Holiday Rentals in Pienza

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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

Dimora Del Corso Di Montepulciano - Pienza
9.2 527 reviews

Dimora Del Corso Di Montepulciano

apartment, Montepulciano
Dimora Del Corso Di Montepulciano is situated in the historic centre of Montepulciano, just 9.3 miles from the UNESCO-protected town of Pienza. The apartment is highly rated for location, cleanliness, and overall experience.
This one-bedroom apartment offers a comfortable and stylish space for a relaxing stay. Guests can enjoy modern amenities like air conditioning, free Wi-Fi, and a dishwasher, alongside a terrace, a garden, and a swimming pool.
Agriturismo Pascianella Appartamento Bel Tramonto - Pienza
10 5 reviews

Agriturismo Pascianella Appartamento Bel Tramonto

farm, Trequanda
Agriturismo Pascianella Appartamento bel tramonto, near Castelmuzio in Tuscany, offers a peaceful countryside escape approximately 22.5km from Bagno Vignoni and 50km from Piazza Grande.
This two-bedroom, two-bathroom property boasts a 15 square metre floor area, sleeps six guests, and includes a kitchenette with oven and fridge, private parking, Wi-Fi, a garden, barbecue facilities, and a satellite TV.
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.
Agriturismo Palazzo Conti - B - Pienza
8.0 87 reviews

Agriturismo Palazzo Conti - B

farm, San Quirico d'Orcia
Agriturismo Palazzo Conti - B is situated in Pienza, a charming town in the Val d'Orcia, just 22 miles from Siena and 29 miles from Arezzo, making it an ideal base for exploring the Tuscan countryside. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The farm offers comfortable accommodation for up to four guests, with a fully equipped kitchen and a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace or in the garden, and benefit from free Wi-Fi and parking.

Best Pienza holiday rentals with parking

Fattoria Del Colle - Pienza
8.7 298 reviews

Fattoria Del Colle

farm, Trequanda
Fattoria del Colle is a farmhouse located in the Tuscan countryside, 3.5km from Trequanda, 16km from Pienza, and a 35-minute drive from Montepulciano.
This rural retreat offers apartments with kitchenettes, a swimming pool, jacuzzi, sauna, spa, restaurant, tennis court, and features such as a chapel and children's playground; wine and olive oil tasting is also available on-site.
Debby Appartamenti - Pienza
9.3 90 reviews

Debby Appartamenti

apartment, Montepulciano
Debby Appartamenti, a two-bedroom apartment in Montepulciano, is conveniently located 5.8km from Montepulciano Terme, offering easy access to the thermal baths and within easy driving distance of Bagno Vignoni (21km) and Bagni San Filippo (29km).
This self-catering flat features a fully equipped kitchen with fridge and microwave, a private terrace, free Wi-Fi, air conditioning, parking, and a bathroom with bidet and hairdryer; sleeping up to four guests, it’s ideal for exploring Tuscany's thermal areas.
Luxury Historic Estate With Panoramic Tuscan Views - Pienza
No reviews

Luxury Historic Estate With Panoramic Tuscan Views

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.
La Corte Antica Appartamento " Il Chiassino" - Pienza
10 13 reviews

La Corte Antica Appartamento " Il Chiassino"

apartment, Pienza
Il Chiassino apartment is centrally located in Pienza's historic centre, a short walk from Piazza Pio II.
This two-bedroom, two-bathroom flat sleeps three guests, offering a fully equipped kitchen with dishwasher, private parking 0.25km away, and a three-story layout comprising a ground floor kitchen, first-floor single bedroom and bathroom, and a second-floor double bedroom and bathroom.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town with plenty to see. You should definitely visit the Duomo, a stunning example of Renaissance architecture, and the Palazzo Piccolomini, a magnificent palace with a beautiful courtyard. For a stunning view of the Val d'Orcia, head to the Fortezza, a medieval fortress on a hill overlooking the town. If you want to explore the surrounding area, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia, all of which are within a 30-minute drive.
  • 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?

    For walking, you can take a stroll around the historic centre, visiting the main sights. There's also a lovely walk along the Via Cassia, an ancient Roman road that runs through the Val d'Orcia. For cycling, the Val d'Orcia is a great place to explore, with rolling hills and stunning views. You can follow the Via Cassia or head out to the nearby town of Montepulciano for a longer ride.
  • 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 a great place for outdoor activities. You can go hiking in the surrounding hills, go for a swim in the nearby Lake Trasimeno, or play tennis at the local tennis club. There are also several horse riding schools in the area, so you can enjoy a horseback riding tour of the Val d'Orcia.
  • 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 other towns or cities can be easily accessed from Pienza?

    Pienza is well-connected to other towns and cities in Tuscany. You can easily reach Siena, Florence, and Rome by car or train. If you're looking for a day trip, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia.
  • 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?

    Vacation rentals in Pienza typically come with a range of amenities. Most rentals have a kitchen, a bathroom, and a living area. Many also have a private garden or terrace, and some even have a swimming pool. You can find rentals that are perfect for families, couples, or groups of friends.
  • 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?

    The best time to visit Pienza is during the spring or autumn, when the weather is mild and the crowds are smaller. The summer months can be very hot and crowded, but if you don't mind the heat, you can enjoy the many outdoor activities that Pienza has to offer.

Popular destinations

Best Pienza holiday rentals with a balcony

Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany - Pienza
9.6 20 reviews

Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany

house, Pienza
This charming house is located in a peaceful rural setting, just 15 kilometres from Pienza's main attractions, including Piazza delle Sorgenti, Art Studio di Adelina Quadri, and La Foce. It has received excellent reviews from previous guests.
The house spans 400 square metres and comfortably accommodates up to 20 guests. The property features a private pool, a spacious garden, and a barbecue area, perfect for relaxing and enjoying the Tuscan sunshine.
Agriturismo Vergelle - Pienza
9.0 67 reviews

Agriturismo Vergelle

farm, Montalcino
Agriturismo Vergelle is situated in the Crete Senesi, a 30-minute drive from San Quirico d’Orcia and 19 kilometres from the Abbey of Monte Oliveto Maggiore, offering a peaceful escape in the Tuscan countryside. The property consistently receives very good ratings for its location, cleanliness, and overall experience.
The apartments are decorated in a rustic style with wood-beamed ceilings and terracotta floors, creating a charming and authentic Tuscan ambiance. Guests can enjoy a range of amenities including a swimming pool, a garden with BBQ facilities, and a restaurant serving fresh, locally sourced ingredients.
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 La Buca Di Bellugi - Pienza
9.3 191 reviews

Agriturismo La Buca Di Bellugi

farm, San Quirico d'Orcia
Agriturismo La Buca di Belluigi is a charming rural retreat just under a mile from San Quirico d'Orcia, a picturesque town in the heart of Tuscany. The property has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation features a spacious garden and a swimming pool, perfect for relaxing and enjoying the peaceful surroundings. Guests can also take advantage of a restaurant, free Wi-Fi, and private parking on-site.

Best pet friendly Pienza holiday rentals

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

Villa Le Fontanelle By Fantasia Villas - Pienza
No reviews

Villa Le Fontanelle By Fantasia Villas

house, Pienza
This seven-bedroom house is located in Pienza, just 2.1 kilometres from the Art Studio di Adelina Quadri and within a 10 kilometre radius of other cultural attractions like the Palazzo Borgia and the Civic Museum.
The 700 square metre property boasts a private swimming pool, jacuzzi, tennis court and a fully equipped kitchen, comfortably accommodating up to 14 guests.
Agriturismo Selvoli - La Civetta - Pienza
10 30 reviews

Agriturismo Selvoli - La Civetta

gîte, Pienza
This charming one-bedroom cottage is situated in the beautiful Val d'Orcia, just 5 kilometres from both Pienza and Bagno Vignoni, two of the region's most popular destinations. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The cottage features a cosy living-dining area with a fireplace and a fully equipped kitchen, comfortably accommodating up to 3 guests. Guests can enjoy a private patio with a covered area, a barbecue, and a stunning panoramic swimming pool overlooking the Val d'Orcia and Monte Amiata during the summer months.
Timilia - Pienza
No reviews

Timilia

apartment, San Quirico d'Orcia
This newly constructed flat offers a peaceful yet strategic base for exploring the Val d'Orcia, conveniently situated for accessing the region's renowned landscapes.
This two-bedroom, two-bathroom flat accommodates up to four guests and features air conditioning, Wi-Fi, and private parking, making it ideal for a Tuscan countryside experience.
Tuscany Green Apartment - Pienza
10 8 reviews

Tuscany Green Apartment

apartment, San Quirico d'Orcia
Tuscany Green Suite is located in San Quirico d'Orcia, a 4.5 kilometre drive from Bagno Vignoni and 22.5 kilometres from Bagni San Filippo, placing it conveniently for exploring the region's thermal spas and within 46.5 kilometres of Siena. This 40 square metre, one-bedroom flat accommodates two guests and features a fully equipped kitchen, air conditioning, complimentary WiFi, and a terrace, with pets welcome.
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