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.

Suite Gioconda A Pienza - Pienza
9.6 29 reviews

Suite Gioconda A Pienza

house, Pienza
Suite Gioconda in Pienza offers a self-catering property near Bagno Vignoni (12.7km) and Mount Amiata (43.5km), popular tourist destinations in Tuscany.
This 80-square-metre house features two bedrooms, one bathroom with a hot tub, a private garden with outdoor seating, free Wi-Fi, free parking, and sleeps up to seven guests.
Colombaiolo - Pienza
9.0 4 reviews

Colombaiolo

farm, Pienza
Agriturismo Colombaiolo is a farm stay located 500 meters from Pienza and 400 meters from the Pieve di Corsignano church, offering panoramic views of Pienza, Val d'Orcia, and Monte Amiata from its late 1400s stone structure. This accommodation provides internet, air conditioning, and parking, and features spacious rooms furnished in traditional Tuscan style, with breakfast highlighting local produce and opportunities to observe farm and wild animals within a nature reserve.
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.
Apartment "Agriturismo Il Casato Mag-il Vaglio" With Mountain View, Terrace And Wi-fi - Pienza
10 2 reviews

Apartment "Agriturismo Il Casato Mag-il Vaglio" With Mountain View, Terrace And Wi-fi

farm, Pienza
This Pienza farm stay, a 70 square metre (753 square foot) self-catering cottage, is a 10-minute walk from landmarks including Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile.
Offering two bedrooms, one bathroom, sleeping up to four guests, it features air conditioning, a terrace, garden, parking, and barbecue facilities, plus a fully equipped kitchen including a fridge and microwave.

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

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.
Agriturismo Castello La Grancia Di Spedaletto - Pienza
9.5 881 reviews

Agriturismo Castello La Grancia Di Spedaletto

farm, Pienza
Agriturismo Castello La Grancia di Spedaletto is located in the Tuscan countryside, 10 kilometres from Pienza and a 40-minute drive from Montepulciano. It has received excellent ratings for location, cleanliness, and overall guest experience.
This charming rural retreat offers a one-bedroom property that can accommodate two guests. It features a range of amenities, including a swimming pool, a garden, and BBQ facilities, as well as free Wi-Fi, air conditioning, and a fully equipped kitchen.
69 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Pienza
10 1 review

69 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Pienza
Farm for 4 guests with an excellent rating of 100% based on 1 reviews. You will stay in Pienza.
Services and facilities include a kitchen, a barbecue and free parking. Take advantage of the garden in this accommodation!
Agriturismo San Biagio - Pienza
8.7 92 reviews

Agriturismo San Biagio

farm, Montepulciano
Agriturismo San Biagio is a short distance from the thermal baths of Montepulciano Terme, just 5 kilometres away, and 47 kilometres from Mount Amiata, offering a peaceful escape in the Tuscan countryside. It has received excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers a one-bedroom unit with a 40 square metre floor area, suitable for up to three guests. Amenities include a shared kitchen, free Wi-Fi, a picnic area, and private parking, as well as welcome treats and a private entrance.

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

Agriturismo Podere La Paolina - Residenza Di Charme - Pienza
9.1 77 reviews

Agriturismo Podere La Paolina - Residenza Di Charme

farm, Torrita di Siena
Podere La Paolina is a farm stay situated in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering easy access to the Valdichiana and the beautiful Tuscan countryside. The property has received excellent ratings for cleanliness and location, making it a popular choice for travellers seeking a relaxing escape.
The accommodation offers a choice of rooms and self-catering apartments, all with private entrances and soundproofing for a peaceful stay. Guests can enjoy stunning garden views, a swimming pool, and a restaurant serving delicious Italian cuisine, as well as take advantage of the on-site yoga sessions, bicycle rental, and convenient amenities like free Wi-Fi and parking.
Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany - Pienza
9.6 20 reviews

Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany

house, Pienza
This charming house is located in a peaceful rural setting, just 15 kilometres from Pienza's main attractions, including Piazza delle Sorgenti, Art Studio di Adelina Quadri, and La Foce. It has received excellent reviews from previous guests.
The house spans 400 square metres and comfortably accommodates up to 20 guests. The property features a private pool, a spacious garden, and a barbecue area, perfect for relaxing and enjoying the Tuscan sunshine.
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.
Agriturismo Vergelle - Pienza
9.2 65 reviews

Agriturismo Vergelle

farm, Montalcino
Agriturismo Vergelle is situated in the Crete Senesi, a 30-minute drive from San Quirico d’Orcia and 19 kilometres from the Abbey of Monte Oliveto Maggiore, offering a peaceful escape in the Tuscan countryside. The property consistently receives very good ratings for its location, cleanliness, and overall experience.
The apartments are decorated in a rustic style with wood-beamed ceilings and terracotta floors, creating a charming and authentic Tuscan ambiance. Guests can enjoy a range of amenities including a swimming pool, a garden with BBQ facilities, and a restaurant serving fresh, locally sourced ingredients.

Best Pienza villas and holiday homes with parking

La Casa Di Vignoni Alto - Pienza
8.7 63 reviews

La Casa Di Vignoni Alto

house, San Quirico d'Orcia
La Casa di Vignoni Alto is a holiday home located in the village of Bagno Vignoni, 1.9 kilometres from the famous thermal baths and a short drive from other attractions such as Bagni San Filippo (19 kilometres) and Montepulciano Terme (29 kilometres).
The 250 square metre property features two bedrooms, two bathrooms, and can accommodate up to nine guests, and offers amenities such as a fully equipped kitchen, a garden, a tennis court, and free Wi-Fi.
Tenuta Santavenere - Pienza
No reviews

Tenuta Santavenere

farm, Montepulciano
Tenuta Santavenere, a farm stay in Triacca, is located 2.9 kilometres from Montemercurio and 17.7 kilometres from Parco dei Mulini, offering convenient access to local attractions.
This family-friendly property accommodates up to three guests in one bedroom and features air conditioning, WiFi, a garden, and on-site parking, with pets welcome.
80 M² House ∙ 2 Bedrooms ∙ 3 Guests - Pienza
No reviews

80 M² House ∙ 2 Bedrooms ∙ 3 Guests

house, Torrita di Siena
This detached dwelling is located in the medieval village of Montefollonico, a few kilometres from Montepulciano and Pienza, and close to thermal spa regions.
This 80 square metre property sleeps 3, with 2 bedrooms and 1 bathroom, offering free parking 50 metres away and Wi-Fi, with an option for a fourth bed at extra cost.
Dimore Di Sant'albino Montepulciano - Pienza
8.6 21 reviews

Dimore Di Sant'albino Montepulciano

house, Montepulciano
Dimore di Sant'Albino is a property located in Sant'Albino, a 6-minute walk from Montepulciano Terme and 22.5 kilometres from the natural thermal springs of Bagno Vignoni.
This one-bedroom apartment offers Wi-Fi, a kitchen equipped with a fridge, microwave, and dishwasher, and a balcony, with opportunities for cycling and hiking nearby.

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.

90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Pienza
No reviews

90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Torrita di Siena
Podere Pratovecchio 14&2, Emma Villas - Pienza
8.9 3 reviews

Podere Pratovecchio 14&2, Emma Villas

house, Torrita di Siena
Villa Aquila-cignella Resort Acommodation Tuscany - Pienza
9.0 1 review

Villa Aquila-cignella Resort Acommodation Tuscany

house, Trequanda
Agriturismo Il Gonzeto, Montepulciano - Pienza
9.0 345 reviews

Agriturismo Il Gonzeto, Montepulciano

farm, Montepulciano

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.

Apartment "Agriturismo Il Casato Mag-il Torchio" With Mountain Views, Terrace And Wi-fi - Pienza
10 5 reviews

Apartment "Agriturismo Il Casato Mag-il Torchio" With Mountain Views, Terrace And Wi-fi

farm, Pienza

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.

Villa Montepulciano Vineyard - Pienza
No reviews

Villa Montepulciano Vineyard

house, Montepulciano
Podere Bagnolo 8 Emma Villas - Pienza
No reviews

Podere Bagnolo 8 Emma Villas

house, Pienza
Agriturismo Belagaggio - Pienza
9.5 521 reviews

Agriturismo Belagaggio

farm, Torrita di Siena
240 M² House ∙ 4 Bedrooms ∙ 10 Guests - Pienza
8.8 20 reviews

240 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Castiglione d'Orcia
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