Vacation Rentals in Pienza

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Pienza holiday rentals
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114 Holiday rentals and Airbnb in Pienza

Discover Exceptional Family Holiday Rentals in Pienza, Italy

Keep the whole group together under one roof with plenty of space to lounge at family holiday rentals in Pienza, Italy.

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.
Residence Hill - Pienza
9.8 148 reviews

Residence Hill

apartment, San Quirico d'Orcia
Residence Hill is a spacious apartment located just 5.3 kilometres from Bagno Vignoni, a charming village known for its natural hot springs, and 45 kilometres from Siena's Piazza del Campo, offering a peaceful retreat in the Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom apartment, spanning 160 square metres, features a fully equipped kitchen, two living rooms, and a private hot tub. Guests can enjoy a range of amenities, including a shared kitchen and lounge, a terrace, a swimming pool, a spa, a tennis court, and free Wi-Fi.
La Violetta Di San Quirico, Centro Storico. - Pienza
9.9 128 reviews

La Violetta Di San Quirico, Centro Storico.

apartment, San Quirico d'Orcia
This San Quirico d'Orcia apartment, boasting panoramic Val d'Orcia views, is situated in the town centre, within easy walking distance of churches and restaurants.
The top-floor flat offers one bedroom, one bathroom, sleeps two guests, includes a fully equipped kitchen with dishwasher, and benefits from free parking.
Palazzo Tombesi Trecci - Pienza
8.9 344 reviews

Palazzo Tombesi Trecci

apartment, Montepulciano
Palazzo Tombesi Trecci is situated in Montepulciano, close to the thermal baths of Montepulciano Terme and within easy reach of the picturesque village of Bagno Vignoni, offering a convenient base for exploring the Tuscan countryside. The apartment consistently receives very good ratings for cleanliness and user experience, and enjoys an excellent location rating.
This apartment offers a comfortable and well-equipped stay, with a kitchen featuring a fridge, freezer, and dishwasher. Guests can enjoy the outdoor space with a terrace or balcony, a peaceful garden, and even scenic views of the surrounding mountains or the nearby lake.

Best Pienza holiday rentals with parking

Podere Lamone A Monticchiello - Pienza
No reviews

Podere Lamone A Monticchiello

apartment, Pienza
This spacious 4-bedroom flat, located in Monticchiello, is situated 11 kilometres from Parco dei Mulini and 42 kilometres from Mount Amiata, with Terme di Montepulciano 13 kilometres away and Bagni San Filippo 23 kilometres distant.
Offering accommodation for up to 12 guests, this 100 square metre residence features air conditioning, WiFi, a dishwasher, and a swimming pool, whilst private parking is also available for convenience.
Bernini's Place - Town Centre Apartment - Pienza
9.9 66 reviews

Bernini's Place - Town Centre Apartment

apartment, San Quirico d'Orcia
This four-bedroom, two-bathroom apartment in San Quirico d'Orcia is centrally located, within easy walking distance of the historic town centre and its shops and cafes.
Sleeping six guests, the property features a spacious living room, a functional kitchen with a large dining table, and parking is provided.
Agriturismo Zampugna - Pienza
9.4 640 reviews

Agriturismo Zampugna

farm, Trequanda
Agriturismo Zampugna is situated in Montefollonico, a charming village just a short drive from Trequanda and approximately 52 miles from Perugia San Francesco d'Assisi Airport. The farm stay has received excellent ratings for its location, cleanliness and overall user experience.
The property offers a peaceful garden and a private entrance for a relaxing stay. Guests can enjoy a swimming pool with stunning views, a terrace, barbecue facilities, a picnic area, a restaurant and free parking.
Villa Campriano 7 By Vacavilla - Pienza
No reviews

Villa Campriano 7 By Vacavilla

house, Pienza
Villa Campriano 7 by VacaVilla, located 45 kilometres from Mount Amiata, is situated 11 kilometres from Bagno Vignoni and 27 kilometres from Bagni San Filippo, offering proximity to natural thermal springs and historical sites such as Palazzo Chigi-Saracini and the National Picture Gallery Siena.
This spacious 250 square metre villa accommodates up to 13 guests across 4 bedrooms and 3 bathrooms, featuring a well-equipped kitchen, two living rooms, a garden, a seasonal outdoor swimming pool, and Wi-Fi, with pets permitted.

Frequently asked questions about holiday rentals in Pienza

  • What are some interesting places to visit in or near Pienza?

    Pienza is a beautiful town, but you also have a lot to see in the surrounding area. The Duomo di Pienza is a must-see, and the Palazzo Piccolomini is a great place to learn about the history of the town. For a day trip, visit the nearby town of Montepulciano, known for its Vino Nobile wine. If you're interested in art, the Museo Diocesano in Pienza is worth a visit.
  • What are the best Airbnb and holiday rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are among the best Airbnb and holiday rentals in Pienza.

  • Which walking or cycling routes are the best in Pienza?

    Pienza is perfect for exploring on foot. The historic centre is small and easily walkable, and there are plenty of charming alleyways to discover. For a longer walk, try the Sentiero della Val d'Orcia, which offers stunning views of the Tuscan countryside. If you prefer cycling, the Val d'Orcia is also great for a leisurely bike ride, with gentle hills and picturesque landscapes.
  • What are the most popular Airbnbs in Pienza?

    Among the Airbnbs in Pienza, The Cedar House, La Dimora Di Pienza Family 2 Rooms and Panoramic Apaertment Val D'orcia are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Pienza?

    Pienza is a great base for exploring the Val d'Orcia, a UNESCO World Heritage Site. You can go hiking or mountain biking in the surrounding hills, or enjoy a picnic in one of the many vineyards. There are also opportunities for horseback riding and hot air ballooning in the area.
  • What are the best holiday rentals with a pool in Pienza?

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

  • What other towns or cities can be easily accessed from Pienza?

    Pienza is well-connected to other towns and cities in Tuscany. You can easily reach Siena, Florence, and Rome by car or train. For a day trip, visit the charming hilltop town of Montepulciano, just a short drive away. You can also easily reach the beautiful Lake Trasimeno, a popular destination for swimming and watersports.
  • What are the best rentals for families and kids in Pienza?

    The best rentals for families and kids in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo.

  • What amenities are commonly available in vacation rentals in Pienza?

    Most vacation rentals in Pienza offer basic amenities like a kitchen, bathroom, and Wi-Fi. Many also have a private garden or terrace, and some even have a swimming pool. It's always a good idea to check the listing for specific details about the amenities offered.
  • What are the best rentals or Airbnbs with a jacuzzi in Pienza?

    The best holiday rentals or Airbnb with a jacuzzi in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and Poggio Ai Gelsi.

  • What time of year is best to rent a vacation rental Pienza?

    The best time to visit Pienza is in the spring or autumn, when the weather is mild and the crowds are smaller. Summer can be hot and crowded, while winter can be cold and wet. However, if you're looking for a quieter experience, winter can be a good time to visit.

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Discover Holiday Rentals with a Balcony in Pienza, Italy

Watch the local morning bustle with a fresh breeze at holiday rentals featuring an outdoor balcony in Pienza, Italy.

La Terrazza Sulla Val D'orcia - Pienza
9.8 81 reviews

La Terrazza Sulla Val D'orcia

apartment, Castiglione d'Orcia
"La Terrazza sulla Val d'Orcia" is located in Castiglione d'Orcia, a charming village in the heart of Tuscany, just 40 kilometres from Pienza, 26 kilometres from Montepulciano and Montalcino, and 5 kilometres from the Bagno Vignoni Spa centre. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom apartment offers 75 square metres of space, comfortably accommodating up to four guests. The apartment features a fully equipped kitchen, a terrace with stunning views of the Val d'Orcia, a garden, parking, and free Wi-Fi, making it the perfect base for exploring the region.
90 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Pienza
No reviews

90 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Torrita di Siena
Podere Villa Rosa, a pet-friendly apartment in Torrita di Siena, Tuscany, offers easy access by car to nearby towns such as Siena, Montepulciano, and Pienza.
This 90 square metre self-catering flat sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, a private balcony with barbecue, and on-site parking.
90 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

90 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Torrita di Siena
This Tuscan farmhouse, 1.3 km from Montefollonico and 7 km from Montepulciano, boasts panoramic views of the Val d'Orcia, San Biagio temple, Monte Amiata, and the surrounding hills.
The 90 square metre property sleeps six, offering three bedrooms, two bathrooms, a fully equipped kitchen with fridge, Wi-Fi, a terrace, garden, and washing machine, plus a barbecue and a baby bed.
Appartamenti Il Leone - Pienza
8.0 188 reviews

Appartamenti Il Leone

apartment, Pienza
Appartamenti Il Leone is situated in Pienza, 15 kilometres from Bagno Vignoni and 45 kilometres from Mount Amiata, with Montepulciano Terme 16 kilometres away and Bagni San Filippo 26 kilometres distant.
This 55 square metre apartment offers two bedrooms and one bathroom, featuring a fully equipped kitchen, a terrace with city views, free WiFi, and on-site parking, with a swimming pool and concierge service available for guests.

Compare Pet-Friendly Holiday Rentals in Pienza, Italy

Let your dog stretch their legs and explore a new neighborhood alongside you at pet-friendly holiday rentals in Pienza, Italy.

Schivanoia 2 - Pienza
9.6 109 reviews

Schivanoia 2

apartment, San Quirico d'Orcia
This four-bedroom apartment in Bagno Vignoni, a short walk from the town's centre and approximately 19 kilometres from Bagno San Filippo, offers easy access to San Quirico d'Orcia and other Tuscan destinations.
Schivanoia 1 boasts a spacious layout with a living room, fully equipped kitchen (including fridge and dishwasher), two bathrooms, outdoor seating, free Wi-Fi, private parking, and a fireplace; sleeping up to eight guests.
The House Of Two Vineyards - Pienza
No reviews

The House Of Two Vineyards

apartment, San Quirico d'Orcia
This one-bedroom flat in San Quirico d'Orcia is located within a 5-minute walk of Horti Leonini gardens and Palazzo Chigi, and a 13-minute drive from the historic centre of Pienza and Val di Chiana.
This apartment offers WiFi, modern bathroom amenities including a bidet, heating, toiletries, towels, and a hairdryer, and accommodates up to three guests with pets welcome.
A Casa Di Gabri,  Accoglienza E Semplicità - Pienza
10 15 reviews

A Casa Di Gabri, Accoglienza E Semplicità

apartment, Torrita di Siena
This detached villa near Montefollonico, Siena province, offers easy access to Pienza (5km), Montepulciano (7km), and Montalcino (20km), nestled near hiking trails including routes for L'Eroica and the Via Francigena.
The two-bedroom, two-bathroom property sleeps five, boasting a private garden, fully equipped kitchen with dishwasher, and excellent guest reviews, making it ideal for families exploring Tuscany.
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.
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