Holiday Rentals in Pienza

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Pienza holiday rentals
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69 Holiday Rentals and Airbnb in Pienza

Casa Con Giardino  “Villa Emma” - Pienza
9.9 27 reviews
Pienza
10/07 – 12/07
NZ$404/nighttotal: NZ$808 (2 )

Casa Con Giardino “Villa Emma”

1 2
apartment, Pienza
This Pienza apartment is conveniently located near the town centre, offering easy access to shops and restaurants, and is within easy walking distance of Pienza's historic Piazza Pio II.
The self-catering property features a fully equipped kitchen, a double bedroom, a living room with a sofa bed sleeping four, a private garden, free Wi-Fi, and parking; Tuscan cooking classes and wine tasting are optionally available.
Agriturismo Il Macchione - Pienza
9.4 1219 reviews
Pienza
09/07 – 10/07
NZ$802/nightfor 1 night

Agriturismo Il Macchione

1 2
house, Pienza
This 18th-century farmhouse is located just 0.9 miles outside of Pienza, overlooking the stunning Val d'Orcia Natural Park, offering a secluded and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse features a spacious terrace with a swimming pool and hydromassage area, perfect for relaxing and enjoying the beautiful surroundings. Guests can also enjoy a range of amenities, including a fitness center, tennis court, and a children's playground, as well as a buffet breakfast and BBQ facilities.
Agriturismo Podere San Gregorio - Pienza
9.3 470 reviews
Pienza
04/07 – 12/07
NZ$227/nighttotal: NZ$1816 (8 )

Agriturismo Podere San Gregorio

1 2
farm, Pienza
Agriturismo Podere San Gregorio is a restored farmhouse located just a short walk from the centre of Pienza, a charming medieval town in the heart of Tuscany. It is also within easy reach of other popular destinations like Montepulciano and Siena. The property has received excellent ratings for its location, cleanliness and overall experience.
The farmhouse offers comfortable accommodation with a private garden and free BBQ facilities. Guests can enjoy a delicious breakfast basket delivered to their room each morning and have the option of purchasing locally produced olive oil and wine.
Agriturismo I Roseti - Pienza
9.7 362 reviews
Pienza
09/07 – 10/07
NZ$288/nightfor 1 night

Agriturismo I Roseti

1 2
farm, Montepulciano
Agriturismo I Roseti is located in the Tuscan hills, just 14 kilometres from Bagno Vignoni and 43 kilometres from Arezzo, offering stunning views of the surrounding olive groves and orchards. It boasts excellent user, location and cleanliness ratings.
The property is a one-bedroom farmhouse with a floor area of 50 square metres, featuring a kitchenette, a private bathroom, and a living room with a flat-screen TV. Guests can enjoy a welcome basket filled with local treats, BBQ facilities, and free WiFi, as well as a terrace, garden, and parking.
La Falegnameria - Pienza
9.6 19 reviews
Pienza
07/09 – 18/09
NZ$172/nighttotal: NZ$1892 (11 )

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.
La Corte Antica Appartamento" La Loggia" - Pienza
9.9 29 reviews
Pienza
05/08 – 08/08
NZ$575/nighttotal: NZ$1725 (3 )

La Corte Antica Appartamento" La Loggia"

1 3
apartment, Pienza
This two-bedroom apartment is situated in the historic centre of Pienza, just a short walk from the famous Piazza Pio II, offering easy access to the town's main attractions.
The self-catering property features a fully equipped kitchen, two bathrooms, a private courtyard, and free Wi-Fi, making it perfect for families or groups of up to four people.
Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
Pienza
10/08 – 11/08
NZ$298/nightfor 1 night

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

2 2
farm, Pienza
Farm rental for up to 3 guests. This accommodation is located in Pienza.
Facilities and services include a barbecue, a washing machine and a garden. This accommodation also has a terrace!
Tenuta Santo Pietro - Pienza
9.3 706 reviews
Pienza
29/08 – 02/09
NZ$705/nighttotal: NZ$2820 (4 )

Tenuta Santo Pietro

1 2
farm, Pienza
Tenuta Santo Pietro is a working farm located just three miles from the historic town of Pienza, nestled in the Tuscan countryside. The farm enjoys excellent ratings for its location, cleanliness, and overall experience.
The farmhouse dates back to the 13th century and has been beautifully restored, featuring terracotta floors and exposed wooden beams. Guests can enjoy a swimming pool, a restaurant serving traditional Tuscan cuisine, and a range of activities including wine and olive oil tastings, as well as exploring the peaceful gardens.
Luxury Historic Estate With Panoramic Tuscan Views - Pienza
Pienza
16/08 – 19/08
NZ$2606/nighttotal: NZ$7818 (3 )

Luxury Historic Estate With Panoramic Tuscan Views

1 13
house, Sinalunga
This historic luxury villa, offering complete privacy, is located in the Tuscan countryside near Sinalunga, providing panoramic views of local villages.
This exclusive residence accommodates up to 16 guests, featuring 7 bathrooms, a kitchen, air conditioning, and internet, with pets welcome, ensuring a comfortable and authentic Tuscan experience.
Casa Aldobrandesca - Pienza
9.5 57 reviews
Pienza
27/06 – 28/06
NZ$383/nightfor 1 night

Casa Aldobrandesca

2 4
house, Castiglione d'Orcia
Casa Aldobrandesca in Castiglione d’Orcia offers a convenient base for exploring Tuscany, situated 5.1km from Bagno Vignoni, 17.7km from Bagni San Filippo, and 27.4km from Montepulciano Terme.
This 65 square metre holiday home sleeps seven guests and features two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, free Wi-Fi, and a tennis court; plus packed lunches are provided for day trips.
Agriturismo Il Casato Mag-il Vaglio - Pienza
9.8 9 reviews
Pienza
09/08 – 10/08
NZ$1123/nightfor 1 night

Agriturismo Il Casato Mag-il Vaglio

2 4
gîte, Pienza
Agriturismo Il Casato Mag-il Vaglio is situated near Pienza, just 7km from the Vitaleta Chapel, 9km from the House of the Gladiators, and 10km from Bagno Vignoni, offering stunning mountain views in the heart of the Val d'Orcia. This charming cottage provides a comfortable escape for up to four guests, featuring two bedrooms and a well-equipped kitchen. The property offers a range of amenities including air conditioning, a private garden, parking, and a shared terrace with a barbecue, as well as access to guided wine cellar tours and tastings, electric bike and vintage car rentals, and a delicious breakfast option.
Il Saragio - Pienza
9.6 43 reviews
Pienza
27/06 – 29/06
NZ$199/nighttotal: NZ$398 (2 )

Il Saragio

1 2
house, Montepulciano
Il Saragio, a self-catering property in the Abbadia di Montepulciano district, is situated 14.6 kilometres from Montepulciano Terme and 34 kilometres from Bagno Vignoni, both renowned for their thermal spas.
This 70-square-metre house features one bedroom, one bathroom, a fully equipped kitchen, private parking, Wi-Fi, a terrace, garden, barbecue, and bike/car rental, sleeping up to two guests and offering a private and secluded stay.

Best family friendly Pienza holiday rentals

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

Charming Gateway To Tuscany - The Scenic House Of The Lamps In Val D'orcia - Pienza
10 91 reviews
Pienza
04/07 – 12/07
NZ$187/nighttotal: NZ$1496 (8 )

Charming Gateway To Tuscany - The Scenic House Of The Lamps In Val D'orcia

1 2
apartment, San Quirico d'Orcia
This charming apartment is located in the heart of San Quirico d'Orcia, a UNESCO World Heritage Site, just a short walk from the main square and its historic attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment offers one bedroom and one bathroom, with a total floor area of 47 square metres, comfortably accommodating up to four guests. It comes equipped with a fully equipped kitchen, air conditioning, free parking, and fast Wi-Fi for a pleasant and comfortable stay.
Agriturismo Belagaggio - Pienza
9.4 550 reviews
Pienza
21/07 – 22/07
NZ$507/nightfor 1 night

Agriturismo Belagaggio

1 2
farm, Torrita di Siena
Agriturismo Belagaggio is located in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering stunning views of the surrounding countryside. The property has received excellent ratings for its location, cleanliness and overall experience.
This recently renovated farmhouse offers comfortable accommodation with a range of amenities including a swimming pool, jacuzzi, and terrace. Guests can enjoy a restaurant serving local cuisine, a spa, and a variety of activities such as cycling and hiking.
Gioconda Suite - Podere Casa Rossa à Pienza - Pienza
9.8 32 reviews
Pienza
09/07 – 10/07
NZ$507/nightfor 1 night

Gioconda Suite - Podere Casa Rossa à Pienza

1 2
gîte, Pienza
This Pienza holiday cottage, located in the Val d'Orcia, is less than 2km from Pienza's historic centre, offering stunning views of the countryside.
Sleeping four guests, this self-catering property features two bedrooms, a fully equipped kitchen including a fridge-freezer and microwave, air conditioning, a private garden with gazebo, covered parking for up to three cars, and self check-in.
L’ Angolo Di Pienza - Pienza
8.7 261 reviews
Pienza
21/07 – 23/07
NZ$216/nighttotal: NZ$432 (2 )

L’ Angolo Di Pienza

1 2
apartment, Pienza
L’ANGOLO DI PIENZA is located in the charming town of Pienza, just 45km from Mount Amiata, surrounded by the beautiful Val d’Orcia, a UNESCO World Heritage Site. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom flat offers a comfortable living space with a sofa, seating area, and a flat-screen TV. It also features a well-equipped kitchen, a private bathroom, and a swimming pool. Guests can enjoy the peace and quiet of Pienza, explore the nearby attractions, and relax in the beautiful surroundings.

Best Pienza holiday rentals with parking

Casa Del Capitano Rocca D'orcia - Pienza
9.5 50 reviews
Pienza
27/06 – 04/07
NZ$187/nighttotal: NZ$1309 (7 )

Casa Del Capitano Rocca D'orcia

1 2
apartment, Castiglione d'Orcia
This charming apartment is situated in the hamlet of Rocca d'Orcia, just a short 2-kilometre drive from Castiglione d'Orcia, offering a peaceful escape in the heart of the UNESCO-protected Valdorcia Park. This property has consistently received excellent reviews for its location, cleanliness, and overall experience.
The apartment features one bedroom and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests will enjoy access to a fully equipped kitchen, a terrace, a garden, and parking, ensuring a relaxing and enjoyable stay.
La Falegnameria - Pienza
9.3 35 reviews
Pienza
10/08 – 11/08
NZ$282/nightfor 1 night

La Falegnameria

1 2
apartment, Castiglione d'Orcia
La Falegnameria apartment in Castiglione d’Orcia is conveniently located a short distance (5.5km) from Bagno Vignoni's thermal baths and 18km from Bagni San Filippo, offering easy access to these popular spa towns.
This 50 square metre flat features one bedroom, one bathroom, and can accommodate up to seven guests, boasting a private terrace, fully equipped kitchenette, free Wi-Fi, and parking.
Pienzalettings - Pienza
9.7 276 reviews
Pienza
30/09 – 03/10
NZ$419/nighttotal: NZ$1257 (3 )

Pienzalettings

1 4
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.
Agriturismo Bagnolo - Pienza
9.0 235 reviews
Pienza
03/07 – 05/07
NZ$247/nighttotal: NZ$494 (2 )

Agriturismo Bagnolo

1 2
farm, Pienza
Agriturismo Bagnolo is a farm stay situated in the Tuscan countryside, just 4km from the historic town of Pienza, and within easy reach of Montepulciano and Chianciano Terme. This highly-rated property boasts excellent user, location, and cleanliness ratings.
The farm offers a choice of rooms and apartments, accommodating up to two guests. Enjoy a range of amenities including a jacuzzi, terrace, garden, and parking, as well as the opportunity to participate in the production of oil and cheese, and witness the farm's animals firsthand.

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.

Destinations nearby

Best Pienza holiday rentals with a balcony

Torre Appartamento Con Vista - Pienza
9.7 163 reviews
Pienza
16/07 – 19/07
NZ$306/nighttotal: NZ$918 (3 )

Torre Appartamento Con Vista

1 2
apartment, Pienza
This one-bedroom apartment is situated in the peaceful village of Monticchiello, just 10.5 kilometres from Montepulciano Terme and 13.2 kilometres from Bagno Vignoni. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably accommodates two guests and features a well-equipped kitchen with a fridge and dishwasher, as well as a terrace, garden, spa, restaurant, fitness centre, and parking. Guests can also enjoy on-site bike rentals, free Wi-Fi, and a traditional Tuscan design.
Farmhouse With Pool, Views - Pienza
9.2 625 reviews
Pienza
27/06 – 29/06
NZ$930/nighttotal: NZ$1860 (2 )

Farmhouse With Pool, Views

3 2
house, Castiglione d'Orcia
Podere Il Tigliolo is a countryside retreat located 5.6 miles from the centre of Castiglione d'Orcia, with Lake Castiglione reachable within a one-hour drive. The property has received excellent ratings for cleanliness and user experience, while the location is rated very good.
The apartments feature exposed-beam ceilings, offering a charming and authentic Tuscan experience. Guests can enjoy refreshing dips in the private outdoor pool, relax in the garden with BBQ facilities, and stay connected with complimentary Wi-Fi access in public areas.
Wonderful Villa In Tuscany - Villa Gaeta - Pienza
Pienza
21/07 – 22/07
NZ$3185/nightfor 1 night

Wonderful Villa In Tuscany - Villa Gaeta

5 2
apartment, Torrita di Siena
This five-bedroom, five-bathroom villa is situated in Torrita di Siena, Tuscany, less than 0.1km from Val di Chiana and within 10km of Triacca Winery, Pienza's historic centre, and other local attractions.
The 300 square metre property boasts a private pool, jacuzzi, and extensive outdoor space including a garden, terrace, and parking, comfortably accommodating up to 12 guests and offering a fully equipped kitchen and air conditioning.
Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi - Pienza
Pienza
09/07 – 10/07
NZ$2452/nightfor 1 night

Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi

3 2
house, Trequanda
This detached villa is located in Trequanda, a Tuscan town with convenient access to Siena (60 kilometres), Florence (100 kilometres), Pienza (20 kilometres), and Montepulciano (15 kilometres).
This 156 square meter, two-storey holiday home offers three bedrooms, three bathrooms, and accommodates up to six guests, featuring Wi-Fi, air conditioning, a dishwasher, a private balcony, and access to a shared swimming pool.

Best pet friendly Pienza holiday rentals

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

Agriturismo Il Casalino - Pienza
9.5 1587 reviews
Pienza
21/07 – 22/07
NZ$453/nightfor 1 night

Agriturismo Il Casalino

1 2
farm, Pienza
Agriturismo Il Casalino is a 19th-century farmhouse located in Pienza, a UNESCO World Heritage site, just 39 kilometres from Siena and 47 kilometres from Arezzo, offering stunning views of the Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers independent apartments with a rustic interior design, each with its own entrance. Guests can enjoy a range of amenities including a terrace with panoramic views, a garden, free parking, WiFi, and the option to rent bikes to explore the surrounding area.
Primo Maggio - Pienza
Pienza
27/06 – 28/06
NZ$845/nightfor 1 night

Primo Maggio

3 4
apartment, Castiglione d'Orcia
This recently renovated apartment in Castiglione d'Orcia offers breathtaking panoramic views of the Val d'Orcia and Monte Amiata, with exceptional stargazing opportunities.
Accommodating up to six guests, this residence features three en-suite double bedrooms, a spacious living area, a private garden, and a modern kitchen equipped with a fridge, freezer, and dishwasher, with a shared laundry facility located 100 meters away.
90 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
Pienza
25/07 – 30/07
NZ$515/nighttotal: NZ$2575 (5 )

90 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 2
house, Torrita di Siena
This secluded rural property, offering a tranquil escape, is situated in a panoramic location near Montefollonico (1.3 km) and Montepulciano (7 km), boasting spectacular views of the Montepulciano valley, San Biagio temple, Monte Amiata, and the Val d'Orcia hills.
This holiday home, spanning 90 square meters and accommodating up to six guests, features two independent stone houses, including the restored 17th-century Casa MULINELLO with a living room, two fireplaces, and two panoramic terraces, along with a kitchen equipped with a fridge and dishwasher, and is pet and family friendly with internet and parking.
Il Borghetto -Oliviera Townhouse - Pienza
9.9 36 reviews
Pienza
27/06 – 29/06
NZ$257/nighttotal: NZ$514 (2 )

Il Borghetto -Oliviera Townhouse

1 2
apartment, Montalcino
This Montalcino holiday apartment, a former olive oil mill near San Giovanni d'Asso's medieval castle (walking distance, precise distance unspecified), offers a unique historical setting within the Val d'Orcia region.
The first-floor flat comprises a living area with kitchen, one double bedroom, one bathroom, and accommodates two guests, featuring air conditioning, Wi-Fi, and pet-friendly access; the official registration number is IT052037B462AH4700.
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