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Holiday Rentals in Pienza

114 available vacation rental offers

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114 Holiday Rentals and Airbnb in Pienza

Agriturismo I Capraccioni Monticchiello - Pienza - Pienza
9.3 184 reviews
Pienza
2 1
NZ$166/nighttotal: NZ$332 (2 )

Agriturismo I Capraccioni Monticchiello - Pienza

gîte - Pienza
This self-catering apartment, situated in the Val d'Orcia countryside, is 4km from Montepulciano and 2.5km from Monticchiello, offering easy access to these historic Tuscan towns.
The 80 sq m ground-floor property sleeps two, features a private garden with children's play area and barbecue, and includes a kitchen, bathroom, and on-site parking.
70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Pienza
Pienza
3 2
NZ$550/nightfor 1 night

70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment - Trequanda
This 70 square meter flat is located in the historic centre of Petroio, a village celebrated for its terracotta production, offering panoramic views of the Val d'Orcia and immediate access to the main square, just 100 meters away.
This pet-friendly apartment accommodates up to four guests, featuring two bedrooms, one bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, and is situated close to the Terracotta Museum.
Agriturismo Il Noce - Pienza
8.8 4 reviews
Pienza
2 2
NZ$280/nighttotal: NZ$560 (2 )

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.
Soleluna - Pienza
9.8 64 reviews
Pienza
2 1
NZ$250/nighttotal: NZ$500 (2 )

Soleluna

apartment - San Quirico d'Orcia
The SoleLuna apartment is located in San Quirico d'Orcia, Tuscany, 5.8km from Bagno Vignoni and 26km from Montepulciano Terme, offering easy access to these thermal spa towns and other Tuscan attractions.
This 45 square metre flat features one bedroom, a living room, and one bathroom, sleeping up to three guests and including a fully equipped kitchen with a dishwasher, microwave, fridge, air conditioning, and free Wi-Fi.
Finestra Dell'angelo Centro Storico - Pienza
10 5 reviews
Pienza
2 1
NZ$223/nighttotal: NZ$669 (3 )

Finestra Dell'angelo Centro Storico

apartment - Pienza
This Pienza flat, located in a Renaissance palazzo with dual street access to Corso Rossellino and Via Della Rosa, offers direct immersion in the historic centre, placing you within 100 metres of Pienza Cathedral and the Palazzo Piccolomini.
This spacious flat accommodates four guests with one bathroom, featuring high-speed Wi-Fi and a kitchen, providing an ideal base for exploring Pienza's Renaissance architecture and local attractions.
Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.5 64 reviews
Pienza
2 2
NZ$390/nighttotal: NZ$2340 (6 )

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm - Pienza
Farm for 5 people with an excellent rating of 95% based on 64 reviews. You will be in Pienza.
Facilities and services include a barbecue, free parking and a swimming pool. This accommodation also has a garden!
Appartamento Con Vista - Montepulciano - Pienza
10 15 reviews
Pienza
2 1
NZ$251/nightfor 1 night

Appartamento Con Vista - Montepulciano

apartment - Montepulciano
This Montepulciano apartment, situated just outside the historic centre walls, offers a peaceful countryside setting a short distance from the town's attractions.
The self-catering property features one bedroom, one bathroom, and sleeps three guests; amenities include a fully equipped kitchen, air conditioning, Wi-Fi, private parking, and a panoramic balcony with stunning Val d'Orcia views.
70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
10 6 reviews
Pienza
2 1
NZ$971/nightfor 1 night

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.
Agriturismo Riposati - Pienza
9.6 255 reviews
Pienza
2 2
NZ$288/nighttotal: NZ$864 (3 )

Agriturismo Riposati

house - Pienza
This house is located near Monticchiello, a charming village just 2 kilometres away, and a short 20-minute drive from the famous town of Montepulciano. It has received excellent ratings for location, cleanliness and user experience.
The house has one bathroom and features a fully equipped kitchen, a garden and free Wi-Fi. Guests can enjoy stunning views of the Val d'Orcia hills and relax in the tranquil garden setting.
La Casa Di Nonna Milia - Pienza
9.3 45 reviews
Pienza
2 2
NZ$188/nighttotal: NZ$752 (4 )

La Casa Di Nonna Milia

apartment - Castiglione d'Orcia
This two-bedroom house is located in the historic centre of Castiglione d'Orcia, within easy walking distance of local shops, restaurants and a pizzeria.
The property features a fully equipped kitchen, including a microwave oven, and can accommodate up to four guests, making it ideal for families or groups of friends exploring the beautiful Val d'Orcia region.
Vacanze A Piandimaggio In Val D'orcia. - Pienza
9.6 201 reviews
Pienza
2 2
NZ$200/nighttotal: NZ$800 (4 )

Vacanze A Piandimaggio In Val D'orcia.

gîte - Pienza
This charming farmhouse is situated in the Val d'Orcia natural park, just a short distance from the picturesque town of Pienza and the unique thermal baths of Bagno Vignoni, offering stunning views of Mount Amiata. The property has received excellent ratings for location, cleanliness, and overall user experience.
The gîte offers multiple apartments, suitable for families or groups of friends, with a capacity of up to four guests. Guests can enjoy a shared swimming pool, a solarium, and a peaceful countryside setting, perfect for relaxing and exploring the surrounding area.
La Casina Di Sangallo, Tower Around - Pienza
9.4 459 reviews
Pienza
2 2
NZ$350/nightfor 1 night

La Casina Di Sangallo, Tower Around

apartment - Montepulciano
La casina di Pulcinella is a charming apartment situated just outside the historic centre of Montepulciano, offering a peaceful retreat within easy reach of the town's attractions and the thermal baths of Montepulciano Terme. It boasts excellent ratings for location, cleanliness, and user experience.
The apartment features one bedroom and one bathroom, as well as a fully equipped kitchen for preparing meals. Guests can enjoy a range of amenities including a flat-screen TV, parquet floors, and comfortable bathrobes, and can take advantage of the bicycle rental service to explore the picturesque Tuscan countryside.

Best family friendly Pienza holiday rentals

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

200 M² Farmhouse ∙ 4 Bedrooms ∙ 8 Guests - Pienza
Pienza
2 4
NZ$2467/nighttotal: NZ$4934 (2 )

200 M² Farmhouse ∙ 4 Bedrooms ∙ 8 Guests

farm - Torrita di Siena
Farm listing for 8 people. Your accommodation will be located in Torrita di Siena.
Services and facilities: event friendly rooms, a freeze and a garden. Enjoy a swimming pool in this accommodation in Torrita di Siena!
Casa Vacanze Oliviera Pienza - Pienza
9.6 22 reviews
Pienza
2 1
NZ$287/nighttotal: NZ$1148 (4 )

Casa Vacanze Oliviera Pienza

apartment - Pienza
This one-bedroom apartment is conveniently located near Pienza, just a short drive from popular destinations like Bagno Vignoni, Montepulciano Terme, and Bagni San Filippo, allowing you to easily explore the Tuscan countryside. The apartment has received very good ratings for cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The flat is 35 square metres in size and features a fully equipped kitchenette, free Wi-Fi, and comfortable amenities like towels, bed linen, and a hairdryer. You can enjoy activities like fishing and hiking in the surrounding area, and pets are welcome.
Chez Anna - Pienza
8.6 10 reviews
Pienza
2 2
NZ$385/nighttotal: NZ$770 (2 )

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.
La Casina Room - Pienza
9.5 2 reviews
Pienza
2 1
NZ$170/nighttotal: NZ$4760 (28 )

La Casina Room

apartment - Trequanda
This recently renovated one-bedroom flat in Castelmuzio is located 48 kilometres from Piazza Grande and Piazza del Campo, with Parco dei Mulini 19 kilometres away and Bagni San Filippo 35 kilometres distant.
This 25 square metre apartment accommodates two guests and features air conditioning, complimentary WiFi, a kitchenette with a fridge and microwave, and a private balcony, with an on-site minimarket and bicycle parking available.

Best Pienza holiday rentals with parking

Agriturismo Sant'ansano - Pienza
9.6 139 reviews
Pienza
2 1
NZ$256/nighttotal: NZ$7168 (28 )

Agriturismo Sant'ansano

farm - Castiglione d'Orcia
Agriturismo Sant'Ansano is a farmhouse stay in Castiglione d’Orcia, Tuscany, located 9.2km from Bagno Vignoni and 30.6km from Mount Amiata.
This air-conditioned property offers a swimming pool, garden, free Wi-Fi, and barbecue facilities, along with a kitchen equipped with a fridge, microwave, and dishwasher; pets are welcome.
Casa In Campagna Casagori - Pienza
9.4 85 reviews
Pienza
2 1
NZ$418/nighttotal: NZ$836 (2 )

Casa In Campagna Casagori

farm - Pienza
Casa in Campagna Casagori is a farm stay in Pienza, located 45 kilometres from Mount Amiata and 14 kilometres from Bagno Vignoni.
This 16-square-metre farm offers one bedroom, one bathroom, and accommodation for up to three guests, with amenities including air conditioning, Wi-Fi, a garden, terrace, bar, and on-site parking, plus daily Italian breakfast.
Agriturismo Marinello - Pienza
9.4 612 reviews
Pienza
2 1
NZ$333/nighttotal: NZ$2331 (7 )

Agriturismo Marinello

farm - Pienza
Agriturismo Marinello is located in the Val d’Orcia, a UNESCO World Heritage Site, just 4km from the centre of Pienza and a 32km drive from Montalcino. The farm has received excellent ratings for location, cleanliness and overall experience.
The farm offers both rooms and apartments, all with traditional Tuscan features, like wood-beamed ceilings and wrought-iron beds. Guests can enjoy a private garden, a swimming pool open from May to September, and a fully equipped kitchen.
Podere Le Querci A Charming Cottage In Val D'orcia - Pienza
9.9 69 reviews
Pienza
2 1
NZ$294/nighttotal: NZ$1176 (4 )

Podere Le Querci A Charming Cottage In Val D'orcia

chalet - Trequanda
Podere le Querci, a self-catering apartment near Castelmuzio in the Val d'Orcia, is situated approximately 6km from Trequanda and offers stunning views, close proximity to Montalcino, Montepulciano, and Pienza, and is within easy reach of the A1 motorway.
This one-bathroom property sleeps up to four guests, featuring a king-size bed, sofa bed, and optional children's bed, a functional fireplace, a fully equipped kitchen with fridge and microwave, private parking, a garden within a 6-hectare olive grove, and allows pets; guests can explore the olive grove and sample the organic olive oil produced on-site, and visit the Convent of Saint Anna in Camprena, a filming location for 'The English Patient'.

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 Sant'agostino - Pienza
8.8 72 reviews
Pienza
2 1
NZ$258/nightfor 1 night

Agriturismo Sant'agostino

farm - Montalcino
Agriturismo Sant'Agostino, a renovated farmhouse near San Giovanni d'Asso, is situated approximately 42km from Siena's Piazza del Campo and 22km from Bagno Vignoni, offering easy access to the Val d'Orcia and its renowned wineries.
This self-catering property features a swimming pool, a terrace, a garden, free Wi-Fi, and private parking; selected rooms include kitchens with dishwashers, and all rooms are air-conditioned.
Brunhouse - Pienza
9.1 33 reviews
Pienza
2 2
NZ$349/nighttotal: NZ$1047 (3 )

Brunhouse

house - San Quirico d'Orcia
Brunhouse is located in a peaceful setting just 5km from the charming spa town of Bagno Vignoni, 40km from Mount Amiata and 45km from Piazza del Campo in Siena. The property has received excellent ratings for its location, cleanliness and overall experience.
This 2-bedroom house, spanning 100 square metres, comfortably accommodates up to 4 guests. Guests can enjoy panoramic city views from the private balcony, relax in the garden, or prepare meals in the fully equipped kitchen.
Pienzalettings - Pienza
9.5 281 reviews
Pienza
2 1
NZ$279/nighttotal: NZ$837 (3 )

Pienzalettings

apartment - Pienza
This Pienza apartment is located in the town centre, just a short walk from the Duomo and Piazza del Popolo, and 45 kilometres from Mount Amiata. The property has received excellent ratings for location, cleanliness, and overall user experience.
The accommodation has a private bathroom, a kitchen with a fridge, freezer, and microwave, and a terrace or balcony. Guests can enjoy a garden, parking, and free Wi-Fi, as well as the option to dine al fresco.
Capanne Di Sopra - Pienza
Pienza
2 3
NZ$1460/nightfor 1 night

Capanne Di Sopra

house - Torrita di Siena
This detached villa in Capanne di Sopra, Montefollonico, is located 14.3 kilometres from Montepulciano Terme and 24.1 kilometres from Bagno Vignoni, with Bagni San Filippo a further 37 kilometres away.
This pet-friendly property accommodates up to 12 guests across 3 bedrooms, offering free WiFi, private parking, a dishwasher, and access to a garden, with a 10:00 AM check-out.

Best pet friendly Pienza holiday rentals

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

Lacasadititti - Pienza
9.7 23 reviews
Pienza
2 1
NZ$203/nightfor 1 night

Lacasadititti

apartment - Chianciano Terme
LaCasaDiTitti is a one-bedroom apartment in Chianciano Terme, conveniently located near Montepulciano Terme (5.6km), Bagno Vignoni (22.5km), and Bagni San Filippo (24km), offering easy access to these popular thermal spa towns.
This 50-square-metre flat features a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, parking, and sleeps up to three guests, perfect for a relaxing Tuscan getaway.
Le Sorbelle D'orcia - Pienza
9.5 153 reviews
Pienza
2 2
NZ$1085/nighttotal: NZ$2170 (2 )

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.
A Casa Di Gabri,  Accoglienza E Semplicità - Pienza
10 15 reviews
Pienza
2 3
NZ$352/nighttotal: NZ$2112 (6 )

A Casa Di Gabri, Accoglienza E Semplicità

apartment - Torrita di Siena
This detached villa near Montefollonico, Siena province, offers easy access to Pienza (5km), Montepulciano (7km), and Montalcino (20km), nestled near hiking trails including routes for L'Eroica and the Via Francigena.
The two-bedroom, two-bathroom property sleeps five, boasting a private garden, fully equipped kitchen with dishwasher, and excellent guest reviews, making it ideal for families exploring Tuscany.
Casa Vittorio - Pienza
10 5 reviews
Pienza
2 1
NZ$154/nightfor 1 night

Casa Vittorio

house - Montepulciano
This centrally located flat in Montepulciano offers immediate access to all local attractions, with major landmarks and tourist spots within easy walking distance for convenient sightseeing.
This one-bedroom flat accommodates up to four guests and features essential amenities including kitchen facilities, air conditioning, and internet, making it ideal for groups exploring the town's culture and historical sites.
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