Tenuta Santo Pietro is a working farm located just three miles from the historic town of Pienza, nestled in the Tuscan countryside. The farm enjoys excellent ratings for its location, cleanliness, and overall experience. The farmhouse dates back to the 13th century and has been beautifully restored, featuring terracotta floors and exposed wooden beams. Guests can enjoy a swimming pool, a restaurant serving traditional Tuscan cuisine, and a range of activities including wine and olive oil tastings, as well as exploring the peaceful gardens.
9.7 463 reviews
Pienza
02/07 – 03/07
A$237/nightfor 1 night
Agriturismo Riposati
2 2
house , Pienza
This house is located near Monticchiello, a charming village just 2 kilometres away, and a short 20-minute drive from the famous town of Montepulciano. It has received excellent ratings for location, cleanliness and user experience. The house has one bathroom and features a fully equipped kitchen, a garden and free Wi-Fi. Guests can enjoy stunning views of the Val d'Orcia hills and relax in the tranquil garden setting.
9.2 272 reviews
Pienza
08/07 – 12/07
A$224/nighttotal: A$896 (4 )
Agriturismo La Buca Di Bellugi
1 2
farm , San Quirico d'Orcia
Agriturismo La Buca di Belluigi is a charming rural retreat just under a mile from San Quirico d'Orcia, a picturesque town in the heart of Tuscany. The property has received excellent ratings for its location, cleanliness, and overall experience. The accommodation features a spacious garden and a swimming pool, perfect for relaxing and enjoying the peaceful surroundings. Guests can also take advantage of a restaurant, free Wi-Fi, and private parking on-site.
Pienza
07/12 – 10/12
A$728/nighttotal: A$2184 (3 )
Maria Gabriella Holiday Home
3 8
house , Pienza
This independent manor house and cottage is located in Monticchiello, offering excellent access to the Val d’Orcia region, with Triacca Winery and La Foce within a few kilometres. The property spans 600 square meters, accommodating up to 8 guests across 4 bedrooms with en suite bathrooms, featuring a fully equipped kitchen, air conditioning, and a furnished outdoor area with a barbecue, with on-site parking and breakfast available on request.
9.8 33 reviews
Pienza
08/08 – 15/08
A$396/nighttotal: A$2772 (7 )
Val D'orcia Deluxe 3 Incantevole Casa Con Vista Sulle Colline, Wifi E Parcheggio
4 5
house , Montalcino
This Montalcino holiday home, situated in San Giovanni d'Asso, is 21km from Bagno Vignoni's thermal springs and 42km from Siena's Piazza del Campo, offering easy access to Val d'Orcia's scenic beauty. The 85-square-metre property features four bedrooms, one bathroom, sleeps thirteen guests, and includes a fully equipped kitchen, private parking, Wi-Fi, a terrace, garden, and stunning views.
9.3 470 reviews
Pienza
26/06 – 29/06
A$342/nighttotal: A$1026 (3 )
Agriturismo Podere San Gregorio
1 4
farm , Pienza
Agriturismo Podere San Gregorio is a restored farmhouse located just a short walk from the centre of Pienza, a charming medieval town in the heart of Tuscany. It is also within easy reach of other popular destinations like Montepulciano and Siena. The property has received excellent ratings for its location, cleanliness and overall experience. The farmhouse offers comfortable accommodation with a private garden and free BBQ facilities. Guests can enjoy a delicious breakfast basket delivered to their room each morning and have the option of purchasing locally produced olive oil and wine.
9.7 176 reviews
Pienza
13/08 – 17/08
A$855/nighttotal: A$3420 (4 )
95 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests
3 6
farm , Pienza
Farm for 7 guests with an excellent rating of 97% based on 176 reviews. This accommodation is based in Pienza. Services and facilities: free parking, a washing machine and a tennis court. This accommodation in Pienza also has a garden!
10 4 reviews
Pienza
13/08 – 17/08
A$849/nighttotal: A$3396 (4 )
Umberto 121
5 6
house , Montalcino
This spacious five-bedroom holiday villa, situated within a historic building in Montalcino, is located 25 kilometres from Piazza Grande, 24 kilometres from Bagno Vignoni, and 26 kilometres from Montepulciano Terme. The property offers 320 square metres of living space, accommodating up to 14 guests with five bedrooms and six bathrooms, and features a garden, shared kitchen, fireplace, free Wi-Fi, and on-site yoga activities.
9.3 128 reviews
Pienza
18/06 – 20/06
A$737/nighttotal: A$1474 (2 )
Locanda In Tuscany
1 2
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.
8.8 304 reviews
Pienza
19/07 – 23/07
A$296/nighttotal: A$1184 (4 )
La Romita Ospitalità Rurale Familiare
1 2
farm , Montalcino
La Romita Ospitalità Rurale Familiare is situated in Montisi, a charming village just a 30-minute drive from Montepulciano, offering a peaceful escape in the Tuscan countryside. The farm has received very good user ratings and excellent ratings for its location and cleanliness. The rural retreat offers a range of country-style rooms with tile or hardwood floors and wrought iron beds. Guests can enjoy a delicious local Tuscan breakfast, relax in the garden with its outdoor seating area, and take advantage of amenities such as laundry facilities and a restaurant serving regional specialties.
9.5 26 reviews
Pienza
17/06 – 22/06
A$161/nighttotal: A$805 (5 )
Il Melograno
2 2
house , Torrita di Siena
Il Melograno is a charming apartment located in Torrita di Siena, a town in the Tuscan countryside, just 53 km from Siena and 43 km from Arezzo. The apartment has received very good user, location and excellent cleanliness ratings. This two-bedroom apartment has one bathroom and offers a terrace with garden views. Guests can enjoy the convenience of a fully equipped kitchen, free parking, and a garden, making it a great choice for families or groups looking for a relaxing and comfortable stay.
9.7 152 reviews
Pienza
09/07 – 19/07
A$306/nighttotal: A$3060 (10 )
Agriturismo Casalpiano
1 3
farm , Pienza
Agriturismo Casalpiano, a family-friendly farmhouse in Pienza, enjoys a convenient location, 12.4km from Montepulciano Terme and 14.3km from Bagno Vignoni, both renowned for their thermal baths, and 45km from Mount Amiata. This self-catering property offers a private entrance, swimming pool, garden, free parking, Wi-Fi, and outdoor play equipment, perfect for families exploring the Tuscan countryside.
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
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.
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.
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.
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
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.
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.
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.
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 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?
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?
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 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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.