Vacation rentals in Monticiano

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!

Location · Family · Decor

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Value · Location · 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.

Value · Location · Indoor 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.

Value · Location · Outdoor 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

Family · Location · Access

Tuscan Family Retreat with Garden

Iesa, lovely house with 3 bedrooms, garden, barbecue and hammock. The house is located in a quiet area, ideal for those looking for a relaxing holiday surrounded by nature. The garden offers an ideal outdoor space for outdoor lunches and dinners, with a barbecue area perfect for grilling with friends. The Terme di Petriolo are a 10-minute drive away, while Siena is a 30-minute drive away. PLEASE NOTE: the outdoor hot tub will be available from June 1 to September 15.

Location · Value · Indoor spaces

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.

Value · Family · Cleanliness

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 · Wifi

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

Value · Family · Hospitality

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Family · Location · Quiet

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.

Value · Location · Nearby

"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).

Location · Value · Wifi