Holiday rentals in Monteresi

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, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little slice of paradise!

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.

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Three-room apartment with courtyard for 4 people 5 min. from the center Yes

Three-room apartment for 4 people on the ground floor, independent with private terrace, large kitchen, washer-dryer, dishwasher. Double bedroom, another space with privacy that houses a double bed. Large bathroom with shower. Air conditioning or heating EXTRA cost calculated according to consumption. Satellite TV, WIFI and outdoor Jacuzzi. From "Antica Fonte" it is easy to visit Siena (2 km); Monteriggioni 9 Km - The hot tub closes on October 2nd and reopens on May 1st.

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.

Loggiato di Lorena - Along the Via Francigena

❤ Loggiato di Lorena ❤ ✔ Prestigious apartment (100 m²) in a historic residence overlooking the Sienese hills ✔ Very quiet and relaxing environment ✔ Free and reserved parking on site ✔ 5-minute drive from the historic village of MONTERIGGIONI and STOMENNANO ✔ VIA FRANCIGENA track for excursions: E-Bike rental and horse riding nearby ✔ Fast and FREE Wi-Fi ✔ SmartTV ✔ Suitable for remote working ✔ 15 minutes by car from the center of SIENA

Relay moderno a Siena

This elegant accommodation, just 5 km from the center of Siena, is close to the city and Chianti. Suitable for couples who love relaxation, families and sportsmen (perfect starting point for Chianti tours). The accommodation includes two double bedrooms and a study room with sofa bed, two bathrooms with shower and a half bathroom. Large and free parking, garden with solarium space, grass soccer field, guarded and covered shelter for bicycles.

Il Vecchio Noce

In the ancient rural complex of Caggio, “Il vecchio noce” offers a fully renovated apartment (recently, this past winter 2025/26) that can accommodate 2 to 4 people. The complex is located in the heart of the Tuscan countryside, on the Montagnola Senese, near the medieval village of Monteriggioni and the route of the Via Francigena. The accommodation is known as the village's "granaio" (granary) as it faces south and is on the ground floor.

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.

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Siena Countryside Colle Ciupi

Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden