Holiday Rentals in Pienza

69 available vacation rental offers

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Pienza holiday rentals
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Pienza holiday rentals: compare the best deals

Best family friendly Pienza holiday rentals

Among the 69 accommodations in Pienza, here are the 4 best family friendly rentals

Casa Vacanze Oliviera Pienza - Pienza
9.6 21 reviews
Pienza
07/19 – 07/23
HK$1760/nighttotal: HK$7040 (4 )

Casa Vacanze Oliviera Pienza

1 2
apartment , Pienza
This one-bedroom apartment is conveniently located near Pienza, just a short drive from popular destinations like Bagno Vignoni, Montepulciano Terme, and Bagni San Filippo, allowing you to easily explore the Tuscan countryside. The apartment has received very good ratings for cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The flat is 35 square metres in size and features a fully equipped kitchenette, free Wi-Fi, and comfortable amenities like towels, bed linen, and a hairdryer. You can enjoy activities like fishing and hiking in the surrounding area, and pets are welcome.
Cottage Le Pozze - Pienza
8.9 22 reviews
Pienza
08/16 – 08/19
HK$17728/nighttotal: HK$53184 (3 )

Cottage Le Pozze

7 13
chalet , Sinalunga
Cottage Le Pozze is located in Sinalunga, just 39 kilometres from Piazza Grande and 23 kilometres from Montepulciano Terme, making it an ideal base for exploring the beautiful Tuscan countryside. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
This charming chalet offers a comfortable and well-equipped space for your stay. The property boasts a range of amenities, including a private pool, outdoor fireplace, fully equipped kitchenette, free bikes, and a shared lounge, ensuring a relaxing and enjoyable experience.
Casa Belmonte - Pienza
9.9 151 reviews
Pienza
06/27 – 06/28
HK$1703/nightfor 1 night

Casa Belmonte

1 4
apartment , Montepulciano
This recently renovated flat is located in the heart of Montepulciano, just 600 metres from the Piazza Grande and 400 metres from the Porta al Prato, offering easy access to the town's attractions. The property has received excellent ratings for location, cleanliness and user experience.
The apartment has a spacious open-plan living area with a kitchenette, ideal for families or groups of up to four people. It comes equipped with modern amenities like a dishwasher, microwave, coffee maker, TV, and free Wi-Fi, ensuring a comfortable and convenient stay.
Agriturismo Villa Mazzi - Pienza
9.9 154 reviews
Pienza
07/19 – 07/23
HK$1332/nighttotal: HK$5328 (4 )

Agriturismo Villa Mazzi

1 2
farm , Montepulciano
Agriturismo Villa Mazzi is situated in the Tuscan countryside, 30 kilometres from Castiglione del Lago on Lake Trasimeno and a one-hour drive from Arezzo. This farm stay has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The self-catering apartments offer a peaceful retreat in a rustic setting. Guests can enjoy a garden with barbecue facilities, homemade olive oil, jam, and honey, and free Wi-Fi access.

Best Pienza holiday rentals with parking

Agriturismo Podere La Paolina - Residenza Di Charme - Pienza
9.3 76 reviews
Pienza
08/13 – 08/17
HK$6243/nighttotal: HK$24972 (4 )

Agriturismo Podere La Paolina - Residenza Di Charme

3 6
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.
La Colonna Di Montisi - Pienza
9.3 3 reviews
Pienza
06/27 – 06/28
HK$2519/nightfor 1 night

La Colonna Di Montisi

1 4
apartment , Montalcino
La Colonna di Montisi apartment is located in the village of Montisi, approximately 22.5km from both Bagno Vignoni and Montepulciano Terme, offering easy access to the Val d'Orcia.
This 87 square metre self-catering flat sleeps 13 guests and includes a fully equipped kitchen, air conditioning, free Wi-Fi, and private parking.
La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany - Pienza
9.8 76 reviews
Pienza
06/26 – 06/29
HK$2193/nighttotal: HK$6579 (3 )

La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany

2 4
house , Pienza
La CoCCa Luxury Villa is situated in Monticchiello, a charming village in the Tuscan countryside, just a short drive from the historic towns of Montepulciano Terme and Bagno Vignoni. The villa has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom villa comfortably accommodates up to four guests and offers a fully equipped kitchen, air conditioning, and a private garden. Guests can enjoy the peaceful surroundings, explore the nearby towns and countryside by bicycle, and relax in the villa's spa.
108 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Pienza
9.1 15 reviews
Pienza
07/09 – 07/19
HK$1237/nighttotal: HK$12370 (10 )

108 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 3
apartment , Trequanda
This Tuscan holiday apartment, near Castelmuzio, offers breathtaking views of the countryside and is conveniently located for exploring Lake Trasimeno and regional national parks, approximately 30-40km away.
The 108-square-metre property boasts two bedrooms, two bathrooms, and sleeps four, featuring a fully equipped kitchen with dishwasher, a swimming pool, parking, and a wonderful terrace with scenic views; pets are welcome.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza itself is a must-see, with its stunning Renaissance architecture and the iconic Piazza Pio II. Just outside of town, you can visit the Corsignano Castle, a 14th-century fortress, or the charming village of Monticchiello, known for its annual theatrical performances.
  • What are the best Airbnb and vacation rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are the most popular Airbnb and vacation rentals in Pienza among travelers.

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

    The Val d'Orcia, a UNESCO World Heritage Site, offers some beautiful walks and bike rides. You can follow the Via Francigena, an ancient pilgrimage route, or explore the rolling hills and vineyards on a more leisurely cycle. The panoramic views from the top of Monte Amiata are also worth the climb.
  • 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?

    Hiking, cycling, and horseback riding are popular activities in the area. If you are looking for something more adventurous, you can try paragliding from the top of Monte Amiata or go rock climbing in the nearby Val d'Orcia.
  • What are the best vacation rentals with a pool in Pienza?

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

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

    Pienza is well-connected to other Tuscan towns. You can easily visit Siena, Montepulciano, and San Quirico d'Orcia by car or bus. For a day trip, consider visiting the charming medieval town of Montalcino, known for its Brunello di Montalcino wine.
  • 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?

    Many vacation rentals in Pienza offer amenities like Wi-Fi, air conditioning, and private parking. Some rentals also have kitchens, laundry facilities, and outdoor spaces like patios or gardens.
  • What are the best rentals or Airbnbs with a jacuzzi in Pienza?

    The best vacation 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?

    Spring and autumn are generally the best times to visit Pienza, as the weather is mild and the crowds are smaller. Summer can be hot and crowded, while winter can be chilly and rainy.
  • What are the local dishes in Pienza region?

    Pienza is famous for its Pecorino cheese, made from sheep's milk. Try the Pecorino di Pienza DOP, a protected designation of origin cheese. Other local specialties include the ribollita, a hearty bread soup, and the pici, a thick hand-rolled pasta.

Destinations nearby

Best Pienza holiday rentals with a balcony

Debby Appartamenti - Pienza
9.3 83 reviews
Pienza
06/27 – 06/28
HK$1595/nightfor 1 night

Debby Appartamenti

2 4
apartment , Montepulciano
Debby Appartamenti, a two-bedroom apartment in Montepulciano, is conveniently located 5.8km from Montepulciano Terme, offering easy access to the thermal baths and within easy driving distance of Bagno Vignoni (21km) and Bagni San Filippo (29km).
This self-catering flat features a fully equipped kitchen with fridge and microwave, a private terrace, free Wi-Fi, air conditioning, parking, and a bathroom with bidet and hairdryer; sleeping up to four guests, it’s ideal for exploring Tuscany's thermal areas.
Villa Falco - Pienza
Pienza
07/10 – 07/11
HK$15130/nightfor 1 night

Villa Falco

2 2
house , Trequanda
Villa Falco is situated in Trequanda, a village in Tuscany, approximately 18 kilometres from Montepulciano Terme.
This two-bedroom chalet sleeps up to eight guests and offers a fully equipped kitchen, a private pool, and a garden with a terrace, all within a 142 square metre living space.
Chez Anna - Pienza
8.7 9 reviews
Pienza
07/25 – 07/28
HK$1717/nighttotal: HK$5151 (3 )

Chez Anna

2 3
apartment , San Quirico d'Orcia
Chez Anna, a holiday flat in Bagno Vignoni, is located 1.6 kilometres from the town centre and 23 miles from Mount Amiata.
This 120 square metre, two-bedroom holiday flat accommodates up to 11 guests, featuring a fully equipped kitchen, a private terrace, and is a mile from the Bagno Vignoni thermal baths.
Hotel Apartment "Quercia" With Shared Pool & Wi-fi - Pienza
Pienza
09/16 – 09/19
HK$2409/nighttotal: HK$7227 (3 )

Hotel Apartment "Quercia" With Shared Pool & Wi-fi

2 4
apartment , Trequanda
This Trequanda residence is located in the Valdichiana region, offering convenient access to Siena (approximately 1 hour's drive), Pienza (approximately 50 kilometres drive), and Florence (approximately 1.5 hours' drive).
This 86 square metre flat provides accommodation for up to four guests in two bedrooms and two bathrooms, featuring a private terrace, balcony, Wi-Fi, air conditioning, and access to a shared swimming pool, with parking available and optional wine tastings and cooking classes.

Best pet friendly Pienza holiday rentals

Among the 69 accommodations in Pienza, here are the 4 best pet friendly rentals

Il Podere Di Casa Rossa - Pienza - Pienza
9.9 24 reviews
Pienza
09/16 – 09/19
HK$3242/nighttotal: HK$9726 (3 )

Il Podere Di Casa Rossa - Pienza

1 4
apartment , Pienza
This charming farmhouse apartment is situated just outside Pienza, a short walk from the historic town centre, offering easy access to its restaurants, shops and attractions. The property has received excellent ratings for its cleanliness, location and overall experience, making it a popular choice for travellers.
The apartment comprises four suites, comfortably accommodating up to eight guests, providing ample space for families or groups. Guests can enjoy a well-equipped kitchen, a cosy fireplace, a private garden and stunning views of the Val d'Orcia and Mount Amiata.
Dolce Dormire - Pienza
8.9 13 reviews
Pienza
06/27 – 06/28
HK$1812/nightfor 1 night

Dolce Dormire

2 4
resort , Montepulciano
The Dolce Dormire apartment is located in the Tuscan countryside, just 4 kilometres from the charming hilltop town of Montepulciano, surrounded by vineyards and olive groves. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment has two bedrooms and a living room, comfortably accommodating up to six people. Guests can enjoy a private spa, an outdoor swimming pool, and a fitness centre, as well as easy access to the town's historic centre, renowned wineries, and cultural attractions.
Locanda In Tuscany - Pienza
9.4 131 reviews
Pienza
07/28 – 07/31
HK$12924/nighttotal: HK$38772 (3 )

Locanda In Tuscany

3 5
farm , Castiglione d'Orcia
The Locanda in Tuscany is a rural retreat situated just 3.1 miles from the charming town of Castiglione d'Orcia and 16 miles from the historic Montepulciano, making it an ideal base for exploring the beautiful Tuscan countryside. This farm stay consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers a range of accommodation options, each featuring charming wood-beamed ceilings and a choice of bed linens. Guests can enjoy the on-site restaurant, relax by the outdoor pool and garden, or participate in activities like cooking classes, horse riding, and mushroom picking.
Casa Della Fonte - Pienza
9.0 343 reviews
Pienza
07/28 – 07/31
HK$1860/nighttotal: HK$5580 (3 )

Casa Della Fonte

1 5
apartment , San Quirico d'Orcia
Casa della Fonte is a self-catering apartment located in San Quirico d'Orcia, a short distance from the picturesque village centre and close to Mount Amiata and Fontebranda. The apartment has received excellent ratings for location, cleanliness, and overall user satisfaction.
The apartment offers a private entrance and a peaceful garden where you can relax after exploring the region. It is fully equipped with modern amenities, including air conditioning, a flat-screen TV, and free Wi-Fi, as well as a kitchen with a fridge, freezer, microwave, and oven. Guests can also enjoy fresh pastries for breakfast and take advantage of the nearby cycling opportunities.
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