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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

Villa Meravigliosa - Six Bedroom Villa, Sleeps 12 - Pienza
No reviews

Villa Meravigliosa - Six Bedroom Villa, Sleeps 12

house, Pienza
This 19th-century Tuscan farmhouse is located in the Val d'Orcia, just a 4-minute drive from Pienza, one of Tuscany's most notable towns, and offers spectacular views of the rolling hills.
This restored villa spans 350 square metres, featuring 6 bedrooms and 6 bathrooms to accommodate up to 12 guests, with amenities including air conditioning, WiFi, a swimming pool, and parking, making it ideal for family reunions or groups exploring the local area such as the Artemisia Art Gallery and Leonini Gardens.
Villa Tiberini Wine Relais - Pienza
9.6 17 reviews

Villa Tiberini Wine Relais

farm, Torrita di Siena
Villa Tiberini Wine Relais, situated in Osteria Delle Noci, is 46 kilometres from Piazza Grande and 17 kilometres from the Terme di Montepulciano.
This farm stay offers satellite TV, a fully equipped kitchen, free Wi-Fi, private parking, an outdoor swimming pool, and a garden with barbecue facilities, with Montepulciano Thermal Baths a 17-kilometre drive away.
Casa Moscatella: A Characteristic Three-story Age-old Farm House Surrounded By Vineyards And Olive Groves, With Free Wi-fi. - Pienza
9.4 50 reviews

Casa Moscatella: A Characteristic Three-story Age-old Farm House Surrounded By Vineyards And Olive Groves, With Free Wi-fi.

house, Montepulciano
This house is located in Montepulciano, just a couple of kilometres from the Val di Chiana and the Church of St. Agnes, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for location and user experience, with an "OK" rating for cleanliness.
The house is a spacious 250 square metre property with three bedrooms, comfortably accommodating up to six guests. This house offers a private pool, a spa tub, a garden, a terrace, and a fully equipped kitchen, as well as free Wi-Fi and parking.
Agriturismo Sant'ansano - Pienza
9.5 117 reviews

Agriturismo Sant'ansano

farm, Castiglione d'Orcia
Agriturismo Sant'Ansano is a farmhouse stay in Castiglione d’Orcia, Tuscany, located 9.2km from Bagno Vignoni and 30.6km from Mount Amiata.
This air-conditioned property offers a swimming pool, garden, free Wi-Fi, and barbecue facilities, along with a kitchen equipped with a fridge, microwave, and dishwasher; pets are welcome.

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

Agriturismo Belagaggio - Pienza
9.5 523 reviews

Agriturismo Belagaggio

farm, Torrita di Siena
Agriturismo Belagaggio is located in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering stunning views of the surrounding countryside. The property has received excellent ratings for its location, cleanliness and overall experience.
This recently renovated farmhouse offers comfortable accommodation with a range of amenities including a swimming pool, jacuzzi, and terrace. Guests can enjoy a restaurant serving local cuisine, a spa, and a variety of activities such as cycling and hiking.
Monastero Sant'anna In Camprena - Pienza
9.6 405 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.
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.
House ∙ 2 Bedrooms ∙ 5 Guests - Pienza
No reviews

House ∙ 2 Bedrooms ∙ 5 Guests

house, Montepulciano
Holiday house for up to 5 people. Your accommodation will be located in Montepulciano.
Facilities and services: free parking, a washing machine and a fridge. This house also has a garden!

Frequently asked questions about villa rentals in Pienza

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

    Pienza is a gem! You absolutely must visit the Duomo, a stunning example of Renaissance architecture. Take a stroll through the Piazza Pio II, the heart of the town, and enjoy the views from the Palazzo Piccolomini. If you're looking to explore the surrounding area, the Val d'Orcia is a must-see, with rolling hills and charming villages like Montepulciano and Montalcino.
  • 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.

  • 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, including red deer, wild boar, and foxes. You might also spot birds of prey like buzzards and kestrels. Keep an eye out for the occasional hare or badger too.
  • 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 is the best time to visit Pienza?

    Spring (April-May) and autumn (September-October) are the ideal times to visit Pienza. The weather is mild, the crowds are smaller, and the landscape is at its most vibrant. You can enjoy the fresh air and the beautiful colours of the changing seasons.
  • 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.

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

    To get the best deals and availability, book your villa rental in Pienza a few months in advance, especially if you're travelling during the peak season (June-August). You'll find more flexibility and better prices if you book outside of the summer months.
  • 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.

  • What are the top hiking trails near Pienza?

    There are several great hiking trails near Pienza. The Sentiero del Bruco, a circular trail around the town, offers stunning views of the Val d'Orcia. The Sentiero della Via Francigena, a historic pilgrimage route, takes you through picturesque countryside and charming villages.
  • 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 advantages of renting a house or a villa in Pienza

    Renting a villa in Pienza gives you the privacy and flexibility to enjoy your holiday at your own pace. You can cook your own meals, relax in your own space, and enjoy the peace and quiet of the Tuscan countryside. It's a great way to experience the local culture and immerse yourself in the Italian way of life.
  • 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.

  • Are there popular destinations near Pienza?

    Absolutely! Pienza is ideally located for exploring other Tuscan gems. You can easily visit Montepulciano, known for its Vino Nobile wine, or Montalcino, famous for its Brunello di Montalcino. Siena, a medieval city with a beautiful historic centre, is also within easy reach.

Popular destinations

Best Pienza villas and holiday homes with parking

Casa Primavera A Rocca D'orcia - Pienza
9.6 73 reviews

Casa Primavera A Rocca D'orcia

house, Castiglione d'Orcia
Casa Primavera is situated in the peaceful village of Rocca d'Orcia, just 5km from Castiglione d'Orcia, making it a great base for exploring the beautiful Val d'Orcia region and its natural wonders like Bagno Vignoni (5km) and Bagno San Filippo (18km). The property has received excellent ratings for its location, cleanliness, and overall experience.
Casa Primavera offers 75 square metres of space, with two bedrooms and one bathroom, comfortably accommodating up to four guests. The self-catering holiday home features a fully equipped kitchen, a relaxing living room, free Wi-Fi, parking, and a peaceful location, perfect for a relaxing getaway.
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.
Civico 176 - Pienza
9.5 26 reviews

Civico 176

house, Chianciano Terme
This holiday home in Chianciano Terme is conveniently located a short drive (5.5km) from Montepulciano Terme, 24km from Bagno Vignoni, and 24km from Bagni San Filippo, offering easy access to these popular thermal spa towns.
The 125 square metre property boasts two bedrooms, two bathrooms, and sleeps up to 11 guests, featuring a fully equipped kitchen with dishwasher, air conditioning, Wi-Fi, and private parking; a washing machine is also provided.
Podere San Bono - Pienza
9.4 19 reviews

Podere San Bono

house, Montepulciano
Podere San Bono is situated in the Tuscan countryside, just 88 kilometres from Florence Airport, offering a peaceful escape from the bustling town of Montepulciano. This property has received excellent ratings for location, cleanliness, and overall user experience.
The villa boasts five bedrooms and covers 140 square metres, providing ample space for families or groups. Guests can enjoy a private pool, a fully equipped kitchen, a spacious balcony, a garden, barbecue facilities, and free parking.

Best Pienza villas and holiday homes with a garden

La Chiusa Dei Monaci - Pienza
9.1 176 reviews

La Chiusa Dei Monaci

farm, Trequanda
La Chiusa dei Monaci is a farm stay located in Castelmuzio, a small village near Trequanda, just 50 km from both Siena and Arezzo, offering a peaceful escape from the hustle and bustle. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The farm stay offers a 40 square metre, one-bedroom apartment with a fully equipped kitchen, perfect for a family of four. Guests can enjoy the private terrace with stunning views, the garden, and barbecue facilities for al fresco dining.
156 M² Villa ∙ 3 Schlafzimmer ∙ 6 Gäste - Pienza
No reviews

156 M² Villa ∙ 3 Schlafzimmer ∙ 6 Gäste

house, Trequanda
House rental for up to 6 guests. You will be based in Trequanda.
Facilities and services include free parking, a fridge and a garden. This house also has a terrace!
Antico Podere La Martinella- Ground Floor Apartment - Pienza
9.7 238 reviews

Antico Podere La Martinella- Ground Floor Apartment

apartment, San Quirico d'Orcia
This San Quirico d'Orcia farmhouse offers a peaceful stay, a 15-minute walk from Palazzo Chigi, the Collegiate Church of San Quirico, and Horti Leonini, with the Chapel of Our Lady of Vitaleta and Poggio Grande within 5km.
The self-catering property features a terrace, garden, parking, Wi-Fi, and allows pets; housekeeping is provided once per stay.
Apartment In A Hotel "Villa Cielo" With Shared Pool, Private Terrace & Wi-fi - Pienza
No reviews

Apartment In A Hotel "Villa Cielo" With Shared Pool, Private Terrace & Wi-fi

house, Trequanda
This 156 square meter, 3-bedroom, 2-bathroom villa apartment, accommodating up to 6 guests, is located within the 'Villa Cielo' hotel in Trequanda, offering a resort-like atmosphere and convenient access to local cultural landmarks such as the Artemisia Gallery and Palazzo Borgia, with Florence and Siena approximately 60 kilometers and 40 kilometers away respectively. Guests can enjoy a shared seasonal swimming pool (April to November), a private terrace and balcony, air conditioning, internet, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, and 2 dedicated parking spaces, with pets allowed for a fee and a baby cot available.
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