Villas and Holiday homes in Pienza

This chalet in Trequanda is located near cultural sites such as the Artemisia Gallery and Palazzo Borgia, and historical landmarks including Chiesa di San Francesco and Palazzo Piccolomini, offering a gateway to the region's heritage.
This 93 square meter property accommodates up to four guests across two bedrooms and two bathrooms, featuring a well-equipped kitchen, air conditioning, Wi-Fi, a swimming pool, and a terrace, with parking available.

Villa il Moro, a spacious 550 square metre property in Montalcino, Tuscany, is situated 45km from Siena’s Piazza del Campo and within easy reach of other Tuscan towns such as Bagno Vignoni.
This five-bedroom, six-bathroom villa sleeps up to 19 guests and boasts a private swimming pool, terrace, garden, free Wi-Fi, and ample parking, ideal for large families or groups seeking a self-catering holiday with access to hiking and cycling in the Tuscan countryside.

Villa Sambuco, a luxury Tuscan property near Sarteano, enjoys stunning 360° views of the Val d'Orcia, a UNESCO World Heritage site, and is situated between Sarteano and Radicofani in the Valdichiana and Val d'Orcia regions.
This six-bedroom, seven-bathroom villa sleeps 13, boasts a heated infinity pool, private gym, extensive gardens, and features a fully equipped kitchen, including a dishwasher; guests can also enjoy fresh produce from the on-site vegetable garden, henhouse, and orchard.

Agriturismo Le Macchie is a 5-minute drive from Monticchiello and 8 kilometres from Montepulciano, in the Tuscan countryside near the Lucciolabella Nature Reserve and Valdorcia Nature Park. This farm stay has received excellent ratings for its location, cleanliness and overall experience.
The property offers a choice of apartments, each with a private patio and garden area. Guests can enjoy a refreshing dip in the outdoor pool, relax in the jacuzzi, and prepare meals in the fully equipped kitchens.

Agriturismo La Poderina is a farm stay located just 0.6 miles from the spa town of Bagno Vignoni and a 20-minute drive from Montepulciano, set in the peaceful countryside of Castiglione d'Orcia. It has received excellent ratings for location, cleanliness, and user experience. The accommodation offers self-catering apartments with exposed-beam ceilings, creating a warm and inviting atmosphere. Guests can enjoy free Wi-Fi, on-site parking, BBQ facilities, and a swimming pool, as well as a terrace or balcony and a garden.

Agriturismo Villa Mazzi is situated in the Tuscan countryside, 30 kilometres from Castiglione del Lago on Lake Trasimeno and a one-hour drive from Arezzo. This farm stay has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The self-catering apartments offer a peaceful retreat in a rustic setting. Guests can enjoy a garden with barbecue facilities, homemade olive oil, jam, and honey, and free Wi-Fi access.

Villa Monticelli, part of the Away from the Flock brand, is a six-bedroom luxury property situated in the Tuscan countryside between Sarteano and Radicofani, offering breathtaking views of the Val d'Orcia.
This spacious villa sleeps 13 guests and boasts an infinity pool, two-acre grounds, a fully equipped kitchen with two dishwashers and two ovens, and access to on-site activities including cooking classes and cultural excursions.

This luxurious Montalcino castle enjoys a convenient location just steps from the Val di Chiana valley, 3.6km from the Saints Peter and Andrew Church, and within 10km of the Sant'Anna in Camprena Monastery and San Giovanni d'Asso railway station.
This 4-bedroom, 4-bathroom property sleeps 8 guests and boasts a Jacuzzi, sauna, garden, terrace, and fully equipped kitchen including a dishwasher; barbecue facilities are also available for al fresco dining.

This expansive villa, situated in the Montepulciano countryside, offers easy access to the town's attractions, a short drive from the historic centre.
This 450 square metre property boasts seven en-suite bedrooms sleeping sixteen guests, two fully equipped kitchens, multiple living areas with fireplaces, extensive gardens totalling 3300 m², a swimming pool, jacuzzi, and ample parking.

Villa Cielo is a spacious 160 square meter house situated within the Cignella Resort in Trequanda, offering panoramic views of the Tuscan hills and resort amenities. This family-friendly villa accommodates up to six guests across three bedrooms, featuring air conditioning, internet, a fully equipped kitchen with a fridge, and a private garden or terrace, with the option to use the resort's communal swimming pool.

Podere La Paolina is a farm stay situated in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering easy access to the Valdichiana and the beautiful Tuscan countryside. The property has received excellent ratings for cleanliness and location, making it a popular choice for travellers seeking a relaxing escape.
The accommodation offers a choice of rooms and self-catering apartments, all with private entrances and soundproofing for a peaceful stay. Guests can enjoy stunning garden views, a swimming pool, and a restaurant serving delicious Italian cuisine, as well as take advantage of the on-site yoga sessions, bicycle rental, and convenient amenities like free Wi-Fi and parking.

Vitalenta Agriboutique, near Chianciano Terme, offers a convenient base for exploring Tuscany, situated 14 kilometres from Montepulciano Terme and within 16 and 18 kilometres respectively of Bagno Vignoni and Bagni San Filippo.
This Pienza countryside property provides a 25 square metre one-bedroom, one-bathroom self-catering apartment sleeping up to three guests, complete with air conditioning, a garden, on-site restaurant and bar, room service, free parking and Wi-Fi.

Agriturismo Torrenieri da Alessandro is situated in the Val d'Orcia, a short drive from the picturesque towns of Pienza, San Quirico d’Orcia, and Montepulciano. The property enjoys excellent ratings for its location, cleanliness, and overall guest experience.
The self-catering apartments offer a traditional Tuscan ambiance, with wood-beamed ceilings and terracotta floors. Guests can enjoy on-site olive oil production, complimentary bikes for exploring the area, a garden with BBQ facilities, and breakfast essentials provided in their accommodation.

Podere Travagliola is a farm stay located in Castiglione d'Orcia, just 5.6 km from the thermal baths of Bagno Vignoni and 33.8 km from Mount Amiata, offering a peaceful escape in the Tuscan countryside. This property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The farm stay features a single bedroom and bathroom, covering 13 square metres and accommodating up to 2 guests. Guests can enjoy a fully equipped kitchen, air conditioning, a garden, and free parking, along with scenic views and opportunities for hiking and cycling in the surrounding area.

This charming self-catering cottage is located in Torrita di Siena, just a short drive from the Val di Chiana and within a 15-minute drive of The Saints Peter and Andrew Church and the Monastery of Sant'Anna in Camprena, offering a tranquil escape in the heart of Tuscany. The property has received excellent reviews from previous guests, highlighting its peaceful setting and authentic rural charm.
The cottage spans 90 square metres and comprises two bedrooms and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests can enjoy access to a private terrace or balcony, a swimming pool, and barbecue facilities, as well as a fully equipped kitchen with a fridge and microwave oven.

Villa Mulinello, near Montepulciano (16km from its thermal baths), offers a peaceful Tuscan retreat close to Torrita di Siena, with Bagno Vignoni and Bagni San Filippo further afield at 26km and 37km respectively.
This 93 square metre property boasts three bedrooms, two bathrooms, and sleeps six, featuring a fully equipped kitchen, terrace, garden, free parking, and Wi-Fi; barbecue facilities are also available for al fresco dining.