Vacation Rentals in Pienza

114 available vacation rental offers

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

114 Holiday rentals and Airbnb in Pienza

Discover Exceptional Family Holiday Rentals in Pienza, Italy

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Pienza, Italy.

Podere Casa Andrei - Pienza
9.3 92 reviews

Podere Casa Andrei

apartment, Pienza
Casa Andrei, a three-bedroom apartment in Pienza, enjoys stunning garden views and is situated 16km from Bagno Vignoni, 18km from Montepulciano Terme, and 26km from Bagni San Filippo.
This self-catering property sleeps nine guests and offers free Wi-Fi, private parking, a fully equipped kitchen with fridge and microwave, and accessibility features for disabled guests.
70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Pienza
10 4 reviews

70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Pienza
Accommodation for 4 people with an excellent rating of 100% based on 4 reviews. You will be in Pienza.
Services and facilities: a garden, a kitchen and free parking. This apartment is ideal for families.
Le Sorbelle D'orcia - Pienza
9.5 149 reviews

Le Sorbelle D'orcia

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.
Casa Valerie - Pienza
9.3 3 reviews

Casa Valerie

house, Trequanda
Casa Valerie is situated in Castelmuzio, a charming village just 14 miles from Bagno Vignoni and 31 miles from Piazza Grande, offering easy access to the region's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom villa, spanning 150 square metres, comfortably accommodates up to four guests. The property features a private pool with mountain views, a spa bath, a fully equipped kitchen, an outdoor fireplace, and a peaceful garden, providing a relaxing and enjoyable stay.

Best Pienza holiday rentals with parking

Montepulcianolettings House - Pienza
10 3 reviews

Montepulcianolettings House

apartment, Montepulciano
This three-bedroom house, perfect for families, is centrally located in Montepulciano's historic centre, offering easy walking access to all major sights.
The property features a fully equipped kitchen, two ensuite bedrooms, and a spacious studio apartment with a double bed and sofa bed, accommodating up to six guests; no lift is present.
Agriturismo Podere San Gregorio - Pienza
9.2 219 reviews

Agriturismo Podere San Gregorio

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.
Holiday Home A Casa Di Gabri By Interhome - Pienza
No reviews

Holiday Home A Casa Di Gabri By Interhome

house, Torrita di Siena
This three-bedroom holiday home, near Montefollonico, is situated 15km from Montepulciano Terme and 24km from Bagno Vignoni, offering easy access to the Tuscan countryside.
The 100 square metre property boasts two bathrooms, a fully equipped kitchen including a dishwasher, private parking, Wi-Fi, and a terrace, comfortably sleeping up to nine guests.
Vento D’orcia - Pienza
9.8 719 reviews

Vento D’orcia

farm, Pienza
Vento d'Orcia, a farm stay located 16 kilometres from Bagno Vignoni and 50 kilometres from Mount Amiata in the Tuscan countryside, offers a peaceful retreat with stunning garden views and a dedicated children's playground.
This family-friendly property features a restaurant serving authentic Tuscan cuisine, a continental breakfast, and room service, as well as air conditioning, a flat-screen TV with streaming services, a safety deposit box, and a private bathroom with a walk-in shower, hairdryer, and complimentary toiletries.

Frequently asked questions about holiday rentals in Pienza

  • What are some interesting places to visit in or near Pienza?

    Pienza is a beautiful town, but you also have a lot to see in the surrounding area. The Duomo di Pienza is a must-see, and the Palazzo Piccolomini is a great place to learn about the history of the town. For a day trip, visit the nearby town of Montepulciano, known for its Vino Nobile wine. If you're interested in art, the Museo Diocesano in Pienza is worth a visit.
  • What are the best Airbnb and holiday rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are among the best Airbnb and holiday rentals in Pienza.

  • Which walking or cycling routes are the best in Pienza?

    Pienza is perfect for exploring on foot. The historic centre is small and easily walkable, and there are plenty of charming alleyways to discover. For a longer walk, try the Sentiero della Val d'Orcia, which offers stunning views of the Tuscan countryside. If you prefer cycling, the Val d'Orcia is also great for a leisurely bike ride, with gentle hills and picturesque landscapes.
  • What are the most popular Airbnbs in Pienza?

    Among the Airbnbs in Pienza, The Cedar House, La Dimora Di Pienza Family 2 Rooms and Panoramic Apaertment Val D'orcia are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Pienza?

    Pienza is a great base for exploring the Val d'Orcia, a UNESCO World Heritage Site. You can go hiking or mountain biking in the surrounding hills, or enjoy a picnic in one of the many vineyards. There are also opportunities for horseback riding and hot air ballooning in the area.
  • What are the best holiday rentals with a pool in Pienza?

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

  • What other towns or cities can be easily accessed from Pienza?

    Pienza is well-connected to other towns and cities in Tuscany. You can easily reach Siena, Florence, and Rome by car or train. For a day trip, visit the charming hilltop town of Montepulciano, just a short drive away. You can also easily reach the beautiful Lake Trasimeno, a popular destination for swimming and watersports.
  • What are the best rentals for families and kids in Pienza?

    The best rentals for families and kids in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo.

  • What amenities are commonly available in vacation rentals in Pienza?

    Most vacation rentals in Pienza offer basic amenities like a kitchen, bathroom, and Wi-Fi. Many also have a private garden or terrace, and some even have a swimming pool. It's always a good idea to check the listing for specific details about the amenities offered.
  • What are the best rentals or Airbnbs with a jacuzzi in Pienza?

    The best holiday rentals or Airbnb with a jacuzzi in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and Poggio Ai Gelsi.

  • What time of year is best to rent a vacation rental Pienza?

    The best time to visit Pienza is in the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be hot and crowded, while winter can be cold and wet. However, if you're looking for a quieter experience, winter can be a good time to visit.

Popular destinations

Discover Holiday Rentals with a Balcony in Pienza, Italy

Watch the local morning bustle with a fresh breeze at holiday rentals featuring an outdoor balcony in Pienza, Italy.

Villa Banditello, Secluded, Panoramic View Over Montepulciano Valley. - Pienza
9.8 113 reviews

Villa Banditello, Secluded, Panoramic View Over Montepulciano Valley.

apartment, Torrita di Siena
This family-friendly holiday home is located in a peaceful rural setting near Torrita di Siena, just a short drive from the historic Church of St Agnes and the Colonna del Marzocco. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and can accommodate up to six guests. Guests can enjoy a range of amenities, including a private garden, swimming pool, tennis court, and a fully equipped kitchen with a dishwasher.
Casa La Rosa Della Val D'orcia - Pienza
No reviews

Casa La Rosa Della Val D'orcia

apartment, San Quirico d'Orcia
Casa La Rosa Della Val D'orcia is a spacious apartment located in San Quirico d'Orcia, offering garden views and a balcony, with Bagno Vignoni 4.7 kilometres away and Mount Amiata 40 kilometres distant.
This residence boasts 3 bedrooms, accommodating up to 11 guests, and features a fully equipped kitchen with a microwave and dishwasher, plus a washing machine, hairdryer, towels, and bed linen, with opportunities for cycling nearby.
L' Antica Oliviera D'orcia - Pienza
9.1 19 reviews

L' Antica Oliviera D'orcia

apartment, San Quirico d'Orcia
This two-bedroom apartment in L'Antica Oliviera D'Orcia is conveniently located in San Quirico d'Orcia, just 5.8 kilometres from the thermal baths of Bagno Vignoni and 22.5 kilometres from Bagni San Filippo.
The 75 square metre property offers a modern kitchen with a fridge, microwave oven, and dishwasher, as well as a terrace, garden, and barbecue facilities, accommodating up to seven guests.
Farmhouse With Pool, Views - Pienza
10 9 reviews

Farmhouse With Pool, Views

farm, Castiglione d'Orcia
This Tuscan farmhouse rental in Castiglione d’Orcia is situated 2.6 km from Val d’Orcia and Terre di Siena, and within 10 km of Tenuta Sanone and Horti Leonini.
The self-catering property boasts a swimming pool, terrace, garden, parking, and barbecue facilities, and is pet-friendly with Wi-Fi.

Compare Pet-Friendly Holiday Rentals in Pienza, Italy

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Pienza, Italy.

Appartamento  Con Giardino Panoramico, Valdorcia - Pienza
9.8 37 reviews

Appartamento Con Giardino Panoramico, Valdorcia

apartment, Torrita di Siena
This charming apartment is situated in a small medieval village between Montepulciano and Pienza, a short distance from the town of Montefollonico, offering a peaceful escape in the heart of Tuscany. It has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers seeking a comfortable and authentic stay.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The apartment features a well-equipped kitchen, air conditioning, a garden with panoramic views, and a fireplace, providing everything you need for a relaxing and enjoyable stay.
38 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Pienza
No reviews

38 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Castiglione d'Orcia
La Cantina Apartment, located within Agriturismo il Noce in Castiglione d'Orcia, Tuscany, is situated 33 kilometres from Mount Amiata and 4 kilometres from Bagno Vignoni, offering proximity to the region's well-known thermal towns.
This 38 square metre self-catering flat accommodates up to three guests, featuring one bedroom and one bathroom, a private kitchen with a fridge, air conditioning, and Wi-Fi, with the added options of on-site wine and olive oil tastings and spa access for an extra fee.
Locanda Di Montisi Piazza Room Between The Hills Of Montalcino - Pienza
No reviews

Locanda Di Montisi Piazza Room Between The Hills Of Montalcino

apartment, Montalcino
This one-bedroom flat is located in the medieval village of Montisi, offering easy access to Siena (approximately 45 kilometres away), Arezzo, Pienza, Montalcino, and Montepulciano, making it an ideal base for exploring the Crete Senesi region.
This pet-friendly accommodation for two includes air conditioning, Wi-Fi, and a workspace, with opportunities for outdoor pursuits such as thermal baths, food and wine tours, and cycling routes readily available.
Agriturismo Le Querciole In Val D'orcia - Pienza
9.6 216 reviews

Agriturismo Le Querciole In Val D'orcia

studio, San Quirico d'Orcia
This studio apartment is located in the Val d'Orcia, just 37 kilometres from Mount Amiata and 48 kilometres from Piazza del Campo in Siena, offering a peaceful escape amidst the rolling hills and vineyards of Tuscany. The studio has received excellent ratings for its cleanliness, location, and overall experience.
The studio features a private entrance, a terrace or balcony, and a garden, providing a relaxing and private space to enjoy the surrounding scenery. Guests can also take advantage of amenities such as a fully equipped kitchen, air conditioning, free Wi-Fi, and parking, allowing for a comfortable and convenient stay.
©2026 cozycozy.com