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Pienza holiday homes
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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 Podere Del Papa By Mmega - Pienza
No reviews

Villa Podere Del Papa By Mmega

house, Pienza
Villa Podere del Papa, situated in the Val d'Orcia within the Lucciola Bella Nature Reserve, is a few kilometres from Pienza, offering easy access to attractions such as the Art Studio di Adelina Quadri and Artemisia Gallery.
This 400 square metre property sleeps up to 18 guests in nine bedrooms and eight bathrooms across a main house and annex, boasting a private pool (open May 1st to October 30th), barbecue, and amenities including Wi-Fi and accessibility features.
Agriturismo La Poderina - Pienza
9.4 181 reviews

Agriturismo La Poderina

farm, Castiglione d'Orcia
Agriturismo La Poderina is a farm stay located just 0.6 miles from the spa town of Bagno Vignoni and a 20-minute drive from Montepulciano, set in the peaceful countryside of Castiglione d'Orcia. It has received excellent ratings for location, cleanliness, and user experience. The accommodation offers self-catering apartments with exposed-beam ceilings, creating a warm and inviting atmosphere. Guests can enjoy free Wi-Fi, on-site parking, BBQ facilities, and a swimming pool, as well as a terrace or balcony and a garden.
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 Basil, a self-catering villa in Trequanda, Tuscany, is situated within 15km of the Saints Peter and Andrew Church, the Monastery of Sant'Anna in Camprena, Triacca Winery and Enoteca Di Ghino, offering easy access to Val di Chiana's scenic beauty and notable wineries.
This 93 square metre property sleeps four guests in two bedrooms and two bathrooms, boasting a private swimming pool, garden, parking, and in-villa amenities including a fireplace, TV with DVD player, and washing machine.
Elegant And Spacious Two-storey Villa Of 156 M2 Composed Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Master Double Bedroom With Priv - Pienza
No reviews

Elegant And Spacious Two-storey Villa Of 156 M2 Composed Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Master Double Bedroom With Priv

house, Trequanda
Cignella Villa Salvia, a three-bedroom 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 Sant'Anna in Camprena Monastery, Triacca Winery, and Enoteca Di Ghino.
This self-catering property sleeps six, boasting three bathrooms, a fully equipped kitchen, a fireplace, a terrace, a garden, a swimming pool, parking, and internet access.

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

In Toscana Camere - Pienza
9.8 161 reviews

In Toscana Camere

house, Pienza
In Toscana Camere, you'll find a peaceful countryside retreat located just 10km from Pienza, a 24km drive from Montepulciano, and 48km from Montalcino. The property has received excellent ratings for cleanliness, location, and user experience.
The houses and apartments offer a blend of traditional Tuscan charm and modern amenities. Guests can enjoy a fully equipped kitchen, free Wi-Fi, air conditioning, and a garden, perfect for relaxing and enjoying the peaceful surroundings.
Suite Gioconda - Podere Casa Rossa In Pienza - Pienza
10 5 reviews

Suite Gioconda - Podere Casa Rossa In Pienza

apartment, Pienza
This family-friendly farmhouse, near Pienza's historic centre, offers a peaceful rural setting a short 0.6km walk from the Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile.
Sleeping four guests in two bedrooms and one bathroom, this self-catering property boasts a garden, air conditioning, Wi-Fi, a dishwasher, and parking, plus housekeeping is available on request.
Agriturismo Belagaggio - Pienza
9.5 521 reviews

Agriturismo Belagaggio

farm, Torrita di Siena
Agriturismo Belagaggio is located in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering stunning views of the surrounding countryside. The property has received excellent ratings for its location, cleanliness and overall experience.
This recently renovated farmhouse offers comfortable accommodation with a range of amenities including a swimming pool, jacuzzi, and terrace. Guests can enjoy a restaurant serving local cuisine, a spa, and a variety of activities such as cycling and hiking.
Podere Spedalone - Pienza
8.8 972 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.

Frequently asked questions about villa rentals in Pienza

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

    Pienza is a gem! You absolutely must visit the Duomo, a stunning example of Renaissance architecture. Take a stroll through the Piazza Pio II, the heart of the town, and enjoy the views from the Palazzo Piccolomini. If you're looking to explore the surrounding area, the Val d'Orcia is a must-see, with rolling hills and charming villages like Montepulciano and Montalcino.
  • 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 foxes. You might also spot birds of prey like buzzards and kestrels. Keep an eye out for the occasional hare or badger too.
  • 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 mild, the crowds are smaller, and the landscape is at its most vibrant. You can enjoy the fresh air and the beautiful colours of the changing seasons.
  • 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?

    To get the best deals and availability, book your villa rental in Pienza a few months in advance, especially if you're travelling during the peak season (June-August). You'll find more flexibility and better prices if you book outside of the summer months.
  • 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?

    There are several great hiking trails near Pienza. The Sentiero del Bruco, a circular trail around the town, offers stunning views of the Val d'Orcia. The Sentiero della Via Francigena, a historic pilgrimage route, takes you through picturesque countryside and charming villages.
  • 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 gives you the privacy and flexibility to enjoy your holiday at your own pace. You can cook your own meals, relax in your own space, and enjoy the peace and quiet of the Tuscan countryside. It's a great way to experience the local culture and immerse yourself in the Italian way of life.
  • 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! Pienza is ideally located for exploring other Tuscan gems. You can easily visit Montepulciano, known for its Vino Nobile wine, or Montalcino, famous for its Brunello di Montalcino. Siena, a medieval city with a beautiful historic centre, is also within easy reach.

Popular destinations

Best Pienza villas and holiday homes with parking

Maria Gabriella Holiday Home - Pienza
No reviews

Maria Gabriella Holiday Home

house, Pienza
This independent manor house and cottage is located in Monticchiello, offering excellent access to the Val d’Orcia region, with Triacca Winery and La Foce within a few kilometres.
The property spans 600 square meters, accommodating up to 8 guests across 4 bedrooms with en suite bathrooms, featuring a fully equipped kitchen, air conditioning, and a furnished outdoor area with a barbecue, with on-site parking and breakfast available on request.
A Casa Di Gabri - Pienza
9.5 11 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.
Le Checche - Pienza
9.6 229 reviews

Le Checche

farm, Pienza
Le Checche is a farm stay situated 35 kilometres from Mount Amiata, near Pienza, with Bagno Vignoni 8.7 kilometres away and Bagno San Filippo 16 kilometres distant.
This family-friendly property offers a range of amenities including a swimming pool, hot tub, restaurant, and outdoor play equipment, making it a perfect choice for families seeking a relaxing rural retreat.
Cottage Elena-podere Poggioalsole - Pienza
9.9 120 reviews

Cottage Elena-podere Poggioalsole

house, Montepulciano
Podere Poggio al sole is situated on the outskirts of Montepulciano, offering stunning garden views and easy access to the city centre and its historic landmarks. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house provides a private entrance and terrace, perfect for enjoying the peaceful surroundings. Guests can enjoy a range of amenities including an infinity pool, air conditioning, free Wi-Fi, and a fully equipped kitchen. Outdoor play equipment, hiking trails, and a private bathroom with bathrobes and hairdryers add to the comfort and enjoyment of your stay.

Best Pienza villas and holiday homes with a garden

Casa Il Cipresso - Pienza
9.5 2 reviews

Casa Il Cipresso

house, Montepulciano
Casa Il Cipresso, in Sant'Albino near Montepulciano, enjoys a peaceful setting 2.25km from Montepulciano Terme and offers easy access to Mount Amiata, Bagno Vignoni, and Bagni San Filippo.
This 65 square metre house sleeps five, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, parking, and concierge service.
Podere Le Querci A Charming Cottage In Val D'orcia - Pienza
9.9 69 reviews

Podere Le Querci A Charming Cottage In Val D'orcia

chalet, Trequanda
Podere le Querci, a self-catering apartment near Castelmuzio in the Val d'Orcia, is situated approximately 6km from Trequanda and offers stunning views, close proximity to Montalcino, Montepulciano, and Pienza, and is within easy reach of the A1 motorway.
This one-bathroom property sleeps up to four guests, featuring a king-size bed, sofa bed, and optional children's bed, a functional fireplace, a fully equipped kitchen with fridge and microwave, private parking, a garden within a 6-hectare olive grove, and allows pets; guests can explore the olive grove and sample the organic olive oil produced on-site, and visit the Convent of Saint Anna in Camprena, a filming location for 'The English Patient'.
Villa Banditello, Secluded, Panoramic View Over Montepulciano Valley. - Pienza
9.8 113 reviews

Villa Banditello, Secluded, Panoramic View Over Montepulciano Valley.

apartment, Torrita di Siena
This family-friendly holiday home is located in a peaceful rural setting near Torrita di Siena, just a short drive from the historic Church of St Agnes and the Colonna del Marzocco. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has three bedrooms and can accommodate up to six guests. Guests can enjoy a range of amenities, including a private garden, swimming pool, tennis court, and a fully equipped kitchen with a dishwasher.
La Chiusa Dei Monaci - Pienza
9.1 176 reviews

La Chiusa Dei Monaci

farm, Trequanda
La Chiusa dei Monaci is a farm stay located in Castelmuzio, a small village near Trequanda, just 50 km from both Siena and Arezzo, offering a peaceful escape from the hustle and bustle. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The farm stay offers a 40 square metre, one-bedroom apartment with a fully equipped kitchen, perfect for a family of four. Guests can enjoy the private terrace with stunning views, the garden, and barbecue facilities for al fresco dining.
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