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

La Romita Ospitalità Rurale Familiare - Pienza
8.9 128 reviews

La Romita Ospitalità Rurale Familiare

farm, Montalcino
La Romita Ospitalità Rurale Familiare is situated in Montisi, a charming village just a 30-minute drive from Montepulciano, offering a peaceful escape in the Tuscan countryside. The farm has received very good user ratings and excellent ratings for its location and cleanliness.
The rural retreat offers a range of country-style rooms with tile or hardwood floors and wrought iron beds. Guests can enjoy a delicious local Tuscan breakfast, relax in the garden with its outdoor seating area, and take advantage of amenities such as laundry facilities and a restaurant serving regional specialties.
Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi - Pienza
No reviews

Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi

house, Trequanda
This detached villa is located in Trequanda, a Tuscan town with convenient access to Siena (60 kilometres), Florence (100 kilometres), Pienza (20 kilometres), and Montepulciano (15 kilometres).
This 156 square meter, two-storey holiday home offers three bedrooms, three bathrooms, and accommodates up to six guests, featuring Wi-Fi, air conditioning, a dishwasher, a private balcony, and access to a shared swimming pool.
Podere Le Mulina - Pienza
8.5 85 reviews

Podere Le Mulina

farm, Castiglione d'Orcia
Podere le Mulina is a farm stay located in Castiglione d'Orcia, just 5.5 kilometres from Bagno Vignoni and 35 kilometres from Mount Amiata, offering a peaceful escape in the Tuscan countryside. It has received very good ratings for its cleanliness and overall user experience, with a good location rating.
The farm stay features a fully equipped kitchen with a fridge, oven, and stovetop, allowing guests to prepare their own meals. Guests can enjoy the outdoor amenities, including a swimming pool, a garden, and a picnic area, perfect for relaxing and enjoying the Tuscan sunshine.
Agriturismo Bonello - Pienza
9.4 519 reviews

Agriturismo Bonello

farm, Pienza
Agriturismo Bonello is a historic farmhouse located just outside Pienza, a charming medieval town, with stunning views of the Val D’Orcia nature reserve, a UNESCO World Heritage Site, and a short drive from Siena. The property has excellent user, location and cleanliness ratings.
The farmhouse offers a range of self-catering apartments, each with a fully equipped kitchen. Guests can enjoy a refreshing dip in the outdoor pool, relax in the Jacuzzi, or unwind in the sauna and spa.

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

156 M² Chalet ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

156 M² Chalet ∙ 3 Bedrooms ∙ 6 Guests

chalet, Torrita di Siena
This detached villa in Torrita di Siena is located in the Cignella area, offering panoramic views of the Tuscan landscape.
This spacious 156 square meter villa accommodates up to six guests across three bedrooms and three bathrooms, featuring an open-plan living area, a fully equipped kitchen with a dishwasher and washing machine, air conditioning, a swimming pool, a terrace for al fresco dining, and parking.
Chalet Cigno Cignella Resort - Pienza
No reviews

Chalet Cigno Cignella Resort

chalet, Trequanda
This charming chalet is situated in Trequanda, just 18km from Montepulciano Terme and 26km from Bagno Vignoni, offering a peaceful retreat in the Tuscan countryside. The property provides a tranquil setting for exploring the region's rich history and culture.
The chalet spans 80 square metres and comfortably accommodates up to 5 guests in its two bedrooms. Enjoy a range of amenities including a shared swimming pool, a terrace with mountain views, a garden, and free Wi-Fi.
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.
Wp Relais Villa Vignalunga - Pienza
10 2 reviews

Wp Relais Villa Vignalunga

house, Castiglione d'Orcia
Wp Relais Villa Vignalunga, near Bagno Vignoni (4.2km) in Castiglione d’Orcia, offers easy access to other Tuscan towns such as Bagni San Filippo (19km) and Montepulciano Terme (26km).
This 400 square metre villa boasts three bedrooms, four bathrooms each with a hot tub, a swimming pool, Jacuzzi, spa, and parking; sleeping up to 15 guests and featuring a well-equipped kitchen and stunning garden views.

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 Palazzo Conti A - Pienza
9.3 140 reviews

Agriturismo Palazzo Conti A

house, San Quirico d'Orcia
Agriturismo Palazzo Conti A is located just outside Pienza, a short drive from Montalcino, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartments are classically decorated and feature flat-screen TVs, seating areas, and fully equipped kitchenettes. Guests can enjoy a range of amenities including a swimming pool, a natural pool, a garden with BBQ facilities, a spa, a restaurant, a bar, and room service.
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.
Cozy Home In San Quirico D'orcia - Pienza
8.0 5 reviews

Cozy Home In San Quirico D'orcia

house, San Quirico d'Orcia
This holiday home in San Quirico d'Orcia is situated 5.3km from Bagno Vignoni, a thermal spa town, and within a 40-50km radius of Montepulciano Terme, Bagni San Filippo, and Siena.
The 70 square metre property boasts one bedroom, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen with dishwasher and fridge, free Wi-Fi, private parking, and a garden.
Villa  Piscina , Giardino E Relax Toscano - Pienza
10 7 reviews

Villa Piscina , Giardino E Relax Toscano

house, Montalcino
Villa Santa Caterina, near Montisi, offers a convenient base for exploring Montalcino, Pienza (a short drive away), and Montepulciano, all within the Val d'Orcia.
This two-bedroom, two-bathroom property sleeps four, boasting a private pool, well-maintained garden, fully equipped kitchen, and free parking; ideal for wine tasting and hiking in the stunning Tuscan countryside.

Best Pienza villas and holiday homes with a garden

Cosy Apartment With A/c, Wifi, Pool, Tv, Terrace And Pets Allowed, Close To Montepulciano - Pienza
No reviews

Cosy Apartment With A/c, Wifi, Pool, Tv, Terrace And Pets Allowed, Close To Montepulciano

farm, Trequanda
This farm stay is located in the Orcia Valley, 10 kilometres from Torrita di Siena and 16 kilometres from Montepulciano, offering scenic views and proximity to towns such as Montalcino and Siena.
This 70 square metre apartment sleeps up to three guests, featuring two bedrooms, one bathroom, a fully-equipped kitchen with a fridge, microwave and dishwasher, air conditioning, WiFi, and access to a shared outdoor swimming pool, with cooking lessons and custom tours also available.
Agriturismo Riposati - Pienza
9.6 255 reviews

Agriturismo Riposati

house, Pienza
This house is located near Monticchiello, a charming village just 2 kilometres away, and a short 20-minute drive from the famous town of Montepulciano. It has received excellent ratings for location, cleanliness and user experience.
The house has one bathroom and features a fully equipped kitchen, a garden and free Wi-Fi. Guests can enjoy stunning views of the Val d'Orcia hills and relax in the tranquil garden setting.
Le Maribelle - Pienza
8.2 77 reviews

Le Maribelle

house, Pienza
Le Maribelle is a charming house located in Monticchiello, a picturesque village just a short drive from Pienza and 27 miles from Mount Amiata. Guests have consistently rated the house as very good for cleanliness and location, with excellent overall feedback.
This two-bedroom house features a fully equipped kitchen, a terrace with garden views, and air conditioning. Guests can enjoy the peaceful village atmosphere, explore the surrounding area by bicycle, and make use of the on-site restaurant, mini-market, and ATM.
Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza
Farm for up to 3 people. You will be located in Pienza.
Facilities and services: a dish washer, a barbecue and a kitchen. Enjoy free parking with this accommodation in Pienza!
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