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Pienza holiday homes
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12 Villa rentals in Pienza

Best Pienza villas and holiday homes with a pool

Among the 8 accommodations in Pienza, here are the 4 best villas and holiday homes with a pool

Villa Lauretana By Posarellivillas - Pienza
8.0 2 reviews
Pienza
18/08 – 22/08
NZ$1752/nighttotal: NZ$7008 (4 )

Villa Lauretana By Posarellivillas

6 4
house , Torrita di Siena
Villa Lauretana, near Torrita di Siena, is conveniently located approximately 15km from Montepulciano Terme, 32km from Bagno Vignoni, and 45km from Piazza Grande in Tuscany.
This spacious 700 square metre villa boasts six bedrooms, four bathrooms, and accommodates up to 22 guests, offering a private pool, extensive garden, terrace, free Wi-Fi, and parking; nearby activities include exploring the historical towns of Montepulciano Terme, Bagno Vignoni, and Piazza Grande.
Agriturismo Ardene - Pienza
9.2 61 reviews
Pienza
18/08 – 22/08
NZ$4746/nighttotal: NZ$18984 (4 )

Agriturismo Ardene

6 4
farm , Montepulciano
Agriturismo Ardene is located just outside Montepulciano, a short drive from the historic centre and surrounded by olive groves. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The farm offers various accommodation options, including suites and apartments, all with terracotta floors and some featuring fireplaces or wood-beamed ceilings. You can enjoy a range of amenities including a swimming pool, a spa, a restaurant, a bar, and tennis courts, all set within a peaceful and relaxing atmosphere.
Poggio Ai Gelsi - Pienza
9.3 593 reviews
Pienza
07/12 – 10/12
NZ$920/nighttotal: NZ$2760 (3 )

Poggio Ai Gelsi

4 8
house , Pienza
Poggio ai Gelsi is a holiday home located in Pienza, just 40km from Siena, offering stunning views of the Val d'Orcia. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features private bathrooms, air conditioning, comfortable bedding, and a kitchen equipped with a fridge, microwave, and dishwasher. Guests can enjoy the private pool, terrace, garden, and parking, as well as the nearby attractions of Pienza's historic centre.
Agriturismo Selvoli - La Scuola - Pienza
9.8 65 reviews
Pienza
09/10 – 12/10
NZ$249/nighttotal: NZ$747 (3 )

Agriturismo Selvoli - La Scuola

1 2
cabin , Pienza
This pet-friendly studio apartment, a former schoolhouse near Selvoli, is a short distance from Pienza.
The self-contained property offers a well-equipped kitchenette, bathroom with shower, a French-size bed (190x160cm), private garden, and sleeps two, ideal for couples seeking a peaceful base to explore Pienza.

Best family friendly Pienza villas and holiday home

Among the 8 accommodations in Pienza, here are the 4 best family friendly villas and holiday homes

80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Pienza
9.8 47 reviews
Pienza
30/09 – 03/10
NZ$378/nighttotal: NZ$1134 (3 )

80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 4
farm , Pienza
Farm listing for up to 4 people with an excellent rating of 98% based on 47 reviews. You will be located in Pienza.
Services and facilities: a terrace, a swimming pool and a barbecue.
La Casa Di Vignoni Alto - Pienza
8.5 61 reviews
Pienza
19/08 – 22/08
NZ$504/nighttotal: NZ$1512 (3 )

La Casa Di Vignoni Alto

2 4
house , San Quirico d'Orcia
La Casa di Vignoni Alto is a holiday home located in the village of Bagno Vignoni, 1.9 kilometres from the famous thermal baths and a short drive from other attractions such as Bagni San Filippo (19 kilometres) and Montepulciano Terme (29 kilometres).
The 250 square metre property features two bedrooms, two bathrooms, and can accommodate up to nine guests, and offers amenities such as a fully equipped kitchen, a garden, a tennis court, and free Wi-Fi.
A Casa Di Gabri - Pienza
9.3 10 reviews
Pienza
13/07 – 15/07
NZ$298/nighttotal: NZ$596 (2 )

A Casa Di Gabri

3 2
house , Torrita di Siena
This charming holiday home is located in Montefollonico, a peaceful village just a short drive from Torrita di Siena, offering easy access to the town's shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house provides ample space for up to five guests, with three bedrooms, two bathrooms, and a total floor area of 100 square metres. Guests can enjoy a fully equipped kitchen, a relaxing garden, and a terrace for outdoor dining, as well as free Wi-Fi access throughout the property.
Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
Pienza
30/09 – 03/10
NZ$480/nighttotal: NZ$1440 (3 )

Villa Basilico - Cignella Resort Chalet In Tuscany

2 4
chalet , Trequanda
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.

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.

Destinations nearby

Best Pienza villas and holiday homes with parking

Agriturismo Zampugna - Pienza
9.4 631 reviews
Pienza
24/07 – 27/07
NZ$1329/nighttotal: NZ$3987 (3 )

Agriturismo Zampugna

2 3
farm , Trequanda
Agriturismo Zampugna is situated in Montefollonico, a charming village just a short drive from Trequanda and approximately 52 miles from Perugia San Francesco d'Assisi Airport. The farm stay has received excellent ratings for its location, cleanliness and overall user experience.
The property offers a peaceful garden and a private entrance for a relaxing stay. Guests can enjoy a swimming pool with stunning views, a terrace, barbecue facilities, a picnic area, a restaurant and free parking.
La Chiusa Dei Monaci - Pienza
9.1 180 reviews
Pienza
28/07 – 31/07
NZ$492/nighttotal: NZ$1476 (3 )

La Chiusa Dei Monaci

2 5
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.
Primo Maggio - Pienza
10 2 reviews
Pienza
27/06 – 28/06
NZ$805/nightfor 1 night

Primo Maggio

1 4
house , Castiglione d'Orcia
Primo Maggio is a detached house in Castiglione d'Orcia, located 5.3 kilometres from Bagno Vignoni and 17.7 kilometres from Bagni San Filippo, with Mount Amiata 30.6 kilometres away.
This property offers 180 square metres of living space with one bedroom, four bathrooms, and can accommodate up to 15 guests, featuring complimentary WiFi and a fully equipped kitchen.
Agriturismo Le Macchie - Pienza
9.8 122 reviews
Pienza
30/09 – 03/10
NZ$781/nighttotal: NZ$2343 (3 )

Agriturismo Le Macchie

3 4
farm , Pienza
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.

Best Pienza villas and holiday homes with a garden

Agriturismo Renello - Pienza
9.0 117 reviews
Pienza
29/06 – 02/07
NZ$575/nighttotal: NZ$1725 (3 )

Agriturismo Renello

1 3
house , Torrita di Siena
Agriturismo Renello is located in Petroio, in the Tuscan countryside, 15km from Montepulciano and a 45-minute drive from Lake Trasimeno, offering a peaceful retreat amongst rolling hills. This property has received excellent user and location ratings, as well as a very good cleanliness rating.
This rural retreat offers comfortable rooms with seating areas and en suite bathrooms. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden with BBQ facilities, a restaurant serving regional cuisine, a fitness center, a tennis court, and free Wi-Fi, parking, and bike rentals.
Agriturismo La Creta - Pienza
9.8 26 reviews
Pienza
19/07 – 23/07
NZ$249/nighttotal: NZ$996 (4 )

Agriturismo La Creta

1 2
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.
Zampugna Estate - Spigo's Cottage - Pienza
10 1 review
Pienza
02/07 – 03/07
NZ$949/nightfor 1 night

Zampugna Estate - Spigo's Cottage

1 2
cottage , Torrita di Siena
This Torrita di Siena holiday cottage is located near the Val di Chiana, approximately 10km from the Triacca Winery and Pienza's historic centre.
The 70 square metre property sleeps two, boasting a private garden, barbecue, fireplace, fully equipped kitchen with washing machine, balcony, swimming pool, and Wi-Fi; ideal for exploring the Tuscan countryside.
Le Sorbelle D'orcia - Pienza
9.5 129 reviews
Pienza
10/10 – 12/10
NZ$918/nighttotal: NZ$1836 (2 )

Le Sorbelle D'orcia

2 5
farm , Pienza
Agriturismo Le Sorbelle d'Orcia, near Pienza in Tuscany, is conveniently located 19 kilometres from Montepulciano Terme, 21 kilometres from Bagni San Filippo, and 4.3 kilometres from Bagno Vignoni, offering easy access to these popular towns.
This one-bedroom, one-bathroom rural retreat sleeps three guests and boasts a swimming pool, free private parking, and a varied breakfast; bachelor/hen parties are not permitted.
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