Villas and Holiday homes in Pienza

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Pienza villas
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19 Villa rentals in Pienza

Best Pienza villas and holiday homes with a pool

Among the 19 accommodations in Pienza, here are the 4 best villas and holiday homes with a pool

Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking - Pienza
9.7 68 reviews

Villa Fè -Choose Panoramic View, Jacuzzi, Private Parking

house, Montepulciano
Villa Fè is situated in the Tuscan countryside, just 7.4 kilometres from the charming town of Montepulciano and 4.6 kilometres from the thermal baths of Montepulciano Terme. This property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The villa is a spacious three-bedroom property, covering 90 square metres. Enjoy a range of amenities including a private pool, hot tub, fitness centre, and a fully equipped kitchen, perfect for relaxing and exploring the beautiful Tuscan region.
Passiontoscane - Pienza
10 1 review

Passiontoscane

house, Montalcino
PassionToscane, a 120-square-metre house in San Giovanni d'Asso, is situated 24km from Bagno Vignoni and 45km from Siena's Piazza del Campo, offering easy access to Tuscan attractions.
This two-bedroom property sleeps seven, boasting a private garden with a swimming pool, a fully equipped kitchen including a dishwasher, free Wi-Fi, and private parking; a patio with barbecue facilities is available during warmer months.
La Villa Bella Vista - Pienza
9.6 8 reviews

La Villa Bella Vista

house, Trequanda
Villa Bella Vista, located in Castelmuzio, offers a luxurious self-catering property a short drive (22.5km and 24km respectively) from Bagno Vignoni and Montepulciano Terme, providing easy access to thermal baths and cultural attractions.
This 140 square metre Tuscan villa boasts two bedrooms, two bathrooms, and a spacious layout accommodating up to nine guests, complete with a private pool, Jacuzzi, free Wi-Fi, and parking.
50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Pienza
9.4 19 reviews

50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Montepulciano
Farm listing for 2 guests with an excellent rating of 94% based on 19 reviews. This accommodation is located in Montepulciano.
Facilities and services include a restaurant, rooms suitable for events and a washing machine. Take advantage of the air conditioning in this accommodation in Montepulciano.

Best family friendly Pienza villas and holiday home

Among the 19 accommodations in Pienza, here are the 4 best family friendly villas and holiday homes

Agriturismo La Casa Nuova - Pienza
9.7 122 reviews

Agriturismo La Casa Nuova

farm, Trequanda
Agriturismo La Casa Nuova is a charming farmhouse located just 5 kilometres outside the town centre of Trequanda, offering a peaceful escape from the bustle of the town. It has received excellent ratings for its location, cleanliness, and overall experience.
The property features a range of amenities, including a swimming pool, garden, and terrace, perfect for enjoying the Tuscan sunshine. Guests can also take advantage of the free parking, laundry services, and multilingual staff.
Agriturismo Il Casalino - Pienza
9.6 715 reviews

Agriturismo Il Casalino

farm, Pienza
Agriturismo Il Casalino is a 19th-century farmhouse located in Pienza, a UNESCO World Heritage site, just 39 kilometres from Siena and 47 kilometres from Arezzo, offering stunning views of the Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers independent apartments with a rustic interior design, each with its own entrance. Guests can enjoy a range of amenities including a terrace with panoramic views, a garden, free parking, WiFi, and the option to rent bikes to explore the surrounding area.
Casa Con Giardino  Villa Emma - Pienza
9.9 28 reviews

Casa Con Giardino Villa Emma

house, Pienza
This Pienza apartment is conveniently located near the town centre, offering easy access to shops and restaurants, and is within easy walking distance of Pienza's historic Piazza Pio II.
The self-catering property features a fully equipped kitchen, a double bedroom, a living room with a sofa bed sleeping four, a private garden, free Wi-Fi, and parking; Tuscan cooking classes and wine tasting are optionally available.
Didi House - Pienza
9.5 19 reviews

Didi House

house, Montepulciano
Didi House is situated in Montepulciano, a 7.7 kilometre drive from the Montepulciano Terme thermal baths and within easy reach of other attractions like Bagno Vignoni (22.5 kilometres) and Bagni San Filippo (30.5 kilometres). It has received excellent ratings for cleanliness, location and user experience.
This 2-bedroom property spans 126 square metres and accommodates up to four guests. Amenities include a fully equipped kitchen, a private terrace and garden, free parking, air conditioning, internet access, and a barbecue.

Frequently asked questions about villa rentals in Pienza

  • What are the must-see attractions in and around Pienza?

    You simply must visit the Duomo, with its stunning Renaissance architecture, and the Palazzo Piccolomini, offering breathtaking views of the Val d'Orcia. For a unique experience, explore the underground tunnels of the town's historic water system. Just outside Pienza, the rolling hills of the Val d'Orcia offer picturesque landscapes and charming medieval villages like Monticchiello and San Quirico d'Orcia.
  • What are the best villa rentals in Pienza?

    Among the villa rentals in Pienza, Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Pienza?

    The Val d'Orcia is home to a variety of wildlife, including red deer, wild boar, and a variety of bird species. If you're lucky, you might even spot a golden eagle soaring overhead. Keep your eyes peeled for hares and foxes as well, especially in the early morning or late evening.
  • What are the best villa rentals with a pool in Pienza?

    Agriturismo Il Macchione, Poggio Ai Gelsi and Agriturismo La Collina are the best villa rentals with a pool in Pienza.

  • What is the best time to visit Pienza?

    Spring (April-May) and autumn (September-October) offer the most pleasant weather for exploring the region. The landscape is vibrant and green in spring, while autumn brings warm days and stunning colours. Summer can be hot and crowded, but the warm weather is ideal for swimming in the nearby Lago Trasimeno.
  • What are the best villa rentals with a jacuzzi in Pienza?

    The best villa rentals with a jacuzzi in Pienza are Agriturismo Il Macchione, Poggio Ai Gelsi and Villa I Cipressini Piscina Riscaldata Spa Toscana.

  • When is it easiest to book a villa rental in Pienza?

    Booking a villa rental in Pienza is easiest during the shoulder seasons (April-May and September-October). You'll find better prices and fewer crowds compared to the peak season (June-August). Booking well in advance is always recommended, especially for popular periods like Easter and Christmas.
  • What are the best villa rentals for families and kids in Pienza?

    The best villa rentals for families and kids in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati.

  • What are the top hiking trails near Pienza?

    The Sentiero del Cassia, a scenic trail that follows an ancient Roman road through the Val d'Orcia, is a popular choice. The Via Francigena, a historic pilgrimage route, also passes through the area, offering breathtaking views and charming villages along the way. For a shorter hike, explore the trails around the Sanctuary of Sant'Anna in Camprena, just outside Pienza.
  • What are the best pet friendly villa rentals in Pienza?

    The best pet friendly villa rentals in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Poggio Ai Gelsi.

  • What are the advantages of renting a house or a villa in Pienza

    Renting a villa offers a more private and spacious experience compared to a hotel. You'll have your own kitchen, living space, and outdoor areas, giving you the flexibility to create your own schedule and enjoy meals at your own pace. Many villas also come with amenities like a swimming pool and a garden, perfect for relaxing and enjoying the Tuscan countryside.
  • What are the best villa rentals with parking in Pienza?

    Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the best villa rentals with parking in Pienza.

  • Are there popular destinations near Pienza?

    Absolutely! The charming hilltop town of Montepulciano, known for its excellent wine, is just a short drive away. Siena, with its iconic Piazza del Campo, is another popular destination, offering a glimpse into the rich history and culture of Tuscany. For a day trip, consider visiting the beautiful city of Perugia, perched on a hill overlooking the Umbrian countryside.

Popular destinations

Best Pienza villas and holiday homes with parking

Agriturismo Sant'agostino - Pienza
8.6 70 reviews

Agriturismo Sant'agostino

farm, Montalcino
Agriturismo Sant'Agostino, a renovated farmhouse near San Giovanni d'Asso, is situated approximately 42km from Siena's Piazza del Campo and 22km from Bagno Vignoni, offering easy access to the Val d'Orcia and its renowned wineries.
This self-catering property features a swimming pool, a terrace, a garden, free Wi-Fi, and private parking; selected rooms include kitchens with dishwashers, and all rooms are air-conditioned.
Villa Agriturismo Il Pratone - Pienza
8.9 21 reviews

Villa Agriturismo Il Pratone

house, Castiglione d'Orcia
Villa Agriturismo Il Pratone is located just 5km from Bagno Vignoni and 32km from Mount Amiata, offering easy access to the picturesque Tuscan countryside. The property has received excellent ratings for cleanliness and location, ensuring a comfortable and enjoyable stay.
The farmhouse offers two bedrooms, a living room, satellite TV, an equipped kitchen, and two bathrooms. Guests can enjoy a private patio with mountain views, a private pool, a fireplace, barbecue facilities, free Wi-Fi, and private parking.
90 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

90 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Torrita di Siena
This secluded rural property, offering a tranquil escape, is situated in a panoramic location near Montefollonico (1.3 km) and Montepulciano (7 km), boasting spectacular views of the Montepulciano valley, San Biagio temple, Monte Amiata, and the Val d'Orcia hills.
This holiday home, spanning 90 square meters and accommodating up to six guests, features two independent stone houses, including the restored 17th-century Casa MULINELLO with a living room, two fireplaces, and two panoramic terraces, along with a kitchen equipped with a fridge and dishwasher, and is pet and family friendly with internet and parking.
Agriturismo Il Macchione - Pienza
9.3 571 reviews

Agriturismo Il Macchione

house, Pienza
This 18th-century farmhouse is located just 0.9 miles outside of Pienza, overlooking the stunning Val d'Orcia Natural Park, offering a secluded and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse features a spacious terrace with a swimming pool and hydromassage area, perfect for relaxing and enjoying the beautiful surroundings. Guests can also enjoy a range of amenities, including a fitness center, tennis court, and a children's playground, as well as a buffet breakfast and BBQ facilities.

Best Pienza villas and holiday homes with a garden

La Casa Di Vignoni Alto - Pienza
8.7 65 reviews

La Casa Di Vignoni Alto

house, San Quirico d'Orcia
La Casa di Vignoni Alto is a holiday home located in the village of Bagno Vignoni, 1.9 kilometres from the famous thermal baths and a short drive from other attractions such as Bagni San Filippo (19 kilometres) and Montepulciano Terme (29 kilometres).
The 250 square metre property features two bedrooms, two bathrooms, and can accommodate up to nine guests, and offers amenities such as a fully equipped kitchen, a garden, a tennis court, and free Wi-Fi.
200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
No reviews

200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

house, Torrita di Siena
Villa Tiberini - Casale il Pecino, located within the Tiberini Estate in Montepulciano, offers a rural retreat in Torrita di Siena with mountain and city views, situated a short distance from the historic centre of Montepulciano. This 200 square meter villa accommodates up to eight guests across four bedrooms and four bathrooms, boasting a private outdoor pool and garden, barbecue facilities, and access to shared amenities at Villa Tiberini Wine Relais including a communal kitchen and playground, with opportunities for wine tastings and local produce sampling.
Casa La Vittoria - Pienza
10 106 reviews

Casa La Vittoria

house, Pienza
This Pienza apartment rental, located in the central Monticchiello, offers stunning Val d'Orcia and Monte Amiata views, and is a short walk from the owner's Daria restaurant.
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen, free Wi-Fi, a furnished terrace, and provides guests with 24/7 access alongside opportunities for local experiences such as cooking classes and wine tastings.
La Maison De Elena Tuscany - Pienza
9.2 34 reviews

La Maison De Elena Tuscany

house, Montepulciano
La Maison de Elena Tuscany is a villa situated 2.9 miles from Montepulciano Terme and 12 miles from Bagno Vignoni, offering a peaceful retreat in the Tuscan countryside. The property boasts excellent user and cleanliness ratings, with a good location rating.
This one-bedroom villa provides 100 square metres of space, comfortably accommodating up to four guests. The villa features a fully equipped kitchen, a private hot tub, a terrace with garden views, and access to a spa, barbecue facilities, and a peaceful garden.
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