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This top-floor penthouse in Montepulciano is located within the town, offering convenient access to cultural sites such as the Civic Museum and art studios, and shopping destinations like Piazza Italia.
This 400 square meter residence features four bedrooms, four bathrooms, and a 10-guest capacity, boasting a glass-enclosed terrace with seating, a fully equipped kitchen, and air conditioning, with pets and families welcomed.

This recently renovated flat is located in the heart of Montepulciano, just 600 metres from the Piazza Grande and 400 metres from the Porta al Prato, offering easy access to the town's attractions. The property has received excellent ratings for location, cleanliness and user experience.
The apartment has a spacious open-plan living area with a kitchenette, ideal for families or groups of up to four people. It comes equipped with modern amenities like a dishwasher, microwave, coffee maker, TV, and free Wi-Fi, ensuring a comfortable and convenient stay.

This two-bedroom apartment is situated in a converted 800-year-old monastery, just 3 kilometres outside Montepulciano, close to the town's renowned Vino Nobile wine producers.
The self-catering property sleeps four guests and features a spacious lounge with a fireplace, a dining area, two en-suite bedrooms, a fully equipped kitchen, and access to a seasonal swimming pool, sprawling gardens, and a private 3.2-kilometre running/walking trail through the surrounding countryside.

This apartment is ideally located in the centre of Montepulciano, within a 5-minute walk of the Civic Museum and Palazzo Ricci, and just steps away from the Val di Chiana, Cantina del Redi, and Palazzo Comunale. The surrounding area is steeped in history and offers easy access to the town’s main attractions.
This 68 square metre apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment comes with a fully equipped kitchen, free Wi-Fi, a TV, laundry facilities, and designated smoking areas, as well as parking.

Agriturismo Cavalierino is located in the countryside outside Montepulciano, about 4.6 miles from the town's thermal baths and 31 miles from Mount Amiata, offering a peaceful escape from the bustling town centre. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property features a swimming pool, jacuzzi, terrace, garden, and fitness centre, providing ample opportunities for relaxation and recreation. Guests can enjoy a daily Italian breakfast and select rooms offer kitchenettes, allowing for self-catering options.

Opio 47 is a one-bedroom apartment situated on Corso principale, the main street of Montepulciano, just 100 metres from Piazza Grande, the town's historic heart. This self-catering property can accommodate up to five guests, with a double bed on the lower level, a single sofa bed and two single beds on the upper level, and boasts a private terrace.

Podere Il Conventino, a self-catering apartment in Nottola, offers convenient access to Montepulciano Terme (8.4km) and Bagno Vignoni (24km), both renowned for their thermal springs.
This one-bedroom, one-bathroom property features a private garden, swimming pool, Jacuzzi, and spa, plus free parking and outdoor amenities including a barbecue, patio, and fireplace; it sleeps up to two guests and is family-friendly, accepting pets.

Villa San Biagio, situated in the Orcia Valley, is a 3km walk from Montepulciano and within easy driving distance of other Tuscan towns such as Cortona (34km) and Montalcino (37km).
This seven-bedroom, seven-bathroom property sleeps fourteen guests, offering a private pool, garden, Jacuzzi, and well-equipped kitchens in the main house and a separate building; on-site services include winery tours and e-bike rentals.

Agriturismo Collina degli Ulivi, a self-catering apartment in Sarteano, Tuscany, enjoys a tranquil setting 14km from Montepulciano Terme, 31km from Bagno Vignoni and Bagni San Filippo, and 48km from Mount Amiata, offering stunning mountain and lake views.
This family-friendly property features a terrace, garden, parking, air conditioning, and access to a sun terrace, outdoor fireplace, children's play areas, and organised cycling and walking tours, with packed lunches available for day trips.

Villa Svetoni Wine Resort is located in Montepulciano, just 13 kilometres from the thermal baths of Montepulciano Terme, and 29 kilometres from Bagno Vignoni and Bagni San Filippo, offering a peaceful retreat in the heart of Tuscany's rolling hills. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
This charming property features a range of modern amenities, including a swimming pool, a fitness centre, and a spa, perfect for relaxation and rejuvenation. Guests can also enjoy a variety of activities on-site, such as wine tasting, bike rentals, and tennis, or simply unwind on the terrace or in the garden.

This charming flat is situated in Montepulciano, just 3.3 miles from the Montepulciano Terme spa complex, offering a tranquil setting close to the town's attractions. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment provides comfortable accommodation for up to four guests, with two bedrooms, one bathroom, and a spacious 100 square metre living area. Guests can enjoy a private balcony, a fully equipped kitchen, free Wi-Fi, and the option to rent bicycles to explore the surrounding countryside.

La Torre, near Torrita di Siena, is conveniently located 16km from Montepulciano Terme and 45km from Piazza Grande, offering easy access to regional attractions.
This recently renovated 75 square metre house boasts a private entrance, outdoor dining area, fully equipped kitchen with dishwasher, swimming pool, and garden, perfect for a family holiday.

This duplex penthouse apartment is situated in the historic centre of Montepulciano, offering immediate access to restaurants, wine cellars, and the Italian language school, with panoramic views of Tuscan vineyards and countryside. The accommodation sleeps four guests across two bedrooms and one bathroom, featuring a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, alongside a garden and a rooftop terrace.

Podere Barbetti is a charming holiday home located in the Val d'Orcia, just a short distance from the picturesque towns of Chianciano Terme, Montepulciano, and Sarteano. The property has received excellent ratings for location, cleanliness and overall user experience.
The property offers five bedrooms and two bathrooms, comfortably accommodating up to eleven guests. Guests can enjoy a spacious outdoor area with a barbecue, a garden, and stunning views of the rolling hills and vineyards of the Val d'Orcia.

Holiday rental for 7 people with an excellent rating of 93% based on 3 reviews. This accommodation is based in Montepulciano.
Facilities and services: a kitchen, a washing machine and a dish washer. This apartment is very convenient for families.

Villa Nobile, a restored 12th-century tower house, enjoys a stunning location below Montepulciano, offering easy access to the town's amenities and attractions.
This luxurious five-bedroom, six-and-a-half-bathroom property sleeps up to 14 guests and boasts a heated infinity pool, ten acres of landscaped gardens, a fitness centre, and ample parking; it provides a unique blend of historical charm and modern luxury.