Villas and Holiday homes in Pienza

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Pienza holiday homes
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19 Villa rentals in Pienza

Browse Holiday Homes near the Historic Centre in Pienza

Stay near top-rated restaurants and major sights with central holiday homes in Pienza city centre.

Podere San Gregorio - Pienza
9.0 5 reviews

Podere San Gregorio

farm, Pienza
Podere San Gregorio, a family-run farm stay near Pienza, Tuscany, offers a tranquil escape less than 1 kilometre from Pienza's historic centre and the Val d'Orcia Natural Park.
This one-bedroom self-catering apartment features a rustic-chic interior with Tuscan antique furniture, a fully equipped kitchen including a dishwasher, and access to on-site amenities such as wine and olive oil tasting, plus participation in farm activities like winemaking and truffle hunting.
Agriturismo Il Casato - Il Torchio - Pienza
9.4 47 reviews

Agriturismo Il Casato - Il Torchio

farm, Pienza
Agriturismo il casato - il torchio is located in Pienza, just 5.4km from the thermal baths of Bagno Vignoni and 43km from Mount Amiata, offering a peaceful escape in the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom farmhouse spans 70 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a terrace, a garden, free Wi-Fi, and parking, plus table tennis, and opportunities for cycling and hiking in the surrounding area.
Agriturismo Colombaiolo - Pienza
9.2 69 reviews

Agriturismo Colombaiolo

farm, Pienza
Agriturismo Colombaiolo, a 15th-century farmhouse, is situated 0.5km from Pienza's centre in the Val d'Orcia, a UNESCO World Heritage site.
This one-bedroom, one-bathroom property offers guests a complimentary Italian breakfast, on-site parking, and the opportunity to sample the owners' homemade olive oil, all within its 30-hectare estate of olive groves, vineyards, and vegetable gardens.
Agriturismo Il Casato - Il Torchio - Pienza
10 7 reviews

Agriturismo Il Casato - Il Torchio

gîte, Pienza
This Pienza holiday apartment, near the Vitaleta Chapel (7km), offers stunning mountain views and easy access to Val d'Orcia landmarks such as the House of Gladiators (9km), Bagno Vignoni (10km), Montepulciano (15km), and Montalcino (25km).
The 70m² self-catering property sleeps four, features a well-equipped kitchen, a private outdoor space with barbecue, and provides amenities including Wi-Fi, air conditioning, and a washing machine; guided winery tours and e-bike rentals are available.

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

95 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests - Pienza
9.7 176 reviews

95 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests

farm, Pienza
Farm rental for 7 guests with an excellent rating of 97% based on 176 reviews. You will be located in Pienza.
Services and facilities include a fridge, a tennis court and a washing machine. This accommodation in Pienza also has a terrace!
Villa Il Moro - Pienza
8.8 8 reviews

Villa Il Moro

house, Montalcino
Villa il Moro, a spacious 550 square metre property in Montalcino, Tuscany, is situated 45km from Siena’s Piazza del Campo and within easy reach of other Tuscan towns such as Bagno Vignoni.
This five-bedroom, six-bathroom villa sleeps up to 19 guests and boasts a private swimming pool, terrace, garden, free Wi-Fi, and ample parking, ideal for large families or groups seeking a self-catering holiday with access to hiking and cycling in the Tuscan countryside.
Agriturismo Poggio Tobruk - Pienza
9.5 611 reviews

Agriturismo Poggio Tobruk

farm, Pienza
Agriturismo Poggio Tobruk is situated in the Val d'Orcia Park, a UNESCO World Heritage Site, just 10 kilometres from the historic town of Pienza, offering stunning views of the olive groves and Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers self-catering apartments with a fully equipped kitchenette, a spacious dining room for enjoying traditional Tuscan cuisine, and a terrace or balcony for relaxing. Guests can enjoy a range of amenities including a tennis court, a garden, and free parking, as well as purchase authentic olive oil produced directly on the farm.
Palazzo Massaini - Cavarciano - Pienza
9.2 1008 reviews

Palazzo Massaini - Cavarciano

farm, Pienza
Palazzo Massaini - Cavarciano is located in the Tuscan countryside, 5 kilometres from the charming town of Pienza, close to the San Biagio Church and 18 kilometres from Chianciano Terme. This farm stay has consistently received excellent ratings for its location, cleanliness and overall experience.
The farm offers a variety of accommodation options, including rooms and apartments, to suit different needs and group sizes. Guests can enjoy a delicious Italian breakfast, relax by the swimming pool at a nearby partner property, and benefit from amenities such as free parking, Wi-Fi and air conditioning.

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, and the Palazzo Piccolomini, a grand palace offering beautiful views of the Val d'Orcia. For a taste of local life, head to the Piazza Pio II, the heart of Pienza, where you can enjoy the local atmosphere. Just a short drive away, you can explore the enchanting medieval village of Monticchiello, known for its charming streets and annual theatre festival.
  • What are the best holiday homes in Pienza?

    Among the holiday homes 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 wild boars, deer, and foxes. You might also spot birds of prey like buzzards and kestrels soaring above the rolling hills. If you're lucky, you might even catch a glimpse of a rare Italian wolf, but remember to keep a safe distance.
  • What are the best holiday homes with a pool in Pienza?

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

  • What is the best time to visit Pienza?

    Spring and autumn are the best times to visit Pienza, as the weather is mild and the crowds are smaller. You can enjoy the beautiful scenery without the summer heat or winter chill. The countryside is particularly stunning in autumn, when the leaves turn vibrant shades of red, orange, and yellow.
  • What are the best holiday homes with a jacuzzi in Pienza?

    The best holiday homes 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 outside of peak season, which is typically July and August. If you're flexible with your travel dates, you can find great deals on villa rentals in the shoulder seasons, such as April-May or September-October.
  • What are the best holiday homes for families and kids in Pienza?

    The best holiday homes 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 winds through the Val d'Orcia, offers breathtaking views of the rolling hills and vineyards. For a shorter hike, you can explore the trails around the Monte Amiata, a volcanic mountain with stunning views of the surrounding countryside. Remember to wear sturdy hiking shoes and bring plenty of water.
  • What are the best pet friendly holiday homes in Pienza?

    The best pet friendly holiday homes 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 gives you the freedom and privacy to enjoy your holiday at your own pace. You can cook your own meals, relax in your private garden, and enjoy the peace and quiet of the countryside. It's also a great option for families or groups of friends who want to spend quality time together.
  • What are the best holiday homes with parking in Pienza?

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

  • Are there popular destinations near Pienza?

    Pienza is a great base for exploring the region of Tuscany. Within a short drive, you can visit the charming hilltop town of Montepulciano, famous for its Vino Nobile wine, or the historic city of Siena, known for its stunning Piazza del Campo. You can also explore the beautiful vineyards and olive groves of the Val d'Orcia, a UNESCO World Heritage site.

Popular destinations

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, a short distance from both the scenic Mount Amiata (48km) and the thermal baths of Montepulciano Terme (10km), offering a tranquil escape in the Tuscan countryside. The property has received very good user, location and excellent cleanliness ratings.
The villa is spread over 157 square metres and offers four bedrooms and four bathrooms. Guests can enjoy a private pool, open-air bath, a spa, a fully equipped kitchen, a terrace, a garden, air conditioning, free Wi-Fi, and free parking.
Agriturismo Palazzo Conti - B - Pienza
7.9 88 reviews

Agriturismo Palazzo Conti - B

farm, San Quirico d'Orcia
Agriturismo Palazzo Conti - B is situated in Pienza, a charming town in the Val d'Orcia, just 22 miles from Siena and 29 miles from Arezzo, making it an ideal base for exploring the Tuscan countryside. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The farm offers comfortable accommodation for up to four guests, with a fully equipped kitchen and a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace or in the garden, and benefit from free Wi-Fi and parking.
"Agriturismo Piandimaggio  In Esclusiva " - Pienza
9.7 330 reviews

"Agriturismo Piandimaggio In Esclusiva "

gîte, Pienza
This charming gîte is located in the Val d'Orcia, just a short distance from the picturesque town of Pienza and the thermal baths of Bagno Vignoni, with views of the majestic Monte Amiata. The property has received excellent user ratings for its location, cleanliness, and overall experience.
The farmhouse offers three apartments, perfect for families or groups of friends, with a total capacity of 14 guests. Guests can enjoy a private swimming pool, a spacious garden with a BBQ, and panoramic views of the surrounding countryside.
Le Sorbelle D'orcia - Pienza
9.5 153 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.

Best Pienza villas and holiday homes with parking

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.
57 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Pienza
10 1 review

57 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Pienza
Farm for up to 2 guests with an excellent rating of 100% based on 1 reviews. This accommodation is based in Pienza.
Facilities and services: a fridge, a barbecue and a wheelchair friendly access. You can bring your favourite pets this accommodation!
Villa Falco-cignella Resort Apartments In Tuscany - Pienza
No reviews

Villa Falco-cignella Resort Apartments In Tuscany

house, Trequanda
Villa Falco-Cignella Resort Apartments in Osteria Delle Noci, Tuscany, is located 17.7 kilometres from Montepulciano Terme and 24.1 kilometres from Bagno Vignoni, offering proximity to notable thermal spa towns.
This 142 square metre air-conditioned villa accommodates up to seven guests in two bedrooms, featuring a fully equipped kitchen, a balcony with outdoor furniture, complimentary WiFi, and an outdoor swimming pool, with parking and pets allowed.
Agriturismo Selvoli - La Scuola - Pienza
9.9 74 reviews

Agriturismo Selvoli - La Scuola

cabin, Pienza
This pet-friendly studio apartment, a former schoolhouse near Selvoli, is a short distance from Pienza.
The self-contained property offers a well-equipped kitchenette, bathroom with shower, a French-size bed (190x160cm), private garden, and sleeps two, ideal for couples seeking a peaceful base to explore Pienza.

Compare Holiday Homes with a Pool in Pienza

Every holiday home with a pool in Pienza ensures that a proper swim in the heart of the city is always an effortless option.

Agriturismo Castello Di Spedaletto - Pienza
9.8 371 reviews

Agriturismo Castello Di Spedaletto

farm, Pienza
Il Colombaiolo - Pienza
9.1 154 reviews

Il Colombaiolo

farm, Trequanda
Palazzo Massaini | Castle Suites In Valdorcia - Pienza
No reviews

Palazzo Massaini | Castle Suites In Valdorcia

castle, Pienza
Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza

Find the Best Luxury Holiday Homes in Pienza

Upscale holiday homes in Pienza offer a memorable stay with premium amenities designed for those who appreciate the finer things.

Santa Margherita - Pienza
9.5 14 reviews

Santa Margherita

house, Castiglione d'Orcia

Browse Holiday Homes with a Hot Tub in Pienza

Returning to a hot tub after a day in the city is a luxury provided by these premier holiday homes in Pienza.

Monastero Sant'anna In Camprena - Pienza
9.6 430 reviews

Monastero Sant'anna In Camprena

farm, Pienza
Agriturismo Belagaggio - Pienza
9.5 522 reviews

Agriturismo Belagaggio

farm, Torrita di Siena
50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.4 21 reviews

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Castiglione d'Orcia
Suite Gioconda A Pienza - Pienza
9.6 31 reviews

Suite Gioconda A Pienza

house, Pienza
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