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
9.6 4 reviews

Agriturismo Il Casato - Il Torchio

farm, Pienza
Farm with an excellent rating of 96% based on 4 reviews. This accommodation is located in Pienza.
Services and facilities include a washing machine, air conditioning and an iron. Enjoy free parking with this accommodation in Pienza!
Azienda Agricola Poderuccio - Pienza
9.0 96 reviews

Azienda Agricola Poderuccio

farm, Pienza
Azienda Agricola Poderuccio, a self-catering property in the Val d'Orcia, lies 1km from Pienza's historic centre, offering stunning views featured in the film 'Gladiator'.
This agriturismo comprises four apartments, each approximately 50 square metres, with a restaurant serving farm-fresh Tuscan cuisine, plus mountain bikes for exploring the surrounding countryside and nearby hot springs.
Casa Di Vico, A Due Passi Dal Centro Di Pienza - Pienza
10 6 reviews

Casa Di Vico, A Due Passi Dal Centro Di Pienza

house, Pienza
This Pienza apartment offers a rare generous outdoor space with complimentary parking, situated a short walk from the historic centre of Pienza, a town renowned for its Renaissance architecture.
This three-bedroom flat sleeps six guests and features three en-suite bathrooms, air conditioning throughout, a well-equipped kitchen, and a comfortable living room, providing a convenient base for exploring the Tuscan countryside.

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

Tenuta Santo Pietro - Pienza
9.3 808 reviews

Tenuta Santo Pietro

farm, Pienza
Tenuta Santo Pietro is a working farm located just three miles from the historic town of Pienza, nestled in the Tuscan countryside. The farm enjoys excellent ratings for its location, cleanliness, and overall experience.
The farmhouse dates back to the 13th century and has been beautifully restored, featuring terracotta floors and exposed wooden beams. Guests can enjoy a swimming pool, a restaurant serving traditional Tuscan cuisine, and a range of activities including wine and olive oil tastings, as well as exploring the peaceful gardens.
Casa Valerie - Pienza
9.3 3 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.
Agriturismo Barbi - Pienza
9.1 309 reviews

Agriturismo Barbi

farm, Pienza
Azienda Agricola Barbi is a farmhouse located 8km from Pienza, a charming medieval town known for its Renaissance architecture, and is set within the stunning Val d'Orcia, a UNESCO World Heritage Site famed for its rolling hills and vineyards. The property enjoys excellent ratings for location, cleanliness, and user experience.
The farmhouse offers self-catering apartments with traditional Tuscan features and a fully equipped kitchen. Guests can enjoy a shared garden with BBQ facilities, a tennis court, and free parking and Wi-Fi.
Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.5 64 reviews

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Pienza
Farm listing for 5 guests with an excellent rating of 95% based on 64 reviews. Your accommodation will be based in Pienza.
Services and facilities: a kitchen, a restaurant and a barbecue. Enjoy free parking with this accommodation in Pienza!

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

Vento D’orcia - Pienza
9.8 719 reviews

Vento D’orcia

farm, Pienza
Vento d'Orcia, a farm stay located 16 kilometres from Bagno Vignoni and 50 kilometres from Mount Amiata in the Tuscan countryside, offers a peaceful retreat with stunning garden views and a dedicated children's playground.
This family-friendly property features a restaurant serving authentic Tuscan cuisine, a continental breakfast, and room service, as well as air conditioning, a flat-screen TV with streaming services, a safety deposit box, and a private bathroom with a walk-in shower, hairdryer, and complimentary toiletries.
Villa Agriturismo Il Pratone - Pienza
9.5 11 reviews

Villa Agriturismo Il Pratone

house, Castiglione d'Orcia
Villa Agriturismo Il Pratone, a self-catering holiday home in Castiglione d’Orcia, Tuscany, offers stunning mountain views and easy access to the Tuscan countryside.
This 100m² property sleeps six, boasting two bedrooms, two bathrooms, a well-equipped kitchen with dishwasher, private fenced pool (June-September), high-speed Wi-Fi, on-site parking for three cars, and seasonal homemade produce and wine tastings.
Agriturismo Il Casalino - Pienza
9.6 718 reviews

Agriturismo Il Casalino

farm, Pienza
Agriturismo Il Casalino is a 19th-century farmhouse located in Pienza, a UNESCO World Heritage site, just 39 kilometres from Siena and 47 kilometres from Arezzo, offering stunning views of the Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers independent apartments with a rustic interior design, each with its own entrance. Guests can enjoy a range of amenities including a terrace with panoramic views, a garden, free parking, WiFi, and the option to rent bikes to explore the surrounding area.
Borgo Del Molinello - Pienza
9.2 59 reviews

Borgo Del Molinello

farm, Montepulciano
Borgo del Molinello is a farm stay located in Sant'Albino, a short 10-minute drive from the historic town of Montepulciano, within easy reach of Chianciano Terme and Bagno Vignoni. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The farm stay offers a comfortable 1-bedroom apartment with 2 bathrooms, covering 50 square metres and accommodating up to 2 guests. Enjoy a peaceful rural setting with a swimming pool, garden, terrace, and free parking, as well as a fully equipped kitchen, internet access, and a table tennis table for entertainment.

Best Pienza villas and holiday homes with parking

Agriturismo La Chiusa Tuscany - Pienza
No reviews

Agriturismo La Chiusa Tuscany

house, Torrita di Siena
This luxurious villa is located in Torrita di Siena, just a short drive from the charming town centre and surrounded by rolling hills with stunning views of Montepulciano and Monte Amiata. The villa is situated in a peaceful and secluded location, perfect for a relaxing getaway.
The villa spans 3716 square metres and can accommodate up to 40 guests in its 18 bedrooms and 18 bathrooms. Guests can enjoy a range of amenities, including a swimming pool, spa, garden, and terrace, as well as activities such as wine tours, mountain biking, and horseback riding.
Agriturismo Il Casato Mag-il Vaglio - Pienza
9.8 9 reviews

Agriturismo Il Casato Mag-il Vaglio

gîte, Pienza
Agriturismo Il Casato Mag-il Vaglio is situated near Pienza, just 7km from the Vitaleta Chapel, 9km from the House of the Gladiators, and 10km from Bagno Vignoni, offering stunning mountain views in the heart of the Val d'Orcia. This charming cottage provides a comfortable escape for up to four guests, featuring two bedrooms and a well-equipped kitchen. The property offers a range of amenities including air conditioning, a private garden, parking, and a shared terrace with a barbecue, as well as access to guided wine cellar tours and tastings, electric bike and vintage car rentals, and a delicious breakfast option.
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.
50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.4 21 reviews

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Castiglione d'Orcia
Farm rental for up to 5 people with an excellent rating of 94% based on 21 reviews. Your accommodation will be based in Castiglione d'Orcia.
Services and facilities: a jacuzzi, a kitchen and a barbecue. Take advantage of the Free Parking with this accommodation.

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.

30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
9.4 21 reviews

30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Castiglione d'Orcia
50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Pienza
9.4 19 reviews

50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Montepulciano
Corolle2 - Pienza
9.6 7 reviews

Corolle2

house, Montepulciano
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

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.

Villa Falco-cignella Resort Apartments In Tuscany - Pienza
9.2 5 reviews

Villa Falco-cignella Resort Apartments In Tuscany

house, Torrita di Siena

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.

Manor Villa With Private Pool And Spa Surrounded By Greenery - Pienza
9.2 7 reviews

Manor Villa With Private Pool And Spa Surrounded By Greenery

house, Montalcino
Podere Santaadele - Pienza
8.5 142 reviews

Podere Santaadele

farm, Montepulciano
La Casa Di Emanuela - Pienza
9.5 9 reviews

La Casa Di Emanuela

house, Montepulciano
Villa Il Giardinello - Pienza
No reviews

Villa Il Giardinello

house, Montalcino
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