Holiday Rentals in Pienza

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Pienza holiday rentals
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114 Holiday Rentals and Airbnb in Pienza

Best family friendly Pienza holiday rentals

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

Via Del Bacio Uno (Literally Kiss Street One) - Pienza
9.9 105 reviews

Via Del Bacio Uno (Literally Kiss Street One)

apartment, Pienza
This recently renovated Pienza apartment is situated on Via del Bacio, centrally located near the Piazza Pio II and the Duomo, offering easy access to Pienza's historical centre.
The 45-square-metre flat features two bedrooms (king-size bed and double sofa bed), sleeping four, a kitchenette with a fridge, and a private bathroom; it's ideal for exploring Pienza's restaurants and shops selling local delicacies such as Pecorino cheese and Pici pasta.
Borgo Sant'ambrogio - Resort - Pienza
9.0 1532 reviews

Borgo Sant'ambrogio - Resort

farm, Trequanda
Borgo Sant'Ambrogio - Resort is located in the Tuscan countryside near Pienza, a short drive from Siena and Arezzo, offering stunning views of the Val d'Orcia. The resort has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The resort features a traditional Tuscan design with a garden and barbecue facilities. Guests can enjoy a seasonal outdoor pool, a restaurant, a bar, a fitness centre and free Wi-Fi, as well as bike and car hire for exploring the surrounding countryside.
Suite Gioconda - Podere Casa Rossa In Pienza - Pienza
10 5 reviews

Suite Gioconda - Podere Casa Rossa In Pienza

apartment, Pienza
This family-friendly farmhouse, near Pienza's historic centre, offers a peaceful rural setting a short 0.6km walk from the Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile.
Sleeping four guests in two bedrooms and one bathroom, this self-catering property boasts a garden, air conditioning, Wi-Fi, a dishwasher, and parking, plus housekeeping is available on request.
Dimora Del Corso Di Montepulciano - Pienza
9.1 530 reviews

Dimora Del Corso Di Montepulciano

apartment, Montepulciano
Dimora Del Corso Di Montepulciano is situated in the historic centre of Montepulciano, just 9.3 miles from the UNESCO-protected town of Pienza. The apartment is highly rated for location, cleanliness, and overall experience.
This one-bedroom apartment offers a comfortable and stylish space for a relaxing stay. Guests can enjoy modern amenities like air conditioning, free Wi-Fi, and a dishwasher, alongside a terrace, a garden, and a swimming pool.

Best Pienza holiday rentals with parking

Agriturismo San Marcello - Pienza
9.3 360 reviews

Agriturismo San Marcello

farm, Castiglione d'Orcia
Agriturismo San Marcello is located in Castiglione d'Orcia, a short drive from the thermal baths of Bagno Vignoni and Bagni San Filippo, offering a peaceful escape in the Tuscan countryside. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The farm offers spacious accommodation units, some with fully equipped kitchens and private bathrooms. Guests can enjoy a continental breakfast, relax on the sun terrace, or explore the surrounding area with skiing and cycling opportunities.
Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza
Farm for 3 guests. Your accommodation will be based in Pienza.
Facilities and services include a washing machine, air conditioning and free parking. This accommodation also has a garden!
Agriturismo Il Noce - Pienza
8.0 2 reviews

Agriturismo Il Noce

apartment, Castiglione d'Orcia
Agriturismo Il Noce offers a tranquil apartment stay in Castiglione d'Orcia, featuring garden views and a private entrance, with free high-speed Wi-Fi and parking.
This pet-friendly dwelling includes a fully equipped kitchen, air conditioning, a modern bathroom, and provides bed linen and towels, with proximity to cycling routes and a sauna for guest enjoyment.
House Dreams Toscany - Pienza
8.2 27 reviews

House Dreams Toscany

apartment, Chianciano Terme
This apartment is situated in Chianciano Terme, just 5.2 km from the Terme di Montepulciano spa complex and 23 km from the charming medieval village of Bagno Vignoni, known for its natural hot springs. The surrounding area offers a peaceful and quiet setting, perfect for a relaxing getaway.
This two-bedroom, two-bathroom property spans 130 square metres and comfortably accommodates up to 11 guests. The apartment features a well-equipped kitchen, air conditioning, a private terrace and balcony, a garden, free Wi-Fi, and private parking, ensuring a comfortable and enjoyable stay.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town to explore, with its charming cobbled streets and stunning views. You can visit the Duomo, a magnificent cathedral built in the 15th century, or the Palazzo Piccolomini, a grand Renaissance palace. For a scenic drive, head to the nearby Val d'Orcia, a stunning landscape dotted with rolling hills, vineyards, and cypress trees.
  • 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?

    The best walking route is the 'Sentiero della Bonifica', a scenic trail that follows the old irrigation canals and offers stunning views of the Val d'Orcia. For cycling, the 'Strada del Vino Nobile di Montepulciano' is a popular route that winds through vineyards and offers picturesque views of the surrounding countryside.
  • 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 other towns or cities can be easily accessed from Pienza?

    You can easily visit nearby towns like Montepulciano, a charming town known for its wine production, and Montalcino, another beautiful hilltop town famous for its Brunello di Montalcino wine. Siena, a larger city with a historic centre, is also within easy reach.
  • 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 amenities are commonly available in vacation rentals in Pienza?

    Vacation rentals in Pienza typically offer basic amenities like a kitchen, bathroom, and bedrooms. Many also have a private garden or terrace, and some even have a swimming pool. You can find rentals with a range of amenities to suit your needs and budget.
  • 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 time of year is best to rent a vacation rental Pienza?

    Pienza is beautiful year-round, but the best time to visit is during 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.
  • 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 are the local dishes in Pienza region?

    The region is famous for its pecorino cheese, made from sheep's milk. Be sure to try the 'Pecorino di Pienza', a local variety of pecorino cheese that is particularly creamy and delicious. Other local specialities include 'Pici cacio e pepe', a pasta dish made with pecorino cheese and black pepper, and 'Ribollita', a hearty Tuscan bread soup.

Popular destinations

Best Pienza holiday rentals with a balcony

Agriturismo Il Gonzeto, Montepulciano - Pienza
9.0 345 reviews

Agriturismo Il Gonzeto, Montepulciano

farm, Montepulciano
Agriturismo Il Gonzeto is a farm stay located in the countryside near Montepulciano, just 1.3 miles from the thermal baths of Montepulciano Terme and a short drive from the medieval town of Montepulciano. This property has received very good user ratings, with excellent ratings for location and cleanliness.
The farm offers a variety of rooms and apartments, each with modern amenities such as air conditioning, free Wi-Fi, and flat-screen TVs. Guests can enjoy a delicious breakfast, relax by the infinity pool, or explore the surrounding countryside.
Agriturismo Podere San Pietro - Pienza
9.9 139 reviews

Agriturismo Podere San Pietro

farm, Montepulciano
Agriturismo Podere San Pietro is located in the Tuscan countryside, just 2 kilometres from the historic centre of Montepulciano and 10 kilometres from Chianciano Terme. The property has received excellent ratings for location, cleanliness and overall experience.
The self-catering apartment has three bedrooms, one bathroom and a furnished patio. Amenities include a kitchen with a fridge, a washing machine, free toiletries and a hairdryer, as well as a fitness centre, a garden, a terrace and free private parking.
Agriturismo Ardene - Pienza
9.2 61 reviews

Agriturismo Ardene

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.
Casa In Chiana - Pienza
10 67 reviews

Casa In Chiana

apartment, Torrita di Siena
Casa in Chiana, a recently renovated apartment in Torrita di Siena, is situated 16km from Montepulciano Terme and 45km from Piazza Grande in Arezzo.
This 50-square-metre self-catering flat offers one bedroom, one bathroom, a private garden, swimming pool, tennis court, free Wi-Fi, and free bikes for exploring the Tuscan countryside, sleeping up to two guests.

Best pet friendly Pienza holiday rentals

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

La Terrazza Del Papa - Pienza
9.8 14 reviews

La Terrazza Del Papa

apartment, Pienza
La Terrazza del Papa is a tranquil apartment situated in Pienza, located 14 kilometres from Bagno Vignoni and 26 kilometres from Bagni San Filippo, with Mount Amiata 45 kilometres away.
This 64 square metre apartment offers air conditioning, complimentary WiFi, a fully equipped kitchen, and accommodation for up to seven guests across two bedrooms and one bathroom, with check-out between 8am and 11am.
Frattina1860
Romantic Apartment
Free Parking - Pienza
9.8 25 reviews

Frattina1860 Romantic Apartment Free Parking

apartment, Montalcino
This self-catering apartment is situated in the Crete Senesi, 12km from Pienza, 30 minutes’ drive from Montalcino and Montepulciano, offering easy access to the A1 motorway (20 minutes from the exit).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen (microwave, coffee machine, kettle), air conditioning, parking, internet access, complimentary breakfast, and welcome bathroom amenities.
Locanda Di Montisi Contrada Room Among The Hills Of Montalcino - Pienza
No reviews

Locanda Di Montisi Contrada Room Among The Hills Of Montalcino

apartment, Montalcino
This one-bedroom flat is located in the medieval village of Montisi, within the Crete Senesi region, offering a convenient base for exploring notable Tuscan towns such as Siena (approximately 50 kilometers away), Pienza (approximately 30 kilometers away), Montalcino (approximately 20 kilometers away), and Montepulciano (approximately 35 kilometers away).
This property accommodates two guests and features a traditional Tuscan style with exposed beams and terracotta floors, providing air conditioning, Wi-Fi, a TV, and self check-in, with nearby opportunities for spa visits, food and wine tours, and cycling.
Red Heart - Relax With Those You Love In Tuscany. - Pienza
No reviews

Red Heart - Relax With Those You Love In Tuscany.

house, Trequanda
This six-bedroom villa in Trequanda is a five-minute walk from the Val di Chiana, 16 minutes (approx. 26km) from Crete Senesi, and 20 minutes (approx. 32km) from Valdichiana Outlet Village.
The property offers ample space for 14 guests, boasting four bathrooms, WiFi, air conditioning, a jetted bathtub, and proximity to the Terme di Montepulciano Spa.
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