Compare Vacation Rentals & Airbnb in Pienza

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Pienza vacation rentals
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114 Rentals and Airbnb in Pienza

Best family friendly Pienza vacation rentals

Among the 114 accommodations in Pienza, here are the 4 best family friendly rentals

Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo! - Pienza
10 45 reviews

Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo!

apartment, Pienza
This charming flat is located in the heart of Pienza, just 50 metres from the Duomo and Palazzo Piccolomini, offering easy access to the town's main attractions and the bustling atmosphere of Corso Il Rossellino. The property has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has one bedroom and one bathroom and can comfortably accommodate up to three guests. The well-equipped kitchen features a fridge, freezer, and dishwasher, and the property also benefits from free internet access.
Tuscan Dream Apt With Pool, View & Tennis Court - Pienza
9.8 91 reviews

Tuscan Dream Apt With Pool, View & Tennis Court

apartment, Torrita di Siena
This apartment is located in a renovated monastery in Montefollonico, a charming village in the Tuscan countryside, just 10km from Torrita di Siena. It has received excellent ratings for location, cleanliness, and overall experience.
The property has one bedroom and one bathroom, covering 80 square metres and accommodating up to two guests. Enjoy a range of amenities, including a swimming pool, tennis court, private parking, and a fully equipped kitchen, all set within a beautiful garden.
Il Podere Di Casa Rossa - Pienza - Pienza
9.9 26 reviews

Il Podere Di Casa Rossa - Pienza

apartment, Pienza
This charming farmhouse apartment is situated just outside Pienza, a short walk from the historic town centre, offering easy access to its restaurants, shops and attractions. The property has received excellent ratings for its cleanliness, location and overall experience, making it a popular choice for travellers.
The apartment comprises four suites, comfortably accommodating up to eight guests, providing ample space for families or groups. Guests can enjoy a well-equipped kitchen, a cosy fireplace, a private garden and stunning views of the Val d'Orcia and Mount Amiata.
Villa Falco-cignella Resort Apartments In Tuscany - Pienza
No reviews

Villa Falco-cignella Resort Apartments In Tuscany

house, Trequanda
This villa is located in the exclusive Cignella Resort area of Trequanda, offering panoramic Tuscan countryside views and convenient access to landmarks such as Chiesa di San Francesco and Palazzo Piccolomini.
This 142 square meter property accommodates up to four guests, featuring two double bedrooms, two bathrooms, a fully equipped open-plan living area with a modern kitchen, air conditioning, Wi-Fi, private parking, and access to a shared resort swimming pool.

Best Pienza vacation rentals with parking

La Falegnameria - Pienza
9.6 27 reviews

La Falegnameria

apartment, Castiglione d'Orcia
This one-bedroom apartment in Castiglione d’Orcia offers breathtaking panoramic views of the Val d’Orcia and Mount Amiata, with its precise location providing easy access to the historic centre and local amenities.
Sleeping four guests, the self-catering flat features a kitchen, internet access, and allows pets; enjoy stargazing from its location and explore the Val d’Orcia region with its proximity to local restaurants and attractions.
Casa X2 Con Veranda In Mascagni Farmhouse Pienza - Pienza
No reviews

Casa X2 Con Veranda In Mascagni Farmhouse Pienza

house, Pienza
This restored 16th-century olive oil mill, offering an authentic Renaissance apartment, is situated within the Mascagni Organic Farm, providing immersive Tuscan countryside experiences with unobstructed views of the Val d'Orcia.
This property features 1 bedroom and 1 bathroom, accommodating up to 2 guests, and includes a private veranda, air conditioning, a kitchen with a fridge, freezer, and microwave, as well as a garden and parking.
70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
10 6 reviews

70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Pienza
Agriturismo Il Casato - Il Torchio, a self-catering apartment, is situated 1 kilometre from Pienza's historic centre, offering breathtaking views of the Val d'Orcia and easy access to attractions such as the Vitaleta Chapel (7km), Montepulciano (15km), and Siena (50km).
This 70 square metre property sleeps four, featuring a living room, well-equipped kitchen, one bedroom, one bathroom, and access to a private barbecue area, plus shared garden and terrace; amenities include Wi-Fi, air conditioning, and a washing machine, with optional homemade breakfast and guided winery tours available.
60 M² Apartment ∙ 2 Bedrooms ∙ 3 Guests - Pienza
10 5 reviews

60 M² Apartment ∙ 2 Bedrooms ∙ 3 Guests

apartment, Pienza
Apartment to rent for 3 people with an excellent rating of 100% based on 5 reviews. Your accommodation will be located in Pienza.
Services and facilities: a dish washer, a fridge and an iron.

Frequently Asked Questions about vacation rentals in Pienza

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

    Pienza is a beautiful town, but if you want to explore beyond its charming streets, you should definitely visit the nearby town of Montepulciano. It's known for its wine and has a stunning Duomo. And, of course, you can't miss the stunning views of the Val d'Orcia, just a short drive away. It's a landscape that's been featured in many films, and it's easy to see why.
  • What are the best Airbnb and vacation rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are the most popular Airbnb and vacation rentals in Pienza among travelers.

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

    The best walk in Pienza is around the town walls, offering lovely views of the surrounding countryside. If you're feeling energetic, you can cycle to the nearby town of Monticchiello, which is a short, but scenic, ride. The roads are generally quiet, and you'll be rewarded with breathtaking views.
  • 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 perfect for those who enjoy outdoor activities. You can go hiking in the Val d'Orcia, or try your hand at mountain biking on the trails near the town. There are also plenty of opportunities for horseback riding, and if you're feeling adventurous, you could even try paragliding.
  • What are the best vacation rentals with a pool in Pienza?

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

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

    From Pienza, you can easily reach Siena, a beautiful medieval city, in about an hour by car. You could also visit the charming town of Montalcino, famous for its Brunello wine, or head to the vibrant city of Florence, which is about a two-hour drive.
  • 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 terrace or balcony, offering stunning views of the countryside. Some might even have a swimming pool, especially if you're renting a villa.
  • What are the best rentals or Airbnbs with a jacuzzi in Pienza?

    The best vacation 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?

    Spring and autumn are the best times to visit Pienza, as the weather is pleasant and the crowds are smaller. You'll experience the beauty of the Val d'Orcia in its full glory, with rolling hills and vineyards bathed in golden light. Avoid the summer months if you don't like intense heat.
  • What are the local dishes in Pienza region?

    Pienza is famous for its pecorino cheese, so you must try it in all its forms, from fresh to aged. You should also indulge in the local pasta dishes, like pici cacio e pepe, and the delicious Tuscan bread, known as schiacciata. And don't forget to try the local wines, especially the Rosso di Montalcino.

Popular destinations

Best Pienza vacation rentals with a balcony

Poggiosalto In Toscana - Pienza
9.8 303 reviews

Poggiosalto In Toscana

apartment, Pienza
Podere Poggio Salto is situated in Pienza, just 13 kilometres from the charming town of Bagno Vignoni and 16 kilometres from the renowned wine region of Montepulciano Terme. This apartment has received excellent ratings for location, cleanliness and overall user experience.
This self-catering property offers a comfortable and inviting atmosphere with a private entrance and parking. Guests can enjoy a range of amenities, including a swimming pool with stunning views, a terrace for outdoor dining, a fully equipped kitchen, air conditioning, free Wi-Fi, and a bicycle rental service.
Agriturismo Il Casato Mag-il Giogo - Pienza
9.5 30 reviews

Agriturismo Il Casato Mag-il Giogo

farm, Pienza
Agriturismo il Casato Mag-il Giogo, near Pienza, enjoys a convenient location 8.7km from Bagno Vignoni's thermal springs and 43km from Monte Amiata, offering easy access to Tuscany's renowned hilltop towns.
This 135 square metre property features two bedrooms and two bathrooms, accommodating up to 16 guests, and includes a fully equipped kitchen, terrace, garden, free Wi-Fi, free parking, and table tennis.
Molino Della Tuoma - Pienza
8.6 10 reviews

Molino Della Tuoma

apartment, San Quirico d'Orcia
Molino della Tuoma, a self-catering apartment in San Quirico d’Orcia, enjoys a tranquil setting near the river, 42km from Mount Amiata and 43km from Siena's Piazza del Campo.
This five-guest property boasts a private garden, terrace, jacuzzi, and spa, plus a fully equipped kitchenette, washing machine, and free Wi-Fi and parking.
Chez Anna - Pienza
8.7 9 reviews

Chez Anna

apartment, San Quirico d'Orcia
Chez Anna, a holiday flat in Bagno Vignoni, is located 1.6 kilometres from the town centre and 23 miles from Mount Amiata.
This 120 square metre, two-bedroom holiday flat accommodates up to 11 guests, featuring a fully equipped kitchen, a private terrace, and is a mile from the Bagno Vignoni thermal baths.

Best pet friendly Pienza vacation rentals

Among the 114 accommodations in Pienza, here are the 4 best pet friendly rentals

La Toscana In Terrazza, Montepulciano Centro - Pienza
9.8 230 reviews

La Toscana In Terrazza, Montepulciano Centro

apartment, Montepulciano
This Montepulciano Airbnb, situated in the historic centre, offers easy walking access to Montepulciano's main attractions.
The two-bedroom apartment, sleeping four, boasts a fully equipped kitchen, a private terrace with panoramic views of Lake Trasimeno and the Montepulciano lakes, and parking is available outside the ZTL.
Villa S.anna - Pienza
10 65 reviews

Villa S.anna

house, Montalcino
Villa S.Anna is situated in Montisi, a picturesque village in the Val d'Orcia, approximately 47 kilometres from Siena's Piazza del Campo and 50 kilometres from Arezzo's Piazza Grande.
This 120 square metre, three-bedroom villa offers a private pool, garden, terrace with mountain views, and a well-equipped kitchen, making it an ideal choice for families or groups seeking a relaxing and comfortable stay in the Tuscan countryside.
Villa Pesca Amazing House In The Heart Of Tuscany - Pienza
9.5 2 reviews

Villa Pesca Amazing House In The Heart Of Tuscany

apartment, Trequanda
Villa Pesca, a holiday home in Osteria Delle Noci, Tuscany, is located 47 kilometres from Piazza Grande and 18 kilometres from Montepulciano Terme.
This spacious, air-conditioned apartment offers 156 square metres of living space with 3 bedrooms and 3 bathrooms, accommodating up to 11 guests, and features a fully equipped kitchen, free Wi-Fi, and access to a shared swimming pool.
Casa Bianchini: Ancient Memories - Pienza
No reviews

Casa Bianchini: Ancient Memories

house, Pienza
This restored 1850s property, Casa Bianchini, is located in the historic centre of Monticchiello, within the UNESCO World Heritage Val d'Orcia, 10-15 minutes drive from Pienza.
This two-storey holiday home offers 120 square metres of living space for up to six guests, featuring three bedrooms, two bathrooms, air conditioning, a fully equipped kitchen with a fridge, freezer, and dishwasher, a garden, and internet access, with pets welcome.
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