Search Pienza villas and holiday homes

12 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Pienza villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Lupaia - Pienza
9.8 332 reviews
Pienza
27/06 – 28/06
A$3699/nightfor 1 night

Lupaia

2 4
farm , Torrita di Siena
Lupaia is a converted farmhouse located on a hilltop overlooking Montepulciano, just 10km from Torrita di Siena, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
This charming rural retreat features 12 individually designed rooms, each with a private terrace or garden. Guests can enjoy a range of amenities, including a swimming pool, spa, restaurant, and fitness centre, as well as participate in cooking classes and cheese tasting events.
Agriturismo I Savelli - Pienza
9.3 77 reviews
Pienza
18/08 – 22/08
A$599/nighttotal: A$2396 (4 )

Agriturismo I Savelli

2 4
farm , Castiglione d'Orcia
Agriturismo I Savelli, a farmhouse in Castiglione d’Orcia, Tuscany, is situated 8.2km from Bagno Vignoni and 12.2km from Bagni San Filippo, offering easy access to the thermal baths and the Montepulciano wine region.
This self-catering property boasts a swimming pool with stunning garden views, a terrace, free Wi-Fi, and private parking; some units include air conditioning and fully equipped kitchens.
Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
8.0 1 review
Pienza
19/06 – 20/06
A$389/nightfor 1 night

Villa Basilico - Cignella Resort Chalet In Tuscany

2 2
chalet , Trequanda
This Trequanda holiday home is located in Osteria Delle Noci, 46 kilometres from Piazza Grande and 17 kilometres from Montepulciano Terme.
This two-bedroom, two-bathroom chalet offers 93 square metres of living space for up to seven guests, featuring air conditioning, a dishwasher, a microwave, and access to a communal swimming pool at Villa Basilico - Cignella Resort.
80 M² House ∙ 2 Bedrooms ∙ 3 Guests - Pienza
Pienza
06/09 – 08/09
A$460/nighttotal: A$920 (2 )

80 M² House ∙ 2 Bedrooms ∙ 3 Guests

2 2
house , Trequanda
This holiday cottage is located in a tranquil Tuscan setting, a short 500-meter walk from a communal swimming pool and within easy reach of Pienza and Montepulciano.
This 80 square meter holiday home accommodates up to three guests in two bedrooms and features a kitchen with a fridge, freezer, and dishwasher, air conditioning, and a terrace or balcony, with opportunities for hiking in Val d'Orcia and visiting thermal springs in Bagno Vignoni.

Best family friendly Pienza villas and holiday homes

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

Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
Pienza
19/06 – 20/06
A$389/nightfor 1 night

Villa Basilico - Cignella Resort Chalet In Tuscany

2 2
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.
Villa Pianoia  Elegance And Historic Charm For Groups And Special Events - Pienza
Pienza
13/08 – 17/08
A$4329/nighttotal: A$17316 (4 )

Villa Pianoia Elegance And Historic Charm For Groups And Special Events

7 6
house , Montepulciano
Villa Pianoia, a large holiday home in the Tuscan countryside between Montepulciano and the Val d'Orcia, offers easy access to attractions such as the Piscine Termali Theia and Terme di Chianciano.
This 450-square-metre, two-level property boasts seven bedrooms, nine bathrooms, and accommodates up to sixteen guests, featuring two living rooms with fireplaces, two dining areas with fully equipped kitchens, a mini pool with a whirlpool, and an Italian garden.
Agriturismo Marinello - Pienza
9.5 1297 reviews
Pienza
13/09 – 16/09
A$266/nighttotal: A$798 (3 )

Agriturismo Marinello

1 1
farm , Pienza
Agriturismo Marinello is located in the Val d’Orcia, a UNESCO World Heritage Site, just 4km from the centre of Pienza and a 32km drive from Montalcino. The farm has received excellent ratings for location, cleanliness and overall experience.
The farm offers both rooms and apartments, all with traditional Tuscan features, like wood-beamed ceilings and wrought-iron beds. Guests can enjoy a private garden, a swimming pool open from May to September, and a fully equipped kitchen.
Villa Cielo- Cignella Resort Tuscany Accommodation - Pienza
Pienza
10/10 – 12/10
A$482/nighttotal: A$964 (2 )

Villa Cielo- Cignella Resort Tuscany Accommodation

3 5
house , Trequanda
This spacious 160 square meter villa, located in Trequanda, offers panoramic views of the Tuscan hills and is situated within the Cignella Resort, providing convenient access to local attractions such as the Artemisia Gallery and Palazzo Borgia. This family-friendly property accommodates up to six guests across three bedrooms, features a fully equipped kitchen with a dishwasher and washing machine, air conditioning, Wi-Fi, and access to resort common areas including a swimming pool and gardens, with parking available.

Frequently asked questions about villa rentals in Pienza

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

    You absolutely must visit the Duomo, a stunning example of Renaissance architecture. The panoramic views from the top of the hill are incredible, especially from the Piazza Pio II. For a taste of the local history, head to the Museo Diocesano, housed in a former monastery. And if you're looking for a day trip, the charming medieval town of Montepulciano is just a short drive away.
  • 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, where Pienza sits, is home to a variety of wildlife. You might spot red deer, wild boar, and even the occasional fox in the surrounding hills. The area is also known for its birdlife, with species like the kestrel and the hoopoe often seen soaring overhead.
  • 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 pleasant, the crowds are smaller, and the landscape is at its most vibrant. You can enjoy the outdoors without the scorching summer heat or the chilly winter temperatures.
  • 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?

    Booking a villa rental in Pienza during the shoulder seasons, like spring or autumn, is generally easier. You'll have a wider selection and potentially better prices. However, if you're looking for a summer getaway, it's best to book well in advance, especially if you have a large group.
  • 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?

    The Sentiero del Cassia is a popular hiking trail that runs through the Val d'Orcia, offering stunning views of the rolling hills and vineyards. The trail starts in the village of San Quirico d'Orcia and leads to Pienza. Another great option is the Sentiero della Via Francigena, which follows the ancient pilgrimage route through the region.
  • 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 offers a great deal of privacy and independence. You can enjoy your own space, cook your own meals, and relax at your own pace. It's also a great option for families or groups of friends who want to spend quality time together.
  • 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! Siena, with its iconic Piazza del Campo, is a must-see, just a short drive away. The charming town of Montepulciano, known for its Vino Nobile, is also within easy reach. For a taste of Etruscan history, head to the archaeological site of Chiusi, about 30 km from Pienza.

Destinations nearby

Best Pienza villas and holiday homes with parking

Agriturismo Pescaia - Pienza
9.7 814 reviews
Pienza
18/06 – 20/06
A$204/nighttotal: A$408 (2 )

Agriturismo Pescaia

2 2
farm , Montepulciano
Agriturismo Pescaia is situated in Montepulciano, a short drive from Chianciano Terme and San Quirico d’Orcia, offering a peaceful retreat in the Tuscan countryside. This farm stay consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartments are decorated in a rustic style, providing a comfortable and authentic Tuscan feel. Guests can enjoy amenities such as a fully equipped kitchen, free Wi-Fi, and a private bathroom, as well as interact with farm animals and indulge in fresh produce grown on-site.
160 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Pienza
Pienza
10/10 – 12/10
A$471/nighttotal: A$942 (2 )

160 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

3 5
house , Trequanda
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.
Casa Remolina - Pienza
9.7 38 reviews
Pienza
03/08 – 08/08
A$223/nighttotal: A$1115 (5 )

Casa Remolina

2 2
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.
600 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
Pienza
07/12 – 10/12
A$702/nighttotal: A$2106 (3 )

600 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

4 8
house , Pienza
This elegant manor house and cosy cottage offer a tranquil retreat just outside Pienza's historic centre, within a 1.5 kilometre drive or pleasant walk to Piazza Pio II and the Cathedral, placing you on the doorstep of the Val d'Orcia's UNESCO World Heritage landscapes. Accommodating up to eight guests, this property spans 600 square meters and features four bedrooms, including three en-suite doubles in the manor house, a further en-suite double in the cottage with a kitchenette, and air conditioning throughout, alongside a garden, terrace, and parking.

Best Pienza villas and holiday homes with a garden

Well-equipped Holiday Home In Spedaletto Italy With Private Pool - Pienza
10 2 reviews
Pienza
10/10 – 12/10
A$848/nighttotal: A$1696 (2 )

Well-equipped Holiday Home In Spedaletto Italy With Private Pool

4 5
house , Pienza
This charming holiday home is located in Ospedaletto, a peaceful district just 4.2 kilometres from Bagno Vignoni and 19 kilometres from Montepulciano Terme, making it an ideal base for exploring the beautiful Tuscan countryside. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The spacious 4-bedroom villa, with a floor area of 130 square metres, comfortably accommodates 8 guests. Enjoy a refreshing dip in the private pool, relax in the garden, and explore the surrounding area on complimentary bicycles.
Nice Apartment With A/c, Wifi, Pool, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano - Pienza
Pienza
19/06 – 21/06
A$424/nighttotal: A$848 (2 )

Nice Apartment With A/c, Wifi, Pool, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano

2 2
farm , Trequanda
This Trequanda farm stay is situated in the Orcia Valley, 10 kilometres from Torrita di Siena and 16 kilometres from Montepulciano, offering views of the surrounding hills and a nearby lake.
This 92 square metre farmhouse accommodates up to four guests in two bedrooms and two bathrooms, featuring a fully-equipped kitchen, air conditioning, a terrace, a shared swimming pool open from April to November, and is accessible for guests with disabilities.
Agriturismo La Creta - Pienza
9.8 26 reviews
Pienza
19/07 – 23/07
A$206/nighttotal: A$824 (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.
My Rental Homes - Villa Monticchiello With Pool And Garden Surrounding The Property - Pienza
Pienza
12/09 – 19/09
A$2124/nighttotal: A$14868 (7 )

My Rental Homes - Villa Monticchiello With Pool And Garden Surrounding The Property

7 2
house , Pienza
Villa Monticchiello, a luxurious farmhouse in the Val d'Orcia, is located 2 km from Monticchiello and 5 km from Pienza, offering easy access to Palazzo Piccolomini and Palazzo Borgia.
This 700 sq m property boasts 7 bedrooms, 8 bathrooms, a private 15m x 5m swimming pool, a fully equipped kitchen, and accommodates up to 14 guests, with amenities including air conditioning, Wi-Fi, and a barbecue area.
©2026 cozycozy.com