Holiday rentals in Montescudaio

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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 seeking 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!

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful Chianti hills in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you will find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards with unique sunsets.

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.

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Countryside apartment in villa close to the beach

Montescudaio, one of the most beautiful villages in Italy and located in the Val di Cecina, is the setting for the Agriturismo Il Polveraio, located in the open countryside and in the middle of an olive grove, with a view of the nearby Tyrrhenian Sea and the Tuscan Archipelago. The agriturismo offers various accommodations located in the main house, dating back to the 11th century AD, and in two outbuildings and will allow you to experience a stay in total peace and tranquillity.

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.

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

L’Incanto Cozy Studio in Medieval Borgo with Patio

Step into the medieval charm of Montescudaio, inside the historic borgo right below the Abbey walls. This cozy renovated studio is perfect for couples or solo travelers. It features a bedroom, kitchenette, private bathroom and a private patio right in front of the entrance, with views over the hills and sea. Fast WiFi, Smart TV, air conditioning, mini-fridge and coffee machine. Just minutes from the beach, ideal base for Pisa, Volterra, Bolgheri, Siena and Florence.

Casetta Sole View over Tuscany Hills and Sea

Casetta Sole is a cozy Tuscan home with equipped garden, at the foot of Montescudaio village, Costa degli Etruschi, a step from the countryside. View over green hills, vineyards, olive groves and sea in the valley. Super-fast Wi-Fi (ideal for smart working), free parking + EV charging station. Garden with barbecue. Few km from the sea, on the Wine Route: near Volterra and San Gimignano, perfect for relaxation, wine tours and DOC tastings. Welcome to our Tuscany!

The cypress

Dependance of 30 sqm new building located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are within easy reach. A half-hour drive from Volterra. The furnishings are completely new. Garden and swimming pool with sea view available for guests.