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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.

Agriturismo San Marcello - Pienza
9.4 358 reviews

Agriturismo San Marcello

farm, Castiglione d'Orcia
Agriturismo San Marcello is located in Castiglione d'Orcia, a short drive from the thermal baths of Bagno Vignoni and Bagni San Filippo, offering a peaceful escape in the Tuscan countryside. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The farm offers spacious accommodation units, some with fully equipped kitchens and private bathrooms. Guests can enjoy a continental breakfast, relax on the sun terrace, or explore the surrounding area with skiing and cycling opportunities.
Camera Il Giardino - Pienza
10 1 review

Camera Il Giardino

gîte, Pienza
This Val d'Orcia farmhouse, a short drive from Pienza, offers a taste of authentic Tuscan life in a UNESCO World Heritage site.
The self-catering property sleeps three, boasting a bedroom, bathroom, garden access, a swimming pool, and includes complimentary breakfast and local wine tasting.
Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.5 64 reviews

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Pienza
Farm for up to 5 people with an excellent rating of 95% based on 64 reviews. You will be in Pienza.
Facilities and services: a fridge, a restaurant and a kitchen. This accommodation in Pienza is ideal for families.
Le Sorbelle D'orcia - Pienza
9.5 144 reviews

Le Sorbelle D'orcia

farm, Pienza
Agriturismo Le Sorbelle d'Orcia, near Pienza in Tuscany, is conveniently located 19 kilometres from Montepulciano Terme, 21 kilometres from Bagni San Filippo, and 4.3 kilometres from Bagno Vignoni, offering easy access to these popular towns.
This one-bedroom, one-bathroom rural retreat sleeps three guests and boasts a swimming pool, free private parking, and a varied breakfast; bachelor/hen parties are not permitted.

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.

Villa Aquila-cignella Resort Acommodation  Tuscany - Pienza
10 1 review

Villa Aquila-cignella Resort Acommodation Tuscany

house, Torrita di Siena
Villa Aquila, a luxurious apartment within the Cignella Resort in Torrita di Siena, offers private garden access and is conveniently located within walking distance of Torrita di Siena's main square.
This three-bedroom, three-bathroom dwelling sleeps six guests and boasts a double-height living room with exposed beams, a well-equipped kitchenette, and en-suite bedrooms; the resort offers additional amenities.
Agriturismo Torrenieri Da Alessandro - Pienza
9.1 77 reviews

Agriturismo Torrenieri Da Alessandro

farm, Trequanda
Agriturismo Torrenieri da Alessandro is situated in the Val d'Orcia, a short drive from the picturesque towns of Pienza, San Quirico d’Orcia, and Montepulciano. The property enjoys excellent ratings for its location, cleanliness, and overall guest experience.
The self-catering apartments offer a traditional Tuscan ambiance, with wood-beamed ceilings and terracotta floors. Guests can enjoy on-site olive oil production, complimentary bikes for exploring the area, a garden with BBQ facilities, and breakfast essentials provided in their accommodation.
Agriturismo Marinello - Pienza
9.4 595 reviews

Agriturismo Marinello

farm, Pienza
Agriturismo Marinello is located in the Val d’Orcia, a UNESCO World Heritage Site, just 4km from the centre of Pienza and a 32km drive from Montalcino. The farm has received excellent ratings for location, cleanliness and overall experience.
The farm offers both rooms and apartments, all with traditional Tuscan features, like wood-beamed ceilings and wrought-iron beds. Guests can enjoy a private garden, a swimming pool open from May to September, and a fully equipped kitchen.
Villa In Totona With 6 Bedrooms Sleeps 12 - Pienza
No reviews

Villa In Totona With 6 Bedrooms Sleeps 12

house, Montepulciano
This luxurious six-bedroom villa in Montepulciano is situated a short 2.4km walk from the Val di Chiana and Triacca Winery, and within 3.2km of San Biagio and Torre del Pulcinella.
The 550 square metre property boasts a private pool, Jacuzzi, sauna, spa, and fitness centre, accommodating up to 12 guests and featuring a fully equipped kitchen and six bathrooms.

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

Le Corolle - Pienza
9.2 142 reviews

Le Corolle

house, Montepulciano
Le Corolle is a holiday home located just 2 kilometres outside of Montepulciano, offering a peaceful retreat close to the town's attractions. The property has consistently received excellent ratings for location, cleanliness and overall user experience.
The self-catering accommodation features a well-equipped kitchenette, a private bathroom, a terrace and a garden. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace, cook up a meal on the barbecue, or make use of the free private parking.
Agriturismo Bagnolo - Pienza
9.0 234 reviews

Agriturismo Bagnolo

farm, Pienza
Agriturismo Bagnolo is a farm stay situated in the Tuscan countryside, just 4km from the historic town of Pienza, and within easy reach of Montepulciano and Chianciano Terme. This highly-rated property boasts excellent user, location, and cleanliness ratings.
The farm offers a choice of rooms and apartments, accommodating up to two guests. Enjoy a range of amenities including a jacuzzi, terrace, garden, and parking, as well as the opportunity to participate in the production of oil and cheese, and witness the farm's animals firsthand.
Agriturismo I Capraccioni Monticchiello - Pienza - Pienza
9.3 180 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 Costanza - Pienza
9.5 45 reviews

Casa Costanza

house, Castiglione d'Orcia
Casa Costanza is located in Castiglione d'Orcia, a short drive from the renowned thermal baths of Bagno Vignoni and the picturesque village of Bagni San Filippo. The property has excellent user, location and cleanliness ratings.
The two-bedroom, two-bathroom property spans 68 square metres. Guests can enjoy stunning views, a shared lounge, an outdoor fireplace, a fully equipped kitchen, a flat-screen TV, complimentary Wi-Fi, bathrobes, towels and bed linen.

Best Pienza villas and holiday homes with a garden

La Tresa Country Living - Pienza
9.5 22 reviews

La Tresa Country Living

farm, Montepulciano
La Tresa Country Living is a farm stay located in Montepulciano, offering garden views and convenient access to local attractions.
This pet-friendly, family-friendly accommodation features one bedroom and one bathroom, with complimentary WiFi, private parking, a garden, a terrace, and an outdoor picnic area.
Casa Valerie - Pienza
8.8 4 reviews

Casa Valerie

house, Trequanda
Casa Valerie is situated in Castelmuzio, a charming village just 14 miles from Bagno Vignoni and 31 miles from Piazza Grande, offering easy access to the region's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom villa, spanning 150 square metres, comfortably accommodates up to four guests. The property features a private pool with mountain views, a spa bath, a fully equipped kitchen, an outdoor fireplace, and a peaceful garden, providing a relaxing and enjoyable stay.
Authentic Tuscan Villa With Infinity Pool & Stunning Views Of Val D'orcia - Pienza
10 6 reviews

Authentic Tuscan Villa With Infinity Pool & Stunning Views Of Val D'orcia

house, Torrita di Siena
This luxurious five-bedroom villa near Torrita di Siena enjoys a secluded rural setting in the Val di Chiana, within 10km of the Triacca Winery, Pienza's historic centre, and other local attractions.
Sleeping up to ten guests, this self-catering property boasts a private pool, jacuzzi, fitness centre, and fully equipped kitchen including a dishwasher, alongside five bathrooms, a terrace, garden, and parking; barbecue facilities and a washing machine are also provided.
Elegant Ground Floor Villa Of 93 M2 Consisting Of A Large Living Room With Sofas And Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Double Bedroom W - Pienza
No reviews

Elegant Ground Floor Villa Of 93 M2 Consisting Of A Large Living Room With Sofas And Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Double Bedroom W

house, Trequanda
Cignella Villa Rosmarino, a self-catering villa in Trequanda, Tuscany, is situated a short walk from the Val di Chiana and within 15km of the Saints Peter and Andrew Church, the Monastery of Sant'Anna in Camprena, Triacca Winery, and Enoteca Di Ghino.
This 93 square metre property sleeps four guests in two bedrooms and two bathrooms, offering a swimming pool, terrace, garden, parking, Wi-Fi, air conditioning, and a fireplace.

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.

Pienza By Posarellivillas - Pienza
9.6 244 reviews

Pienza By Posarellivillas

house, Pienza
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