Holiday Rentals in Pienza

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

156 M² Villa ∙ 3 Makuuhuonetta ∙ 6 Vierasta - Pienza
No reviews

156 M² Villa ∙ 3 Makuuhuonetta ∙ 6 Vierasta

house, Trequanda
Accommodation for up to 6 people. This accommodation is located in Trequanda.
Facilities and services: a kitchen, a terrace and free parking. Take advantage of the garden in this house!
Villa Mulinello, Secluded, Panoramic Views Over Montepulciano Valley - Pienza
No reviews

Villa Mulinello, Secluded, Panoramic Views Over Montepulciano Valley

apartment, Torrita di Siena
This restored 17th-century tower villa, offering panoramic views of Montepulciano, the valley, Monte Amiata, and the Val d'Orcia hills, is situated within the Capanne di Sopra estate, 1.3 kilometres from Montefollonico and 7 kilometres from Montepulciano.
This family-friendly apartment, accommodating up to six guests, features three bedrooms, two bathrooms, Wi-Fi, a kitchen with a fridge and dishwasher, a garden, and private parking, with two fireplaces and a barbecue adding to its appeal.
Lovely Home In San Quirico D'orcia - Pienza
9.1 32 reviews

Lovely Home In San Quirico D'orcia

apartment, San Quirico d'Orcia
This four-bedroom, two-bathroom holiday home in San Quirico d'Orcia sits amidst vineyards, offering stunning views and proximity to the historic centre and the Renaissance garden of the Santa Maria Assunta church.
Sleeping eight guests, the property features a fully equipped kitchen with fridge and dishwasher, Wi-Fi, and outdoor space; nearby wine and olive oil tasting experiences enhance the Tuscan countryside stay.
Villa Limone - 3 Bedroom Villa In Tuscany - Pienza
9.5 36 reviews

Villa Limone - 3 Bedroom Villa In Tuscany

house, Torrita di Siena
Villa Limone is a 3-bedroom, 3-bathroom property located in Cignella, a village just 2 kilometres from the historic town of Torrita di Siena.
The villa boasts a spacious and open-plan layout perfect for families or groups, with a fully equipped kitchen, a private garden, a swimming pool, and a jacuzzi.

Best Pienza holiday rentals with parking

Masseria Del Bosco Poderuccio - Pienza
8.5 56 reviews

Masseria Del Bosco Poderuccio

farm, Chianciano Terme
Masseria del Bosco Poderuccio, a self-catering property in Chianciano Terme, is conveniently located near Montepulciano Terme (14km), Bagno Vignoni (21km), and Bagni San Filippo (21km), offering easy access to renowned thermal baths.
This one-bedroom cottage boasts 16 square metres of space, a private garden, swimming pool, free Wi-Fi, and parking, perfect for a couple seeking a relaxing Tuscan getaway with stunning mountain views.
Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Master Double Bedroom Wit - Pienza
No reviews

Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Master Double Bedroom Wit

house, Trequanda
Cignella Villa Peach, a three-bedroom holiday home in Trequanda, Tuscany, is situated near the Val di Chiana valley and within 15km of the Saints Peter and Andrew Church and the Sant'Anna in Camprena Monastery.
This 156-square-metre property offers three bathrooms, a private garden, swimming pool, and sleeps up to six guests, boasting a fully equipped kitchen, fireplace, and TV with DVD player.
Dimora Del Poggio Deluxe Apartment, Cozy & Elegant - Pienza
10 33 reviews

Dimora Del Poggio Deluxe Apartment, Cozy & Elegant

apartment, San Quirico d'Orcia
This San Quirico d'Orcia apartment, ideally located near the Horti Leonini and Collegiate Church, offers easy walking access to the town's key attractions.
The self-catering flat comprises one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher; air conditioning and parking are also provided.
60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Pienza
No reviews

60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

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.

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.

Popular destinations

Best Pienza holiday rentals with a balcony

Agriturismo Palazzo Conti A - Pienza
9.3 146 reviews

Agriturismo Palazzo Conti A

house, San Quirico d'Orcia
Agriturismo Palazzo Conti A is located just outside Pienza, a short drive from Montalcino, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartments are classically decorated and feature flat-screen TVs, seating areas, and fully equipped kitchenettes. Guests can enjoy a range of amenities including a swimming pool, a natural pool, a garden with BBQ facilities, a spa, a restaurant, a bar, and room service.
Casa Di Isma - Pienza
No reviews

Casa Di Isma

apartment, San Quirico d'Orcia
This two-bedroom flat in San Quirico d'Orcia offers a prime location, situated a mere 4-minute walk from the Jardins Leonini and 6 minutes from Palazzo Chigi, with Pienza's historic centre just a 12-minute drive away.
This San Quirico d'Orcia apartment accommodates up to six guests and includes essential amenities such as internet and air conditioning, providing a convenient base for exploring the surrounding Tuscan landscape and nearby cultural sites like Artemisia gallery.
Hotel Apartment "Villa Limone" With Shared Pool & Wi-fi - Pienza
No reviews

Hotel Apartment "Villa Limone" With Shared Pool & Wi-fi

house, Trequanda
This villa apartment is located in Trequanda, a short drive from the Val di Chiana and the historic centre of Pienza, with Artemisia Gallery and Palazzo Borgia nearby.
This property offers 156 square meters of living space for up to 6 guests, featuring 3 bedrooms, 3 bathrooms, air conditioning, Wi-Fi, a shared swimming pool, and on-site parking.
Apartment Rosmarino- Cignella Resort Tuscany - Pienza
No reviews

Apartment Rosmarino- Cignella Resort Tuscany

chalet, Trequanda
Apartment Rosmarino, a chalet in Osteria Delle Noci, is located 47 kilometres from Piazza Grande and 17 kilometres from Montepulciano Terme, offering a convenient base for exploring Trequanda and its surroundings.
This air-conditioned chalet spans 93 square metres, accommodating up to seven guests across two bedrooms and two bathrooms, and features a fully equipped kitchen, WiFi, a private entrance, and access to a shared swimming pool, with Bagno Vignoni 24 kilometres and Bagni San Filippo 39 kilometres away.

Best pet friendly Pienza holiday rentals

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

La Casa Di Vignoni Alto - Pienza
8.6 65 reviews

La Casa Di Vignoni Alto

house, San Quirico d'Orcia
La Casa di Vignoni Alto is a holiday home located in the village of Bagno Vignoni, 1.9 kilometres from the famous thermal baths and a short drive from other attractions such as Bagni San Filippo (19 kilometres) and Montepulciano Terme (29 kilometres).
The 250 square metre property features two bedrooms, two bathrooms, and can accommodate up to nine guests, and offers amenities such as a fully equipped kitchen, a garden, a tennis court, and free Wi-Fi.
La Cantina Apartment - Agriturismo Il Noce In Val D'orcia - Pienza
No reviews

La Cantina Apartment - Agriturismo Il Noce In Val D'orcia

apartment, Castiglione d'Orcia
La Cantina Apartment, a one-bedroom flat in Castiglione d'Orcia, Tuscany, is located 33 kilometres from Mount Amiata and 4 kilometres from Bagno Vignoni, offering a rural Tuscan experience within Agriturismo Il Noce, close to Fortress of Tentennano and Piazza delle Sorgenti. This pet-friendly accommodation for three guests provides a private kitchen, air conditioning, Wi-Fi, and access to on-site spa facilities for an additional fee, with bike rental available for exploring the surrounding cycling routes.
Agriturismo Lunadoro - Pienza
9.2 100 reviews

Agriturismo Lunadoro

farm, Pienza
Agriturismo Lunadoro is located in the Tuscan countryside, 9 kilometres from the historic town of Pienza, and within a one-hour drive of Siena and Arezzo. The farm has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
This rural retreat offers a range of rooms and apartments, all featuring rustic charm and modern comforts. Guests can enjoy a refreshing swim in the outdoor pool, relax in the furnished garden, and prepare meals in the kitchenette.
Artistica Pienza | Breathtaking Val D'orcia View - Pienza
9.3 231 reviews

Artistica Pienza | Breathtaking Val D'orcia View

apartment, Pienza
Artistica apartment, a two-bedroom flat in Pienza's historic centre, is situated directly on the ancient walls walkway, offering unparalleled views of the Orcia Valley.
This self-catering property sleeps five, features a fireplace, a fully equipped kitchen including a fridge and microwave, air conditioning, parking, and internet access; nearby attractions include Pienza's main piazza and other historical sites (distances unspecified).
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