Holiday houses in Monticiano

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

Location · Family · Nearby

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Location · Family · Pool

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.

Family · Value · Quiet

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Family · Location · Outdoor spaces

Il TramontO

The TramontO is a completely renovated elegant and rustic apartment surrounded by the nature of Tuscany, with panoramic views, garden, terrace and mini-whirlpool for exclusive USE. Many details in natural wood and antique stone stand out. A few steps from the Abbey of San Galgano, which can also be reached by an enchanting path 5 km from the village. 35 km from Siena and 92 km from Florence, built from a historic tower from the 1200s, it offers charm, relaxation and unforgettable sunsets.

Location · Family · Indoor spaces

Typical Tuscan Cottage with swimming pool and park

The Country Cottage is located in the heart of authentic Tuscany, in an unspoiled area, with a unique biodiversity. Located just a 5-minute drive from the famous Abbey of San Galgano and the Hermitage of Montesiepi, where the prestigious "Sword in the Stone" is kept. The entire property is rented: the typical Tuscan country house, the swimming pool, the garden and the fenced park. A perfect location to relax with maximum privacy, without the stress and wear and tear of modern life

Value · Location · Wi-Fi

small apartment

The apartment is located on the first floor of an early 20th century building, in the historic center of the municipality of Monticiano. The entrance opens onto a room with a small kitchen. In the apartment there are two small bedrooms. In the first bedroom, the queen-size bed (1.40x2.00 m) is hanging off the ground approximately 1.70 m high. The second bedroom has a single bed equipped with a pull-out extension that allows it to be transformed into a double bed.

Family · Value · Kitchen

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Family · Location · View

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Location · Family · Barbecue

Independent country house with private pool

Situated in a panoramic position overlooking a green landscape of wooded hills, this beautiful stone house, surrounded by a wide fenced garden, has been restored and furnished simply and comfortably for holiday use. The house is surrounded by a wide fenced garden where the pool is set (6x 12 m – depth from 1,20 to 1,50m, seasonal opening) and guests have a covered loggia furnished with table and chairs for outside dinners.

Family · Value · Heating

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.

Location · Value · Hot tub

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Value · Family · Biking