Compare Vacation Rentals & Airbnb in Pienza

114 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Pienza vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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

165 M² Farmhouse ∙ 6 Bedrooms ∙ 11 Guests - Pienza
9.8 48 reviews

165 M² Farmhouse ∙ 6 Bedrooms ∙ 11 Guests

farm, Pienza
Farm listing for 11 people with an excellent rating of 98% based on 48 reviews. This accommodation is located in Pienza.
Services and facilities: a washing machine, a ping pong table and a kitchen. Take advantage of the Free Parking with this accommodation.
Spacious Luxury Stay In Pienza | 3br 3ba - Pienza
10 91 reviews

Spacious Luxury Stay In Pienza | 3br 3ba

apartment, Pienza
This three-bedroom, three-bathroom apartment in Pienza's historic centre is steps from Piazza Pio II and a major church.
The 6-guest property boasts a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, and self check-in via key box.
A Casa Di Gabri - Pienza
9.5 10 reviews

A Casa Di Gabri

house, Torrita di Siena
This charming holiday home is located in Montefollonico, a peaceful village just a short drive from Torrita di Siena, offering easy access to the town's shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house provides ample space for up to five guests, with three bedrooms, two bathrooms, and a total floor area of 100 square metres. Guests can enjoy a fully equipped kitchen, a relaxing garden, and a terrace for outdoor dining, as well as free Wi-Fi access throughout the property.
Nonna Mari - Pienza
9.1 34 reviews

Nonna Mari

apartment, Montepulciano
This apartment is situated in a peaceful location, just 5.5 kilometres from Montepulciano Terme and within easy reach of other thermal baths such as Bagno Vignoni (21 kilometres) and Bagni San Filippo (27 kilometres). It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, offering ample space for six guests across 80 square metres. Enjoy modern amenities such as a flat-screen TV and free Wi-Fi, and take advantage of its proximity to the picturesque village of Pienza (16 kilometres) and the historic city of Siena (48 kilometres).

Best Pienza vacation rentals with parking

Podere Santaadele - Pienza
8.5 139 reviews

Podere Santaadele

farm, Montepulciano
Podere SantaAdele is a farm located 7km from the spa town of Terme di Montepulciano, set in the peaceful Tuscan countryside. It has consistently received very good ratings for its location, cleanliness, and overall experience.
The farm offers a range of comfortable rooms and spacious apartments, catering to different needs. Guests can enjoy a seasonal outdoor pool, a garden with barbecue facilities, free Wi-Fi, and parking.
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.
Casa L Oleandro - Pienza
9.0 20 reviews

Casa L Oleandro

apartment, Montalcino
This apartment in Montalcino is located in a quiet area, offering easy access to the historic centre and the renowned Brunello wine region, approximately 1.5 kilometres away.
This 50 square metre flat, suitable for up to 7 guests, features one bedroom, one bathroom, a fully equipped kitchen, free WiFi, air conditioning, and complimentary private parking.
Monastero Sant'anna In Camprena - Pienza
9.6 427 reviews

Monastero Sant'anna In Camprena

farm, Pienza
Fattoria Monastero Sant'Anna in Camprena is located in the Tuscan countryside, just 19 kilometres from Bagno Vignoni and 23 kilometres from Montepulciano Terme, offering a peaceful escape from the hustle and bustle of Pienza. This farm stay has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The property features a charming restaurant, a garden and a terrace, providing ample space for relaxing and enjoying the beautiful surroundings. This farm stay can accommodate up to two guests in its comfortable and modern accommodation, which includes air conditioning, a private bathroom, a fridge, a microwave oven and free Wi-Fi.

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

Cosy Apartment With A/c, Wifi, Pool, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano - Pienza
No reviews

Cosy Apartment With A/c, Wifi, Pool, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano

farm, Trequanda
This farm stay is situated in the Orcia Valley, 10 kilometres from Torrita di Siena and 16 kilometres from Montepulciano, offering a base for exploring this renowned tourist district.
This property provides 14 apartments across 220 square metres, accommodating up to 6 guests with 3 bedrooms and 3 bathrooms, and features a shared swimming pool, WiFi, and on-site cooking lessons.
Chianciano Lettings -Room And Apartments- - Pienza
9.5 240 reviews

Chianciano Lettings -Room And Apartments-

apartment, Chianciano Terme
This apartment is situated in Chianciano Terme, a short distance from the thermal baths and within easy reach of the charming villages of Bagno Vignoni and Bagni San Filippo. The accommodation has received excellent ratings for location, cleanliness and user satisfaction.
The two-bedroom apartment provides a comfortable and spacious living area, ideal for families or groups. Guests can enjoy the convenience of a fully equipped kitchen, a private balcony and a peaceful garden, as well as free parking and Wi-Fi.
Villa ∙ 7 Bedrooms ∙ 14 Guests - Pienza
No reviews

Villa ∙ 7 Bedrooms ∙ 14 Guests

house, Montepulciano
This expansive villa is located in a district of Montepulciano providing easy access to the town's historic centre, a UNESCO World Heritage site renowned for its Renaissance architecture.
Offering accommodation for up to 14 guests, this property features seven bedrooms, multiple well-equipped kitchens including one with seating for 20, a swimming pool, Jacuzzi, air conditioning, and WIFI throughout, with six bedrooms boasting ensuite bathrooms and several with whirlpool bathtubs.
195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests - Pienza
10 8 reviews

195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Pienza
This spacious 195 square metre holiday home is situated in Monticchiello, a medieval village in the Val d'Orcia, a UNESCO World Heritage site, a short drive from Pienza and offering proximity to the unique 'poor theatre' tradition.
The three-bedroom, two-bathroom property boasts a fireplace, terrace, garden, parking, and features including a dishwasher and air conditioning, comfortably sleeping eight guests and providing easy access to Lake Trasimeno and other Tuscan attractions.

Best pet friendly Pienza vacation rentals

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

Casa Dolce Casa - Pienza
10 2 reviews

Casa Dolce Casa

house, Montepulciano
This two-bedroom flat in Montepulciano offers unparalleled convenience, situated directly opposite a supermarket and within immediate walking distance of bars, cafes, and traditional eateries, making it ideal for exploring the town and its surroundings without a car.
This residence, accommodating up to five guests, features two bathrooms, air conditioning, and a kitchen, with bicycle and e-bike rental available nearby for easy access to local attractions, facilitating spontaneous outings and daily needs.
Agriturismo Selvoli - La Chiocciola - Pienza
9.9 35 reviews

Agriturismo Selvoli - La Chiocciola

gîte, Pienza
This three-bedroom self-catering apartment, located in the Val d'Orcia, is 5km from both Pienza and Bagno Vignoni.
The property boasts a private outdoor space with barbecue, access to a shared swimming pool (June-September), and sleeps six guests in its three en-suite bedrooms, featuring a traditional fireplace and fully equipped kitchen including a dishwasher.
Podere Spagliarda - Pienza
10 1 review

Podere Spagliarda

house, San Quirico d'Orcia
Podere Spagliarda, a four-bedroom holiday home in San Quirico d’Orcia, Val d’Orcia, offers easy access to other towns and attractions in the area.
This self-catering property sleeps up to twelve guests, boasting a private garden, swimming pool access, four bathrooms, a fully equipped kitchen including a dishwasher, and ample parking for four cars.
70 M² House ∙ 1 Bedroom ∙ 2 Guests - Pienza
9.1 11 reviews

70 M² House ∙ 1 Bedroom ∙ 2 Guests

house, San Quirico d'Orcia
This Tuscan holiday home is situated near San Quirico d’Orcia, a short distance from the Renaissance garden at the Church of Santa Maria Assunta.
The 70 square metre property offers one bedroom, two bathrooms, sleeps four, and includes a kitchen with fridge and dishwasher, plus a garden, parking, and internet access.
©2026 cozycozy.com