Holiday Rentals in Pienza

114 available vacation rental offers

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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

Il Casone - Pienza
9.4 81 reviews

Il Casone

apartment, Montalcino
This two-bedroom apartment is situated in Montisi, a peaceful village just 15 miles from Bagno Vignoni and 16 miles from Montepulciano Terme, offering a tranquil escape from the bustling crowds of Montalcino. The property has received excellent ratings for cleanliness, location and overall user experience.
The self-catering apartment is spread over 130 square metres and features a fully equipped kitchen with a dishwasher, a comfortable living area, and a private bathroom. Guests can enjoy free Wi-Fi, parking, and a private entrance, as well as bed linen and towels.
Molino Della Tuoma - Pienza
8.6 10 reviews

Molino Della Tuoma

apartment, San Quirico d'Orcia
Molino della Tuoma, a self-catering apartment in San Quirico d’Orcia, enjoys a tranquil setting near the river, 42km from Mount Amiata and 43km from Siena's Piazza del Campo.
This five-guest property boasts a private garden, terrace, jacuzzi, and spa, plus a fully equipped kitchenette, washing machine, and free Wi-Fi and parking.
Comodo Appartamento Centrale Dimora Delle Mura - Pienza
9.9 124 reviews

Comodo Appartamento Centrale Dimora Delle Mura

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.
Villa ∙ 12 Bedrooms ∙ 24 Guests - Pienza
10 1 review

Villa ∙ 12 Bedrooms ∙ 24 Guests

house, Montepulciano
Villa Cicolina, near Montepulciano in the Tuscan countryside, offers a luxurious stay within easy reach of the town's attractions.
This 18th-century villa and its two annexes provide spacious accommodation for up to 24 guests across 12 bedrooms and 11 bathrooms, boasting a private pool with hydromassage, a professional kitchen, and three self-contained apartments with kitchenettes and fireplaces.

Best Pienza holiday rentals with parking

Maria Gabriella Home - Pienza
No reviews

Maria Gabriella Home

apartment, Pienza
This property, comprising a house and cottage, is located in Monticchiello, a village 5 kilometres from Pienza, offering a base for exploring the Val d'Orcia UNESCO World Heritage site and its picturesque villages.
The expansive 400 square metre estate accommodates up to six guests across three air-conditioned bedrooms, each with a private bathroom, and features a kitchen equipped with a fridge, microwave, and dishwasher, alongside on-site parking and a terrace for shared or private outdoor enjoyment.
Val D'orcia Nel Borgo - Pienza
9.2 167 reviews

Val D'orcia Nel Borgo

apartment, Castiglione d'Orcia
This three-bedroom apartment is situated in Castiglione d'Orcia, just a short drive from the famous thermal baths of Bagno Vignoni and within easy reach of other attractions like Bagni San Filippo and Montepulciano Terme. The property has received excellent ratings for its location, cleanliness and overall experience.
The spacious apartment, covering 85 square metres, comfortably accommodates up to eight guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, Wi-Fi and parking, as well as access to a tennis court and nearby skiing opportunities.
Wonderful Private Villa For 10 People With Wifi, Hot Tub, A/c, Tv And Patio - Pienza
No reviews

Wonderful Private Villa For 10 People With Wifi, Hot Tub, A/c, Tv And Patio

house, Montepulciano
This villa is situated 2 kilometres from Montepulciano, within the renowned Val D'Orcia region, and is 34 kilometres from Montalcino.
Offering 300 square metres of space for up to ten guests, this property features four bedrooms, three bathrooms, air conditioning, a private swimming pool, and Wi-Fi, with a well-equipped kitchen ideal for preparing meals.
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 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

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza
Farm listing for up to 3 people. You will be in Pienza.
Facilities and services include air conditioning, a garden and a washing machine. Take advantage of the terrace in this accommodation!
Agriturismo Il Fienile - Pienza
9.0 311 reviews

Agriturismo Il Fienile

house, Montepulciano
Agriturismo Il Fienile, a farmhouse offering self-catering apartments, is situated in the Tuscan countryside, 1.9km from Montepulciano, providing easy access to the historic centre and local wineries.
This family-friendly property features a swimming pool, gardens with free access to produce, covered parking, and barbecue facilities, all within a fully enclosed complex.
15 Min Da Montepulciano - Villa Chiara - Pienza
8.4 39 reviews

15 Min Da Montepulciano - Villa Chiara

apartment, Torrita di Siena
This three-bedroom, two-bathroom apartment in Montefollonico, a peaceful district 15 minutes' drive (approx. 24km) from Montepulciano, offers easy access to Tuscan hill towns and thermal baths.
The 120 square metre property sleeps 11, features a well-equipped kitchen, terrace, garden, parking, and Wi-Fi, plus a baby safety gate.
Agriturismo Il Casato - Il Torchio - Pienza
9.4 47 reviews

Agriturismo Il Casato - Il Torchio

farm, Pienza
Agriturismo il casato - il torchio is located in Pienza, just 5.4km from the thermal baths of Bagno Vignoni and 43km from Mount Amiata, offering a peaceful escape in the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom farmhouse spans 70 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, free Wi-Fi, and parking, plus table tennis, and opportunities for cycling and hiking in the surrounding area.

Best pet friendly Pienza holiday rentals

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

Agriturismo Palazzi Del Papa - Pienza
9.5 260 reviews

Agriturismo Palazzi Del Papa

farm, Pienza
Agriturismo Palazzi del Papa is located in the Lucciola Bella Nature Reserve, 15 kilometres from both Pienza and Montepulciano, offering a tranquil escape in the Tuscan countryside. The farm has excellent user, location, and cleanliness ratings.
The accommodation features terracotta floors, wood-beamed ceilings, and comfortable lounge areas. Guests can enjoy an outdoor pool, a garden, a restaurant serving farm-fresh meals, and the opportunity to sample the farm's own Orcia DOC wine and extra-virgin olive oil.
Casa Meloni 1 - Pienza
10 1 review

Casa Meloni 1

apartment, Castiglione d'Orcia
Casa Meloni 1, an apartment in Castiglione d'Orcia, is located near Mount Amiata (32 km), Parco dei Mulini (5.9 km), and Bagni San Filippo (17.7 km).
This 55 square metre flat sleeps up to three guests, offering one bedroom, one bathroom, a fully equipped kitchen, air conditioning, and a spacious terrace, with complimentary WiFi and parking provided.
Salcheto Winehouse - Pienza
9.4 1959 reviews

Salcheto Winehouse

farm, Montepulciano
Salcheto Winehouse is a vineyard farm located just a short 3.7-mile drive from the historic town of Montepulciano, offering a peaceful escape surrounded by rolling Tuscan hills. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farm offers a range of accommodation options, from stylish rooms to spacious apartments, all featuring modern amenities and private outdoor spaces. Guests can enjoy a variety of activities on-site, including wine tastings, exploring the traditional wine cellar, and relaxing in the heated outdoor hot tub.
La Falegnameria - Pienza
9.6 27 reviews

La Falegnameria

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.
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