Compare Vacation Rentals & Airbnb in Pienza

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Pienza vacation rentals
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114 Rentals and Airbnb in Pienza

Best family friendly Pienza vacation rentals

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

Sunflower - Pienza
8.9 100 reviews

Sunflower

apartment, San Quirico d'Orcia
The Sunflower apartment is situated in San Quirico d'Orcia, a village in Tuscany, 40 kilometres from Mount Amiata and 45 kilometres from Siena's Piazza del Campo.
This 90 square metre self-catering property has two bedrooms, a living room, a fully equipped kitchen and a private garden and terrace, perfect for enjoying the Tuscan sunshine.
Villa Limone - 3 Bedroom Villa In Tuscany - Pienza
No reviews

Villa Limone - 3 Bedroom Villa In Tuscany

apartment, Trequanda
This Tuscan villa is situated in Trequanda, offering proximity to cultural sites such as the Artemisia Gallery and Palazzo Borgia, and is located within 10 kilometres of local wineries including Triacca Winery and Enoteca Di Ghino.
This spacious 156 square metre villa accommodates up to six guests across three bedrooms and three bathrooms, featuring a fully equipped kitchen, air conditioning, Wi-Fi, private garden, and shared resort facilities including a swimming pool.
Agriturismo Poggio Tobruk - Pienza
9.5 602 reviews

Agriturismo Poggio Tobruk

farm, Pienza
Agriturismo Poggio Tobruk is situated in the Val d'Orcia Park, a UNESCO World Heritage Site, just 10 kilometres from the historic town of Pienza, offering stunning views of the olive groves and Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers self-catering apartments with a fully equipped kitchenette, a spacious dining room for enjoying traditional Tuscan cuisine, and a terrace or balcony for relaxing. Guests can enjoy a range of amenities including a tennis court, a garden, and free parking, as well as purchase authentic olive oil produced directly on the farm.
Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.5 64 reviews

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Pienza
Farm for 5 guests with an excellent rating of 95% based on 64 reviews. Your accommodation will be based in Pienza.
Services and facilities: a fridge, a restaurant and a garden. Pets are welcome in this accommodation.

Best Pienza vacation rentals with parking

Poggio Paradiso Resort & Spa - Pienza
9.4 143 reviews

Poggio Paradiso Resort & Spa

resort, Torrita di Siena
Poggio Paradiso Resort & Spa is located in Montefollonico, a charming village just 18 kilometres from Montepulciano Terme and 50 kilometres from Piazza Grande. The resort has consistently received excellent ratings from guests for its location, cleanliness, and overall experience.
The resort offers a range of comfortable rooms with private bathrooms and some featuring balconies. Guests can enjoy a variety of amenities, including a swimming pool, a spa, a restaurant, and a bar, as well as activities like cycling and exploring the surrounding Tuscan countryside.
150 M² House ∙ 4 Bedrooms ∙ 8 Guests - Pienza
8.1 10 reviews

150 M² House ∙ 4 Bedrooms ∙ 8 Guests

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.
Torre Appartamento Con Vista - Pienza
9.7 166 reviews

Torre Appartamento Con Vista

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.
La Pineta Gelsomino  Monolocale In Val Dorcia - Pienza
9.6 217 reviews

La Pineta Gelsomino Monolocale In Val Dorcia

apartment, Castiglione d'Orcia
This ground-floor studio apartment in Castiglione d’Orcia is conveniently located near the historic centre, offering easy access to local amenities and parking.
The self-catering apartment sleeps two guests and features a private garden, ensuite bathroom, a shared garden with gazebo and panoramic views, fridge, and microwave.

Frequently Asked Questions about vacation rentals in Pienza

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

    Pienza is a beautiful town, but if you want to explore beyond its charming streets, you should definitely visit the nearby town of Montepulciano. It's known for its wine and has a stunning Duomo. And, of course, you can't miss the stunning views of the Val d'Orcia, just a short drive away. It's a landscape that's been featured in many films, and it's easy to see why.
  • 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 best walk in Pienza is around the town walls, offering lovely views of the surrounding countryside. If you're feeling energetic, you can cycle to the nearby town of Monticchiello, which is a short, but scenic, ride. The roads are generally quiet, and you'll be rewarded with breathtaking views.
  • 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?

    Pienza is perfect for those who enjoy outdoor activities. You can go hiking in the Val d'Orcia, or try your hand at mountain biking on the trails near the town. There are also plenty of opportunities for horseback riding, and if you're feeling adventurous, you could even try paragliding.
  • 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?

    From Pienza, you can easily reach Siena, a beautiful medieval city, in about an hour by car. You could also visit the charming town of Montalcino, famous for its Brunello wine, or head to the vibrant city of Florence, which is about a two-hour drive.
  • 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?

    Most vacation rentals in Pienza offer basic amenities like a kitchen, bathroom, and Wi-Fi. Many also have a private terrace or balcony, offering stunning views of the countryside. Some might even have a swimming pool, especially if you're renting a villa.
  • 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 the best times to visit Pienza, as the weather is pleasant and the crowds are smaller. You'll experience the beauty of the Val d'Orcia in its full glory, with rolling hills and vineyards bathed in golden light. Avoid the summer months if you don't like intense heat.
  • What are the local dishes in Pienza region?

    Pienza is famous for its pecorino cheese, so you must try it in all its forms, from fresh to aged. You should also indulge in the local pasta dishes, like pici cacio e pepe, and the delicious Tuscan bread, known as schiacciata. And don't forget to try the local wines, especially the Rosso di Montalcino.

Popular destinations

Best Pienza vacation rentals with a balcony

Casa In Chiana - Pienza
10 69 reviews

Casa In Chiana

apartment, Torrita di Siena
Casa in Chiana, a recently renovated apartment in Torrita di Siena, is situated 16km from Montepulciano Terme and 45km from Piazza Grande in Arezzo.
This 50-square-metre self-catering flat offers one bedroom, one bathroom, a private garden, swimming pool, tennis court, free Wi-Fi, and free bikes for exploring the Tuscan countryside, sleeping up to two guests.
Agriturismo La Chiusa Tuscany - Pienza
No reviews

Agriturismo La Chiusa Tuscany

house, Torrita di Siena
This luxurious villa is located in Torrita di Siena, just a short drive from the charming town centre and surrounded by rolling hills with stunning views of Montepulciano and Monte Amiata. The villa is situated in a peaceful and secluded location, perfect for a relaxing getaway.
The villa spans 3716 square metres and can accommodate up to 40 guests in its 18 bedrooms and 18 bathrooms. Guests can enjoy a range of amenities, including a swimming pool, spa, garden, and terrace, as well as activities such as wine tours, mountain biking, and horseback riding.
Sweet Home In Montepulciano Di Olimpia, Three Bedrooms, Bathroom, Kitchen, Wifi, Winery - Pienza
No reviews

Sweet Home In Montepulciano Di Olimpia, Three Bedrooms, Bathroom, Kitchen, Wifi, Winery

apartment, Montepulciano
This spacious flat is located in the central district of Montepulciano, offering walking access to the town's core, including the Civic Museum and Palazzo Avignonesi, and is positioned 500 meters from La Foce.
This 70 square meter residence accommodates up to six guests across two bedrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, and parking, with e-bike and Vespa hire available for exploring the Val di Chiana.
Casa Biagiotti Val D'orcia - Pienza
No reviews

Casa Biagiotti Val D'orcia

apartment, Castiglione d'Orcia
Casa Biagiotti Val d'Orcia, a holiday let in Castiglione d'Orcia, is ideally situated 5.6 kilometres from the thermal springs of Bagno Vignoni, 17.7 kilometres from Bagni San Filippo, and 30.6 kilometres from Mount Amiata.
This 80 square metre apartment accommodates up to seven guests across two bedrooms and two bathrooms, featuring a fully equipped kitchen and complimentary WiFi, with free private parking also provided.

Best pet friendly Pienza vacation rentals

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

Casa Vacanze Oliviera Pienza - Pienza
9.6 22 reviews

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.
La Tresa Country Living - Pienza
9.5 22 reviews

La Tresa Country Living

farm, Montepulciano
La Tresa Country Living is a farm stay located in Montepulciano, offering garden views and convenient access to local attractions.
This pet-friendly, family-friendly accommodation features one bedroom and one bathroom, with complimentary WiFi, private parking, a garden, a terrace, and an outdoor picnic area.
156 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

156 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

house, Trequanda
This spacious two-storey villa apartment in Trequanda provides a tranquil retreat, located a short distance from local attractions.
The accommodation, covering 156 square meters, accommodates up to six guests across three bedrooms and three bathrooms, featuring air conditioning, Wi-Fi, a private balcony, and access to a shared swimming pool, with parking for three vehicles and pet-friendly options available for a fee.
Brunhouse - Pienza
9.1 31 reviews

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.
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