Villas in Pienza

19 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Pienza villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

19 Villas in Pienza

Best villas and farmhouses in Pienza with a pool

Among the 19 villas in Pienza, here are the 4 best villas with a pool

Villa "La Memoria Del Tempo "With A/c - Pienza
9.8 88 reviews

Villa "La Memoria Del Tempo "With A/c

house, Montalcino
This 15th-16th century Tuscan farmhouse, near Montalcino, boasts breathtaking views of the rolling hills and is ideally situated for exploring the region’s vineyards and medieval town.
The property sleeps up to 10 guests, features a large private garden with a swimming pool and barbecue, a fully equipped kitchen, and offers additional accommodation nearby for larger groups; bed linen, utilities (water, gas, electricity), and heating (up to €100 for stays of 2+ nights) are included.
Montalcino -Podere Tigliolo Tra Montalcino Pienza - Pienza
9.3 130 reviews

Montalcino -Podere Tigliolo Tra Montalcino Pienza

house, Castiglione d'Orcia
Il Tigliolo, a restored 19th-century rural property, offers accommodation within the Val d'Orcia natural reserve, located 3 kilometres south of San Quirico d'Orcia and 5 kilometres north of Montalcino.
This family-friendly villa, suitable for up to four guests, features two bedrooms, one bathroom, a kitchenette, and access to a large garden with a 7x15 metre swimming pool, table tennis, bocce ball, and barbecue facilities, alongside numerous walking and cycling trails.
Salcheto Winehouse - Pienza
9.4 1938 reviews

Salcheto Winehouse

farm, Montepulciano
Salcheto Winehouse is a vineyard farm located just a short 3.7-mile drive from the historic town of Montepulciano, offering a peaceful escape surrounded by rolling Tuscan hills. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farm offers a range of accommodation options, from stylish rooms to spacious apartments, all featuring modern amenities and private outdoor spaces. Guests can enjoy a variety of activities on-site, including wine tastings, exploring the traditional wine cellar, and relaxing in the heated outdoor hot tub.
Casale Il Gugnolo - Pienza
9.2 5 reviews

Casale Il Gugnolo

house, Castiglione d'Orcia
This four-bedroom villa, located in Castiglione d'Orcia, is situated 32 kilometres from Mount Amiata and 3.06 kilometres from Bagno Vignoni.
This 200 square metre holiday home accommodates up to 15 guests and offers a fully equipped kitchen, three bathrooms, a Jacuzzi, garden, terrace, fireplace, and free Wi-Fi, with bike rental and nearby cycling and walking tours available.

Best family friendly villas in Pienza

Among the 19 villas in Pienza, here are the 4 best family friendly villas

Camera Il Giardino - Pienza
10 1 review

Camera Il Giardino

gîte, Pienza
This Val d'Orcia farmhouse, a short drive from Pienza, offers a taste of authentic Tuscan life in a UNESCO World Heritage site.
The self-catering property sleeps three, boasting a bedroom, bathroom, garden access, a swimming pool, and includes complimentary breakfast and local wine tasting.
Monastero Sant'anna In Camprena - Pienza
9.6 392 reviews

Monastero Sant'anna In Camprena

farm, Pienza
Fattoria Monastero Sant'Anna in Camprena is located in the Tuscan countryside, just 19 kilometres from Bagno Vignoni and 23 kilometres from Montepulciano Terme, offering a peaceful escape from the hustle and bustle of Pienza. This farm stay has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The property features a charming restaurant, a garden and a terrace, providing ample space for relaxing and enjoying the beautiful surroundings. This farm stay can accommodate up to two guests in its comfortable and modern accommodation, which includes air conditioning, a private bathroom, a fridge, a microwave oven and free Wi-Fi.
90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Pienza
No reviews

90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Torrita di Siena
Farm listing for 4 people. You will be in Torrita di Siena.
Services and facilities include a freeze, a dish washer and a swimming pool. Take advantage of the Free Parking with this accommodation in Torrita di Siena!
90 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

90 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Torrita di Siena
This secluded rural property, offering a tranquil escape, is situated in a panoramic location near Montefollonico (1.3 km) and Montepulciano (7 km), boasting spectacular views of the Montepulciano valley, San Biagio temple, Monte Amiata, and the Val d'Orcia hills.
This holiday home, spanning 90 square meters and accommodating up to six guests, features two independent stone houses, including the restored 17th-century Casa MULINELLO with a living room, two fireplaces, and two panoramic terraces, along with a kitchen equipped with a fridge and dishwasher, and is pet and family friendly with internet and parking.

Frequently asked questions about villa rentals in Pienza

  • What are the must-see attractions in and around Pienza?

    Pienza is a real gem! You absolutely must visit the Duomo, a beautiful cathedral with stunning Renaissance architecture. The Palazzo Piccolomini is another must-see, offering breathtaking views of the Val d'Orcia. And if you're looking for a unique experience, check out the Corsignano Fortress, a medieval fortress with a fascinating history.
  • What are the best villas in Pienza?

    Among the villas in Pienza, Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Pienza?

    The Val d'Orcia is home to a variety of wildlife. You might spot deer, wild boar, and even the occasional fox. You're also likely to see a variety of birds, including hawks, owls, and woodpeckers. Keep an eye out for the local sheep, too, as they are a common sight in the area.
  • What are the best villas with a pool in Pienza?

    Agriturismo Il Macchione, Poggio Ai Gelsi and Agriturismo La Collina are the best villas with a pool in Pienza.

  • What is the best time to visit Pienza?

    Spring and autumn are the best times to visit Pienza. The weather is mild, and the crowds are smaller. You'll also be able to enjoy the stunning colours of the Val d'Orcia, especially in autumn. Summer can be very hot and crowded, while winter can be chilly and wet.
  • What are the best villas with a jacuzzi in Pienza?

  • When is it easiest to book a villa rental in Pienza?

    Booking a villa rental in Pienza is easier outside of peak season. If you're looking for the best deals, try booking in the shoulder seasons of spring and autumn. You'll find that availability is better and prices are lower during these months.
  • What are the best villas for families and kids in Pienza?

    The best villas for families and kids in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati.

  • What are the top hiking trails near Pienza?

    The Val d'Orcia is a hiker's paradise. One of the most popular trails is the Sentiero del Latte, which follows an old mule track through rolling hills and vineyards. Another great option is the Sentiero del Brunello, which takes you past vineyards and olive groves. Both offer stunning views of the Tuscan countryside.
  • What are the best pet friendly villas in Pienza?

    The best pet friendly villas in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Poggio Ai Gelsi.

  • What are the advantages of renting a house or a villa in Pienza

    Renting a villa in Pienza offers a lot of advantages. You'll have more space and privacy than in a hotel. You'll also be able to enjoy the convenience of having a kitchen and laundry facilities. Plus, you'll be able to experience the true Tuscan lifestyle, surrounded by the beauty of the Val d'Orcia.
  • What are the best villas with parking in Pienza?

    Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the best villas with parking in Pienza.

  • Are there popular destinations near Pienza?

    Absolutely! Pienza is a great base for exploring the surrounding area. You can easily take day trips to Siena, Montepulciano, and Montalcino, all within an hour's drive. Each town offers its own unique charm and attractions, from medieval architecture to world-class wineries.

Popular destinations

Best Pienza villas and holiday homes with parking

Agriturismo Il Macchione - Pienza
9.3 570 reviews

Agriturismo Il Macchione

house, Pienza
This 18th-century farmhouse is located just 0.9 miles outside of Pienza, overlooking the stunning Val d'Orcia Natural Park, offering a secluded and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse features a spacious terrace with a swimming pool and hydromassage area, perfect for relaxing and enjoying the beautiful surroundings. Guests can also enjoy a range of amenities, including a fitness center, tennis court, and a children's playground, as well as a buffet breakfast and BBQ facilities.
Bellarmino-palazzi Del Papa - Pienza
9.7 13 reviews

Bellarmino-palazzi Del Papa

gîte, Pienza
Agriturismo Palazzi del Papa, a self-catering holiday home in the Pienza countryside, offers easy access to Pienza's historic centre, including the Duomo and Piazza Pio II, although the precise distance isn't specified.
This two-bedroom, two-bathroom property sleeps four, boasting a fully equipped kitchen with a dishwasher, air conditioning, a private swimming pool, and free Wi-Fi; optional farm-fresh breakfast and dinner are available.
Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza
Farm for up to 3 people. This accommodation is based in Pienza.
Facilities and services: air conditioning, free parking and a terrace. This accommodation in Pienza has a swimming pool!
Agriturismo Cretaiole - Pienza
9.8 48 reviews

Agriturismo Cretaiole

farm, Pienza
Agriturismo Cretaiole is a farm stay located in Pienza, just 10.5 km from the charming village of Bagno Vignoni and 45 km from Mount Amiata, offering a peaceful escape in the Tuscan countryside. This property has received excellent ratings for location, cleanliness and user experience.
The farm stay offers a variety of accommodation options, including rooms with fully equipped kitchens and private entrances. Guests can enjoy a range of amenities and activities, including a garden with stunning views, a sun terrace, free Wi-Fi, parking, outdoor play equipment, bicycle rental and a concierge service.

Best Pienza villas and holiday homes with a garden

Agriturismo La Creta - Pienza
9.9 29 reviews

Agriturismo La Creta

farm, Montepulciano
Agriturismo La Creta, near Montepulciano, offers self-catering accommodation 7.7km from Montepulciano Terme and 50km from Mount Amiata.
This family-friendly property features private units with fully equipped kitchenettes, a garden, barbecue facilities, free Wi-Fi, and parking; pets are welcome.
Casa Remolina - Pienza
9.7 40 reviews

Casa Remolina

house, Torrita di Siena
Casa Remolina, in Montefollonico, offers a peaceful retreat in the Tuscan countryside, situated approximately 16km from Montepulciano Terme and 24km from Bagno Vignoni.
This 110 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, private garden, terrace, free Wi-Fi and parking.
Villa In Totona With 6 Bedrooms Sleeps 12 - Pienza
No reviews

Villa In Totona With 6 Bedrooms Sleeps 12

house, Montepulciano
This luxurious six-bedroom villa in Montepulciano is situated a short 2.4km walk from the Val di Chiana and Triacca Winery, and within 3.2km of San Biagio and Torre del Pulcinella.
The 550 square metre property boasts a private pool, Jacuzzi, sauna, spa, and fitness centre, accommodating up to 12 guests and featuring a fully equipped kitchen and six bathrooms.
70 M² House ∙ 1 Bedroom ∙ 2 Guests - Pienza
9.1 11 reviews

70 M² House ∙ 1 Bedroom ∙ 2 Guests

house, San Quirico d'Orcia
This Tuscan holiday home is situated near San Quirico d’Orcia, a short distance from the Renaissance garden at the Church of Santa Maria Assunta.
The 70 square metre property offers one bedroom, two bathrooms, sleeps four, and includes a kitchen with fridge and dishwasher, plus a garden, parking, and internet access.
©2026 cozycozy.com