Vacation Rentals in Pienza

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Pienza holiday rentals
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114 Holiday rentals and Airbnb in Pienza

Discover Exceptional Family Holiday Rentals in Pienza, Italy

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Pienza, Italy.

Villa Fonte All'oppio Con Area Piscina Recintata - Pienza
8.6 41 reviews

Villa Fonte All'oppio Con Area Piscina Recintata

house, Pienza
Villa Fonte all'Oppio is situated in the Tuscan countryside, just a short drive from the charming town of Pienza, a UNESCO World Heritage Site, and a little further from Montepulciano. The property has received very good ratings for cleanliness and user experience, and its location is considered excellent.
The villa offers spacious apartments with fireplaces, equipped kitchens, and private bathrooms. Guests can enjoy a refreshing dip in the private pool, relax in the lush garden, and prepare delicious meals using the provided BBQ facilities.
Agriturismo Podere La Paolina - Residenza Di Charme - Pienza
9.1 77 reviews

Agriturismo Podere La Paolina - Residenza Di Charme

farm, Torrita di Siena
Podere La Paolina is a farm stay situated in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering easy access to the Valdichiana and the beautiful Tuscan countryside. The property has received excellent ratings for cleanliness and location, making it a popular choice for travellers seeking a relaxing escape.
The accommodation offers a choice of rooms and self-catering apartments, all with private entrances and soundproofing for a peaceful stay. Guests can enjoy stunning garden views, a swimming pool, and a restaurant serving delicious Italian cuisine, as well as take advantage of the on-site yoga sessions, bicycle rental, and convenient amenities like free Wi-Fi and parking.
Apartment With Balcony In Historic House + Pool - Pienza
9.2 5 reviews

Apartment With Balcony In Historic House + Pool

apartment, Montalcino
Il Quartiere apartment in Montisi, a village near Pienza and Montalcino, offers a tranquil setting in the Tuscan countryside, conveniently located for exploring these towns and the wider region.
This one-bedroom, one-bathroom flat sleeps three, features a furnished balcony with valley views, a swimming pool, garden, parking, and offers access to cooking classes, wine tastings, and other activities.
Al Piccolo Ulivo, A Casa Di Mimo&sè - Pienza
9.5 25 reviews

Al Piccolo Ulivo, A Casa Di Mimo&sè

house, Castiglione d'Orcia
Al Piccolo Ulivo is located in Castiglione d'Orcia, just a short drive from the famous thermal baths of Bagno Vignoni and Mount Amiata, offering a peaceful retreat amidst the Tuscan countryside. This property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The villa provides comfortable accommodation for up to four guests in two bedrooms, spanning 106 square metres. Enjoy a well-equipped kitchen, modern amenities, and a shared lounge, along with a private garden offering stunning views and access to outdoor activities like skiing, cycling, and hiking in the surrounding area.

Best Pienza holiday rentals with parking

Terre Di Nano - Pienza
10 19 reviews

Terre Di Nano

farm, Pienza
Terre di Nano farm, in Val d'Orcia, is situated approximately 1.6km from Monticchiello, offering stunning views of Montepulciano and Pienza.
This one-bedroom, one-bathroom self-catering apartment in a 19th-century building features terracotta floors, exposed beams, a fully equipped kitchen, fireplace, swimming pool, and on-site olive oil and Chianti Terre di Nano wine tasting and tours.
Appartamento Olivo - Cignella Resort - Pienza
10 2 reviews

Appartamento Olivo - Cignella Resort

house, Trequanda
This spacious apartment in Trequanda is conveniently located just 53 miles from Perugia San Francesco d'Assisi Airport, offering a tranquil escape from the city. It has consistently received excellent ratings for cleanliness, location, and overall experience.
The apartment spans 118 square metres and features three bedrooms and three bathrooms, making it ideal for families or groups. Guests can enjoy a range of amenities including a private terrace, swimming pool, free Wi-Fi, and private parking.
Agriturismo I Capraccioni Monticchiello - Pienza - Pienza
9.3 182 reviews

Agriturismo I Capraccioni Monticchiello - Pienza

gîte, Pienza
This self-catering apartment, situated in the Val d'Orcia countryside, is 4km from Montepulciano and 2.5km from Monticchiello, offering easy access to these historic Tuscan towns.
The 80 sq m ground-floor property sleeps two, features a private garden with children's play area and barbecue, and includes a kitchen, bathroom, and on-site parking.
Casa Ilda Ac, Wifi Private Parking - Pienza
9.6 7 reviews

Casa Ilda Ac, Wifi Private Parking

house, Torrita di Siena
Casa Ilda, near Torrita di Siena, enjoys a convenient location approximately 16km from Montepulciano Terme, 32km from Bagno Vignoni, and 43km from Piazza Grande.
This 125 square metre property offers three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, air conditioning, free Wi-Fi, private parking with an EV charging station, and a terrace/garden.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town, but you also have a lot to see in the surrounding area. The Duomo di Pienza is a must-see, and the Palazzo Piccolomini is a great place to learn about the history of the town. For a day trip, visit the nearby town of Montepulciano, known for its Vino Nobile wine. If you're interested in art, the Museo Diocesano in Pienza is worth a visit.
  • 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?

    Pienza is perfect for exploring on foot. The historic centre is small and easily walkable, and there are plenty of charming alleyways to discover. For a longer walk, try the Sentiero della Val d'Orcia, which offers stunning views of the Tuscan countryside. If you prefer cycling, the Val d'Orcia is also great for a leisurely bike ride, with gentle hills and picturesque landscapes.
  • 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 base for exploring the Val d'Orcia, a UNESCO World Heritage Site. You can go hiking or mountain biking in the surrounding hills, or enjoy a picnic in one of the many vineyards. There are also opportunities for horseback riding and hot air ballooning in the area.
  • 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. For a day trip, visit the charming hilltop town of Montepulciano, just a short drive away. You can also easily reach the beautiful Lake Trasimeno, a popular destination for swimming and watersports.
  • 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 garden or terrace, and some even have a swimming pool. It's always a good idea to check the listing for specific details about the amenities offered.
  • 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 time of year is best to rent a vacation rental Pienza?

    The best time to visit Pienza is in 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. However, if you're looking for a quieter experience, winter can be a good time to visit.

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Discover Holiday Rentals with a Balcony in Pienza, Italy

Watch the local morning bustle with a fresh breeze at holiday rentals featuring an outdoor balcony in Pienza, Italy.

Casa Orcia - Pienza
9.4 5 reviews

Casa Orcia

apartment, San Quirico d'Orcia
This apartment in San Quirico d'Orcia is located 5.8 kilometres from Bagno Vignoni, 40 kilometres from Mount Amiata and 46 kilometres from Piazza del Campo.
This 83 square metre flat, suitable for up to 11 guests, offers two bedrooms, one bathroom, a fully equipped kitchen with dishwasher and oven, complimentary WiFi, air conditioning, a terrace, and private parking, with cycling opportunities in the Val d'Orcia.
La Casa Di Dina - Pienza
9.4 82 reviews

La Casa Di Dina

apartment, Trequanda
La Casa Di Dina is situated in the picturesque village of Castelmuzio, just 20km from the historic town of Montepulciano and 30km from Siena, in the beautiful Val d'Orcia region. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers seeking a peaceful and authentic Italian escape.
The apartment is spacious and comfortable, with 55 square metres of living space, including two bedrooms and one bathroom. It features a fully equipped kitchen, a cosy fireplace, a terrace with scenic views, and a swimming pool, offering a relaxing and enjoyable stay for families and couples alike.
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.
Farmhouse With Pool, Views - Pienza
10 9 reviews

Farmhouse With Pool, Views

farm, Castiglione d'Orcia
This Tuscan farmhouse rental in Castiglione d’Orcia is situated 2.6 km from Val d’Orcia and Terre di Siena, and within 10 km of Tenuta Sanone and Horti Leonini.
The self-catering property boasts a swimming pool, terrace, garden, parking, and barbecue facilities, and is pet-friendly with Wi-Fi.

Compare Pet-Friendly Holiday Rentals in Pienza, Italy

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Pienza, Italy.

Locanda Di Montisi Contrada Room Among The Hills Of Montalcino - Pienza
No reviews

Locanda Di Montisi Contrada Room Among The Hills Of Montalcino

apartment, Montalcino
This one-bedroom flat is located in the medieval village of Montisi, within the Crete Senesi region, offering a convenient base for exploring notable Tuscan towns such as Siena (approximately 50 kilometers away), Pienza (approximately 30 kilometers away), Montalcino (approximately 20 kilometers away), and Montepulciano (approximately 35 kilometers away).
This property accommodates two guests and features a traditional Tuscan style with exposed beams and terracotta floors, providing air conditioning, Wi-Fi, a TV, and self check-in, with nearby opportunities for spa visits, food and wine tours, and cycling.
A Casa Di Gabri By Interhome - Pienza
No reviews

A Casa Di Gabri By Interhome

apartment, Torrita di Siena
This detached house in the Montefollonico district, 10 kilometres from Montepulciano and 10 kilometres from Torrita di Siena centre, offers an isolated yet sunny position 500 metres from woodland and 200 metres from local shops and restaurants.
The 100 square metre, two-storey property sleeps five, features air conditioning in all bedrooms, a 500 square metre private garden with barbecue, and includes a washing machine, dishwasher, Wi-Fi, and parking for two cars, with baby equipment available on reservation.
130 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

130 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Torrita di Siena
Banditello Country House offers a tranquil, panoramic retreat near Torrita di Siena, situated 1.3 kilometres from Montefollonico and 7 kilometres from Montepulciano, boasting expansive views of the Montepulciano valley, San Biagio temple, Monte Amiata, and the Val d'Orcia hills. This restored stone property, spanning 120 square metres, accommodates up to six guests in three bedrooms with three bathrooms, featuring a kitchen with a fridge and dishwasher, a garden, parking, and an outdoor patio with sun loungers.
55 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.7 21 reviews

55 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Pienza
Farm listing for up to 5 guests with an excellent rating of 97% based on 21 reviews. Your accommodation will be based in Pienza.
Services and facilities: a solarium, a freeze and free parking. This is a family-friendly accommodation!
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