Holiday rentals in Monteriggioni

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.

Tuscany-Monteriggioni- Chianti- Francigena-

The apartment is a portion of a typical Tuscan farmhouse, formerly a mill (the oldest part dates back to around 1200) and is surrounded by nature and in a strategic position on the Via Francigena, 2 km from Monteriggioni, 10 km from Siena and close to San Gimignano, Volterra and Florence. The apartment consists of an equipped open kitchen, bathroom with shower, bedroom with double bed and bedroom with two single beds. The living area has a comfortable sofa bed with TV, Wi-Fi and air conditioning

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

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.

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

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.”

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Open Space Piscina e Giardino

La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Breathtaking sunsets in Tuscany | View and relaxation

Benvenuti a Il Poggiolo, una casa vacanze dal sapore autentico immersa nel cuore della Toscana, a pochi chilometri da Siena. Situata in una posizione panoramica tra dolci colline e paesaggi da cartolina, questa dimora è perfetta per chi cerca tranquillità, bellezza e tradizione. tutti gli ospiti che hanno soggiornato si sono innamorati del panorama e della tranquillità che si respira a due passi da tutte le mete del nostro territorio.

The Almond Tree of Monteriggioni

Independent apartment within an ancient farmhouse overlooking the Via Francigena. The kitchen is equipped with a refrigerator, stove and kettle. The room is bright with a king-size mattress. Green area with table and chairs available. The castle of Monteriggioni is within walking distance. The property is equipped with a stable where you can book scenic horseback riding. Intermediate location between Siena and San Gimignano.

Giulia - Romantic bedroom in Monteriggioni

A romantic room in the heart of Monteriggioni, a XII century medieval village on the Francigena way, an ancient walking trail that takes pilgrims from Canterbury to Rome. The room overlooks the main square of the village and offers our guests the unique experience of standing in one of the most beautiful villages in Tuscany!