present. Free Wi-Fi Is available

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Studio in the historic center of Volterra

In the historic center (200 m from the main square), it is equipped with: a kitchen area; a living room with a double sofa bed (200x160, memory foam mattress) and a sofa bed; and a bathroom with a walk-in shower. Naturally cool thanks to the thick walls of the historic building in which it is located, it does not require air conditioning. It is located on the ground floor, with an independent entrance.

Charming Tuscan Villa with pool

Nestled on a panoramic hill and located just 3.8 km from the historic city of Volterra, Podere Casalino is easily accessible via a paved road and has private parking onsite. This traditional Tuscan farmhouse is set in the Volterra countryside, and was completely restored and preserved 25 years ago and updated again in late 2024. A new kitchen has been installed in Spring 2025.

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.