Villas and Holiday homes in Pienza

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Pienza holiday homes
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19 Villa rentals in Pienza

Best Pienza villas and holiday homes with a pool

Among the 19 accommodations in Pienza, here are the 4 best villas and holiday homes with a pool

Iperbole Country House, Between Pienza And Montepulciano - Pienza
10 11 reviews

Iperbole Country House, Between Pienza And Montepulciano

house, Pienza
This charming villa is located in Pienza, a short walk from the historic centre and the Palazzo Piccolomini, in the heart of the rolling Tuscan countryside. The property has received excellent reviews from previous guests.
The villa has five bedrooms and six bathrooms, providing ample space for up to nine guests. It also boasts a large, open living area, a private garden, a swimming pool, a Jacuzzi, a terrace, and a range of other amenities.
Sangiovese 14, Emma Villas - Pienza
No reviews

Sangiovese 14, Emma Villas

house, Montepulciano
This restored stone farmhouse, Sangiovese, is located in the Val di Chiana, a short drive from Montepulciano, amid Tuscan vineyards producing Nobile di Montepulciano wine, and offers proximity to Pienza and Cortona.
This 350 sq m country house, divided into two independent units, accommodates up to 14 guests with 5 bathrooms, air conditioning, a 3,500 sq m park featuring a swimming pool and barbecue area, and opportunities for on-site wine tastings.
Villa Cielo- Cignella Resort Tuscany Accommodation - Pienza
No reviews

Villa Cielo- Cignella Resort Tuscany Accommodation

house, Trequanda
Villa Cielo, a spacious villa in Osteria Delle Noci, is located 17.7 kilometres from Montepulciano Terme and 46.7 kilometres from Piazza Grande.
This air-conditioned property offers accommodation for 11 guests with 3 bedrooms, 3 bathrooms, a fully equipped kitchen, a patio with garden views, and an outdoor swimming pool, with free WiFi available.
Hotel Apartment "Villa Limone" With Shared Pool & Wi-fi - Pienza
No reviews

Hotel Apartment "Villa Limone" With Shared Pool & Wi-fi

house, Trequanda
This villa apartment is located in Trequanda, a short drive from the Val di Chiana and the historic centre of Pienza, with Artemisia Gallery and Palazzo Borgia nearby.
This property offers 156 square meters of living space for up to 6 guests, featuring 3 bedrooms, 3 bathrooms, air conditioning, Wi-Fi, a shared swimming pool, and on-site parking.

Best family friendly Pienza villas and holiday home

Among the 19 accommodations in Pienza, here are the 4 best family friendly villas and holiday homes

Borgo Sant'ambrogio - Resort - Pienza
9.0 1551 reviews

Borgo Sant'ambrogio - Resort

farm, Trequanda
Borgo Sant'Ambrogio - Resort is located in the Tuscan countryside near Pienza, a short drive from Siena and Arezzo, offering stunning views of the Val d'Orcia. The resort has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The resort features a traditional Tuscan design with a garden and barbecue facilities. Guests can enjoy a seasonal outdoor pool, a restaurant, a bar, a fitness centre and free Wi-Fi, as well as bike and car hire for exploring the surrounding countryside.
Brunhouse - Pienza
9.1 31 reviews

Brunhouse

house, San Quirico d'Orcia
Brunhouse is located in a peaceful setting just 5km from the charming spa town of Bagno Vignoni, 40km from Mount Amiata and 45km from Piazza del Campo in Siena. The property has received excellent ratings for its location, cleanliness and overall experience.
This 2-bedroom house, spanning 100 square metres, comfortably accommodates up to 4 guests. Guests can enjoy panoramic city views from the private balcony, relax in the garden, or prepare meals in the fully equipped kitchen.
Locanda In Tuscany - Pienza
9.4 81 reviews

Locanda In Tuscany

farm, Castiglione d'Orcia
The Locanda in Tuscany is a rural retreat situated just 3.1 miles from the charming town of Castiglione d'Orcia and 16 miles from the historic Montepulciano, making it an ideal base for exploring the beautiful Tuscan countryside. This farm stay consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers a range of accommodation options, each featuring charming wood-beamed ceilings and a choice of bed linens. Guests can enjoy the on-site restaurant, relax by the outdoor pool and garden, or participate in activities like cooking classes, horse riding, and mushroom picking.
Villa Poggio Castagni Tra Pienza E Montepulciano - Pienza
10 16 reviews

Villa Poggio Castagni Tra Pienza E Montepulciano

house, Torrita di Siena
This luxury villa, located in the Val d'Orcia between Pienza and Montepulciano, offers panoramic views of Pienza, Montalcino, Radicofani, and Monte Amiata, with the nearest village, Torrita di Siena, approximately 6 kilometres away.
This 5-bedroom, 5-bathroom property sleeps 10 guests and features a private infinity pool, a professional kitchen, a gym, an outdoor fireplace, and barbecue area, all within a renovated farmhouse boasting ancient and modern styles.

Frequently asked questions about villa rentals in Pienza

  • What is the best time to visit Pienza?

    Spring and autumn are the most pleasant times to visit Pienza, with mild temperatures and fewer crowds. The countryside is particularly stunning in the spring, when the wildflowers are in bloom. If you're a foodie, you might want to visit in the autumn, when the local harvest festivals take place.
  • What are the best villa rentals in Pienza?

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

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

    The shoulder seasons, April-May and September-October, are generally the best time to book a villa rental in Pienza. You'll find more availability and often better rates than during the peak summer months. If you're planning a trip during the summer, it's best to book your villa well in advance.
  • What are the best villa rentals with a pool in Pienza?

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

  • What are the top hiking trails near Pienza?

    There are some lovely hiking trails in the Val d'Orcia. The Sentiero del Cassia is a great option for a moderate hike, offering stunning views of the rolling hills and vineyards. For a more challenging hike, try the Sentiero del Monte Amiata, which takes you to the summit of Mount Amiata, the highest peak in the area.
  • What are the best villa rentals with a jacuzzi in Pienza?

    The best villa rentals with a jacuzzi in Pienza are Agriturismo Il Macchione, Poggio Ai Gelsi and Villa I Cipressini Piscina Riscaldata Spa Toscana.

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

    Renting a villa in Pienza offers a great deal of privacy and flexibility. You can enjoy your own space, cook your own meals, and explore the area at your own pace. Many villas also offer stunning views of the surrounding countryside, making them the perfect place to relax and unwind.
  • What are the best villa rentals for families and kids in Pienza?

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

  • Are there popular destinations near Pienza?

    Absolutely! Pienza is ideally located for exploring the beautiful region of Tuscany. Nearby destinations include the charming hilltop town of Montepulciano, known for its excellent wine, and the historic city of Siena, famous for its Palio horse race. You can also easily reach the picturesque towns of San Quirico d'Orcia and Montalcino, both of which are renowned for their wine production.
  • What are the best pet friendly villa rentals in Pienza?

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

  • What are the best villa rentals with parking in Pienza?

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

Popular destinations

Best Pienza villas and holiday homes with parking

Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking - Pienza
9.7 70 reviews

Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking

house, Montepulciano
Villa Fè is situated in the Tuscan countryside, just 7.4 kilometres from the charming town of Montepulciano and 4.6 kilometres from the thermal baths of Montepulciano Terme. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The villa is a spacious three-bedroom property, covering 90 square metres. Enjoy a range of amenities including a private pool, hot tub, fitness centre, and a fully equipped kitchen, perfect for relaxing and exploring the beautiful Tuscan region.
Agriturismo Poggio Tobruk - Pienza
9.5 599 reviews

Agriturismo Poggio Tobruk

farm, Pienza
Agriturismo Poggio Tobruk is situated in the Val d'Orcia Park, a UNESCO World Heritage Site, just 10 kilometres from the historic town of Pienza, offering stunning views of the olive groves and Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers self-catering apartments with a fully equipped kitchenette, a spacious dining room for enjoying traditional Tuscan cuisine, and a terrace or balcony for relaxing. Guests can enjoy a range of amenities including a tennis court, a garden, and free parking, as well as purchase authentic olive oil produced directly on the farm.
Villa "Podere Spagliarda" With Private Pool, Terrace & Wi-fi - Pienza
No reviews

Villa "Podere Spagliarda" With Private Pool, Terrace & Wi-fi

house, San Quirico d'Orcia
This four-bedroom, four-bathroom farmhouse, sleeping up to twelve guests, is situated in San Quirico d'Orcia, within 5km of Piazza delle Sorgenti, Pieve di Corsignano, and Tenuta Sanone, and 10km from the Artemisia Gallery and Enoteca Di Ghino.
The 140 square metre property boasts a swimming pool, garden, parking, and a fully equipped kitchen with fridge and dishwasher; barbecue facilities are also available for guests to enjoy.
50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.4 21 reviews

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Castiglione d'Orcia
Farm rental for 5 guests with an excellent rating of 94% based on 21 reviews. You will be located in Castiglione d'Orcia.
Facilities and services include a tennis court, air conditioning and a barbecue. A jacuzzi is available in this accommodation in Castiglione d'Orcia!

Best Pienza villas and holiday homes with a garden

Podere Travagliola - Pienza
9.9 20 reviews

Podere Travagliola

farm, Castiglione d'Orcia
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.
156 M² Villa ∙ 3 Schlafzimmer ∙ 6 Gäste - Pienza
No reviews

156 M² Villa ∙ 3 Schlafzimmer ∙ 6 Gäste

house, Trequanda
House to rent for up to 6 guests. You will be based in Trequanda.
Facilities and services include rooms suitable for events, free parking and an iron. This house in Trequanda 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.
Palazzo Massaini - Cavarciano - Pienza
9.3 994 reviews

Palazzo Massaini - Cavarciano

farm, Pienza
Palazzo Massaini - Cavarciano is located in the Tuscan countryside, 5 kilometres from the charming town of Pienza, close to the San Biagio Church and 18 kilometres from Chianciano Terme. This farm stay has consistently received excellent ratings for its location, cleanliness and overall experience.
The farm offers a variety of accommodation options, including rooms and apartments, to suit different needs and group sizes. Guests can enjoy a delicious Italian breakfast, relax by the swimming pool at a nearby partner property, and benefit from amenities such as free parking, Wi-Fi and air conditioning.
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