Holiday Rentals in Pienza

69 available vacation rental offers

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Pienza holiday rentals
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Pienza holiday rentals: compare the best deals

Best family friendly Pienza holiday rentals

Among the 69 accommodations in Pienza, here are the 4 best family friendly rentals

Comodo Appartamento Centrale Dimora Delle Mura - Pienza
9.9 113 reviews
Pienza
06/27 – 06/29
HK$1214/nighttotal: HK$2428 (2 )

Comodo Appartamento Centrale Dimora Delle Mura

1 2
apartment , San Quirico d'Orcia
This apartment is ideally located on the street running alongside the ancient walls of San Quirico d'Orcia's historic centre, putting you within walking distance of the town's main attractions, including the Horti Leonini gardens and the Collegiate Church. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom apartment comfortably accommodates four guests and offers a fully equipped kitchen with all the amenities you need to prepare meals at home. You can enjoy the peace and quiet of the historic centre while still being close to the charming Tuscan countryside and the town's attractions.
150 M² House ∙ 4 Bedrooms ∙ 8 Guests - Pienza
8.1 10 reviews
Pienza
06/27 – 06/29
HK$3275/nighttotal: HK$6550 (2 )

150 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , San Quirico d'Orcia
This Tuscan villa is situated near San Quirico d'Orcia, offering easy access to the town's attractions and the Church of Santa Maria Assunta's Renaissance garden.
The 150 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a kitchen with a fridge and dishwasher, plus a terrace, garden, parking, and internet access.
La Mandola - Pienza
9.2 56 reviews
Pienza
09/07 – 09/18
HK$879/nighttotal: HK$9669 (11 )

La Mandola

2 2
apartment , Castiglione d'Orcia
La Mandola is a pet-friendly apartment situated in Rocca d'Orcia, just 3.3 miles from the thermal baths of Bagno Vignoni and within easy reach of Siena and Saturnia. This apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers two bedrooms and a bathroom, spanning 80 square metres. Guests can enjoy a fully equipped kitchen, a comfortable living space, a flat-screen TV, and private parking.
Agriturismo Palazzo Conti - B - Pienza
8.1 92 reviews
Pienza
07/04 – 07/12
HK$1666/nighttotal: HK$13328 (8 )

Agriturismo Palazzo Conti - B

1 2
farm , San Quirico d'Orcia
Agriturismo Palazzo Conti - B is situated in Pienza, a charming town in the Val d'Orcia, just 22 miles from Siena and 29 miles from Arezzo, making it an ideal base for exploring the Tuscan countryside. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The farm offers comfortable accommodation for up to four guests, with a fully equipped kitchen and a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace or in the garden, and benefit from free Wi-Fi and parking.

Best Pienza holiday rentals with parking

Le Checche - Pienza
9.6 217 reviews
Pienza
07/28 – 07/31
HK$5001/nighttotal: HK$15003 (3 )

Le Checche

2 5
farm , Pienza
Le Checche is a farm stay situated 35 kilometres from Mount Amiata, near Pienza, with Bagno Vignoni 8.7 kilometres away and Bagno San Filippo 16 kilometres distant.
This family-friendly property offers a range of amenities including a swimming pool, hot tub, restaurant, and outdoor play equipment, making it a perfect choice for families seeking a relaxing rural retreat.
60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Pienza
Pienza
09/07 – 09/18
HK$1249/nighttotal: HK$13739 (11 )

60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

1 2
apartment , Pienza
This Pienza flat, situated in the Val d'Orcia, offers direct views of the UNESCO-listed medieval village and is 17 kilometres from Montepulciano's thermal baths.
This 45 square metre flat accommodates up to four guests, featuring one bedroom, one bathroom, free Wi-Fi, and a fully equipped kitchen, providing an authentic Tuscan experience with easy access to nearby attractions.
80 M² House ∙ 2 Bedrooms ∙ 4 Guests - Pienza
Pienza
06/27 – 06/29
HK$1232/nighttotal: HK$2464 (2 )

80 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Trequanda
This recently renovated two-bedroom apartment, offering countryside views from its windows, is located in a quiet spot within a small village in Trequanda, providing convenient walking access to local amenities and public transport.
This 80 square meter dwelling accommodates up to four guests and features a fully equipped modern kitchen, a cozy lounge, a ground floor bedroom with a queen-size bed, a modern bathroom, and a second bedroom with two single beds and an en-suite bathroom, with self check-in available.
120 M² House ∙ 2 Bedrooms ∙ 8 Guests - Pienza
10 1 review
Pienza
06/27 – 06/29
HK$1092/nighttotal: HK$2184 (2 )

120 M² House ∙ 2 Bedrooms ∙ 8 Guests

2 2
house , Trequanda
Vacation house to rent for 8 guests with an excellent rating of 100% based on 1 reviews. This accommodation is located in Trequanda.
Facilities and services include a washing machine, free parking and a kitchen.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza itself is a must-see, with its stunning Renaissance architecture and the iconic Piazza Pio II. Just outside of town, you can visit the Corsignano Castle, a 14th-century fortress, or the charming village of Monticchiello, known for its annual theatrical performances.
  • 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 Val d'Orcia, a UNESCO World Heritage Site, offers some beautiful walks and bike rides. You can follow the Via Francigena, an ancient pilgrimage route, or explore the rolling hills and vineyards on a more leisurely cycle. The panoramic views from the top of Monte Amiata are also worth the climb.
  • 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?

    Hiking, cycling, and horseback riding are popular activities in the area. If you are looking for something more adventurous, you can try paragliding from the top of Monte Amiata or go rock climbing in the nearby Val d'Orcia.
  • 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?

    Pienza is well-connected to other Tuscan towns. You can easily visit Siena, Montepulciano, and San Quirico d'Orcia by car or bus. For a day trip, consider visiting the charming medieval town of Montalcino, known for its Brunello di Montalcino wine.
  • 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?

    Many vacation rentals in Pienza offer amenities like Wi-Fi, air conditioning, and private parking. Some rentals also have kitchens, laundry facilities, and outdoor spaces like patios or gardens.
  • 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 generally the best times to visit Pienza, as the weather is mild and the crowds are smaller. Summer can be hot and crowded, while winter can be chilly and rainy.
  • What are the local dishes in Pienza region?

    Pienza is famous for its Pecorino cheese, made from sheep's milk. Try the Pecorino di Pienza DOP, a protected designation of origin cheese. Other local specialties include the ribollita, a hearty bread soup, and the pici, a thick hand-rolled pasta.

Destinations nearby

Best Pienza holiday rentals with a balcony

La Casa Nel Borgo - Pienza
9.8 952 reviews
Pienza
08/09 – 08/10
HK$1821/nightfor 1 night

La Casa Nel Borgo

2 4
house , Pienza
La Casa nel Borgo is situated in Monticchiello, a charming village just 10.5 kilometres from Pienza and 43 kilometres from Mount Amiata, offering a peaceful escape while being within easy reach of popular destinations. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house provides a comfortable and well-equipped space for your stay, featuring a private garden and a terrace. It includes modern amenities such as air conditioning, free Wi-Fi, a washing machine, and a fully equipped kitchen with a dishwasher.
Agriturismo Cavalierino - Pienza
9.2 613 reviews
Pienza
07/21 – 07/23
HK$2736/nighttotal: HK$5472 (2 )

Agriturismo Cavalierino

2 2
farm , Montepulciano
Agriturismo Cavalierino is located in the countryside outside Montepulciano, about 4.6 miles from the town's thermal baths and 31 miles from Mount Amiata, offering a peaceful escape from the bustling town centre. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property features a swimming pool, jacuzzi, terrace, garden, and fitness centre, providing ample opportunities for relaxation and recreation. Guests can enjoy a daily Italian breakfast and select rooms offer kitchenettes, allowing for self-catering options.
Borgo La Grancia - Pienza
9.7 48 reviews
Pienza
09/07 – 09/18
HK$1665/nighttotal: HK$18315 (11 )

Borgo La Grancia

1 2
resort , Montalcino
Borgo La Grancia is located in Montisi, a charming village just 10 kilometres from the historic town of Montalcino, famous for its Brunello wine, and offers a peaceful escape from the hustle and bustle. The resort has excellent user, location and cleanliness ratings.
The resort offers comfortable rooms with private bathrooms and some even have kitchens. Guests can enjoy a range of amenities including a swimming pool, garden, terrace, table tennis, free bikes and free Wi-Fi.
La Chiusa Dei Monaci - Pienza
9.1 180 reviews
Pienza
09/07 – 09/18
HK$1086/nighttotal: HK$11946 (11 )

La Chiusa Dei Monaci

1 2
farm , Trequanda
La Chiusa dei Monaci is a farm stay located in Castelmuzio, a small village near Trequanda, just 50 km from both Siena and Arezzo, offering a peaceful escape from the hustle and bustle. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The farm stay offers a 40 square metre, one-bedroom apartment with a fully equipped kitchen, perfect for a family of four. Guests can enjoy the private terrace with stunning views, the garden, and barbecue facilities for al fresco dining.

Best pet friendly Pienza holiday rentals

Among the 69 accommodations in Pienza, here are the 4 best pet friendly rentals

La Falegnameria - Pienza
9.6 19 reviews
Pienza
07/13 – 07/15
HK$1028/nighttotal: HK$2056 (2 )

La Falegnameria

1 2
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.
Podere Villa Rosa  Torrita Di Siena - Pienza
9.5 4 reviews
Pienza
06/27 – 06/28
HK$3760/nightfor 1 night

Podere Villa Rosa Torrita Di Siena

2 4
apartment , Torrita di Siena
This Torrita di Siena apartment, a short drive from Siena (approx. 30km) and other Tuscan towns like Montepulciano and Pienza, offers stunning mountain views.
The 90m² self-catering flat sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, a private balcony with barbecue, on-site parking, and a washing machine.
Luxury 6br Val D'orcia Villa With Pool & Views - Pienza
10 1 review
Pienza
08/16 – 08/19
HK$13772/nighttotal: HK$41316 (3 )

Luxury 6br Val D'orcia Villa With Pool & Views

6 13
house , Sarteano
Villa Sambuco, a luxury Tuscan property near Sarteano, enjoys stunning 360° views of the Val d'Orcia, a UNESCO World Heritage site, and is situated between Sarteano and Radicofani in the Valdichiana and Val d'Orcia regions.
This six-bedroom, seven-bathroom villa sleeps 13, boasts a heated infinity pool, private gym, extensive gardens, and features a fully equipped kitchen, including a dishwasher; guests can also enjoy fresh produce from the on-site vegetable garden, henhouse, and orchard.
Stunning Apartment In Monticchiello - Pienza
9.2 22 reviews
Pienza
06/29 – 07/02
HK$2062/nighttotal: HK$6186 (3 )

Stunning Apartment In Monticchiello

1 3
apartment , Pienza
This spacious three-bedroom apartment, sleeping up to 15 guests, is located in Monticchiello, a peaceful village 10.5km from Montepulciano and within easy reach of Bagno Vignoni and Bagni San Filippo thermal baths.
The 195 square metre property boasts a fully equipped kitchen with dishwasher, air conditioning, private parking, Wi-Fi, a terrace, and two bathrooms, perfect for families or large groups visiting Pienza.
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