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Pienza villas
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19 Villa rentals in Pienza

Top-Rated Holiday Homes with a Pool in Pienza, Italy

Find houses with a pool in Pienza, Italy for a private swim whenever you feel like it.

Podere Spedalone - Pienza
8.8 976 reviews

Podere Spedalone

farm, Pienza
Podere Spedalone is a charming farmhouse located in the Tuscan countryside, just 4.3 miles from Pienza and 12 miles from Montepulciano, offering a peaceful retreat amidst rolling hills. It has consistently received excellent ratings for location, cleanliness, and overall experience.
The farmhouse features comfortable and charming rooms with private bathrooms, a large garden to explore, and a refreshing outdoor pool. Guests can enjoy a daily buffet breakfast featuring delicious homemade treats, dine at the on-site restaurant serving authentic Tuscan cuisine, and relax in the peaceful surroundings.
50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Pienza
9.4 19 reviews

50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Montepulciano
Farm for up to 2 people with an excellent rating of 94% based on 19 reviews. You will be in Montepulciano.
Services and facilities: a tennis court, rooms suitable for events and a barbecue. Take a dip in the pool of this accommodation in Montepulciano!
Agriturismo Pascianella Appartamento Bel Tramonto - Pienza
10 4 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.
30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
9.4 21 reviews

30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Castiglione d'Orcia
Accommodation for 4 people with an excellent rating of 94% based on 21 reviews. This accommodation is located in Castiglione d'Orcia.
Facilities and services include air conditioning, a sauna and a kitchen. Take advantage of the Free Parking with this accommodation.

Superior Family Holiday Homes in Pienza, Italy

Give the family a spacious home base with private yards and room for everyone at family houses in Pienza, Italy.

170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests - Pienza
No reviews

170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests

house, Montepulciano
Villa Boschetto, situated in the Val d'Orcia vineyards near Montepulciano, offers a tranquil escape amongst olive groves.
This 170 square metre property boasts five en-suite bedrooms, sleeping up to twelve guests, a private pool (12m x 7m), and a fully equipped kitchen including a dishwasher, alongside BBQ and wood-fired oven facilities.
House ∙ 4 Bedrooms ∙ 7 Guests - Pienza
No reviews

House ∙ 4 Bedrooms ∙ 7 Guests

house, Pienza
This villa is situated in the Val d'Orcia, a UNESCO World Heritage site, 5 kilometres from Pienza and San Quirico d'Orcia, offering views of the Tuscan countryside and proximity to the Vitaleta Chapel.
This family-friendly property accommodates up to 7 guests in 4 bedrooms, featuring a private swimming pool, a 5000 m² garden with barbecue facilities, Wi-Fi, and private parking, with domestic help, babysitter or chef services available on request.
Villa "Podere Spagliarda" With Private Pool, Terrace & Wi-fi - Pienza
No reviews

Villa "Podere Spagliarda" With Private Pool, Terrace & Wi-fi

house, San Quirico d'Orcia
This four-bedroom, four-bathroom farmhouse, sleeping up to twelve guests, is situated in San Quirico d'Orcia, within 5km of Piazza delle Sorgenti, Pieve di Corsignano, and Tenuta Sanone, and 10km from the Artemisia Gallery and Enoteca Di Ghino.
The 140 square metre property boasts a swimming pool, garden, parking, and a fully equipped kitchen with fridge and dishwasher; barbecue facilities are also available for guests to enjoy.
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.

Frequently asked questions about villa rentals in Pienza

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

    You absolutely must visit the Duomo, a stunning example of Renaissance architecture. The panoramic views from the top of the hill are incredible, especially from the Piazza Pio II. For a taste of the local history, head to the Museo Diocesano, housed in a former monastery. And if you're looking for a day trip, the charming medieval town of Montepulciano is just a short drive away.
  • 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, where Pienza sits, is home to a variety of wildlife. You might spot red deer, wild boar, and even the occasional fox in the surrounding hills. The area is also known for its birdlife, with species like the kestrel and the hoopoe often seen soaring overhead.
  • 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) are the ideal times to visit Pienza. The weather is pleasant, the crowds are smaller, and the landscape is at its most vibrant. You can enjoy the outdoors without the scorching summer heat or the chilly winter temperatures.
  • 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 during the shoulder seasons, like spring or autumn, is generally easier. You'll have a wider selection and potentially better prices. However, if you're looking for a summer getaway, it's best to book well in advance, especially if you have a large group.
  • 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 is a popular hiking trail that runs through the Val d'Orcia, offering stunning views of the rolling hills and vineyards. The trail starts in the village of San Quirico d'Orcia and leads to Pienza. Another great option is the Sentiero della Via Francigena, which follows the ancient pilgrimage route through the region.
  • 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 in Pienza offers a great deal of privacy and independence. You can enjoy your own space, cook your own meals, and relax at your own pace. It's also a great option for families or groups of friends who want to spend quality time together.
  • 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! Siena, with its iconic Piazza del Campo, is a must-see, just a short drive away. The charming town of Montepulciano, known for its Vino Nobile, is also within easy reach. For a taste of Etruscan history, head to the archaeological site of Chiusi, about 30 km from Pienza.

Popular destinations

Best Pienza villas and holiday homes with parking

B&b Daria - Deb's Monticchiello - Pienza
10 606 reviews

B&b Daria - Deb's Monticchiello

B&B, Pienza
Deb's Monticchiello is a charming bed and breakfast located in the village of Monticchiello, just 15 kilometres from the renowned wine region of Montepulciano and 35 kilometres from Lake Trasimeno. This family-friendly property has received excellent ratings for its location, cleanliness, and overall user experience.
The bed and breakfast features a relaxing garden with a sun terrace, perfect for enjoying the Italian sunshine. Guests can also enjoy a continental breakfast at the on-site restaurant, which offers a taste of Italian flavours to start the day. The property also provides free Wi-Fi access throughout, as well as air-conditioned rooms with a TV and private bathrooms.
Agriturismo Il Casato Mag-il Giogo - Pienza
9.4 28 reviews

Agriturismo Il Casato Mag-il Giogo

farm, Pienza
Agriturismo il Casato Mag-il Giogo, near Pienza, enjoys a convenient location 8.7km from Bagno Vignoni's thermal springs and 43km from Monte Amiata, offering easy access to Tuscany's renowned hilltop towns.
This 135 square metre property features two bedrooms and two bathrooms, accommodating up to 16 guests, and includes a fully equipped kitchen, terrace, garden, free Wi-Fi, free parking, and table tennis.
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.
Il Tramonto Di Pienza - Pienza
9.0 4 reviews

Il Tramonto Di Pienza

house, Pienza
Pienza Apartment with garden is situated in Pienza, Tuscany, offering easy access to local attractions in the historic town centre.
This 60 square metre house sleeps nine guests and features a fully equipped kitchen with dishwasher, air conditioning, a private garden with outdoor dining, free parking, and Wi-Fi.

Best Pienza villas and holiday homes with a garden

Podere Bagnolo 8 Emma Villas - Pienza
No reviews

Podere Bagnolo 8 Emma Villas

house, Pienza
PODERE BAGNOLO 8 is located in Pienza, 48 kilometres from Mount Amiata, 18 kilometres from Parco dei Mulini, and 29 kilometres from Bagni San Filippo, with Perugia San Francesco d'Assisi Airport 80 kilometres away.
This spacious villa offers 157 square metres of living space with four bedrooms and four bathrooms, accommodating up to 14 guests, and features a seasonal outdoor swimming pool, hot tub, garden, air conditioning, and a fully equipped kitchen, though it is not suitable for bachelor(ette) parties.
Agriturismo Podere San Gregorio - Pienza
9.2 219 reviews

Agriturismo Podere San Gregorio

farm, Pienza
Agriturismo Podere San Gregorio is a restored farmhouse located just a short walk from the centre of Pienza, a charming medieval town in the heart of Tuscany. It is also within easy reach of other popular destinations like Montepulciano and Siena. The property has received excellent ratings for its location, cleanliness and overall experience.
The farmhouse offers comfortable accommodation with a private garden and free BBQ facilities. Guests can enjoy a delicious breakfast basket delivered to their room each morning and have the option of purchasing locally produced olive oil and wine.
Castelmuzio By Posarellivillas - Pienza
9.9 151 reviews

Castelmuzio By Posarellivillas

house, Trequanda
This PosarelliVillas property in Castelmuzio, near Trequanda, is conveniently located a 21km drive from Bagno Vignoni, 26km from Montepulciano Terme, and 35km from Bagni San Filippo.
The 85 square metre villa offers two bedrooms, two bathrooms, a private pool, terrace, garden, parking, and a fully equipped kitchen including a dishwasher, accommodating up to four guests and featuring amenities such as a washing machine and barbecue.
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.

Enjoy Top-Rated Luxury Houses in Pienza, Italy

Treat yourself to high-end design, custom furniture, and premium finishes at luxury small-city houses in Pienza, Italy.

Agriturismo Cretaiole - Pienza
9.8 48 reviews

Agriturismo Cretaiole

farm, Pienza
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