This Tuscan-style apartment, near Castiglione d’Orcia, is conveniently located a short distance from the Rocca di Castiglione and offers easy access to other historical towns along the Via Francigena. The two-bedroom, one-bathroom property sleeps four, features a private garden, free on-site parking, and a fully equipped kitchen including a dishwasher, and is ideal for exploring the local area's nature trails and wineries.
9.8 84 reviews
Pienza
06/27 – 06/28
HK$3334/nightfor 1 night
Donna Laura - Holiday Home
3 4
house , San Quirico d'Orcia
Donna Laura, a renovated 11th-century holiday home in San Quirico d'Orcia, Val d'Orcia, is situated 40km from Monte Amiata and 47km from Piazza del Campo in Siena. This pet-friendly property offers free Wi-Fi, private parking, air conditioning, and features such as a fully equipped kitchen (in select units), flat-screen TVs with streaming services, and private bathrooms with bidets; its proximity to San Quirico d'Orcia's attractions ensures a convenient stay.
9.0 235 reviews
Pienza
08/29 – 09/02
HK$1123/nighttotal: HK$4492 (4 )
Agriturismo Bagnolo
1 2
farm , Pienza
Agriturismo Bagnolo is a farm stay situated in the Tuscan countryside, just 4km from the historic town of Pienza, and within easy reach of Montepulciano and Chianciano Terme. This highly-rated property boasts excellent user, location, and cleanliness ratings. The farm offers a choice of rooms and apartments, accommodating up to two guests. Enjoy a range of amenities including a jacuzzi, terrace, garden, and parking, as well as the opportunity to participate in the production of oil and cheese, and witness the farm's animals firsthand.
9.2 74 reviews
Pienza
07/19 – 07/23
HK$1064/nighttotal: HK$4256 (4 )
Pienzalettings Studio & Room
1 2
studio , Pienza
PienzaLettings Studio & Room is a self-catering apartment in Pienza, conveniently located 16km from Montepulciano Terme, 16km from Bagno Vignoni, and 24km from Bagni San Filippo. This pet-friendly studio sleeps three, features a kitchen with a fridge and microwave, air conditioning, Wi-Fi, and a private bathroom with a bidet and hairdryer; Mount Amiata is a 45km drive away.
9.4 24 reviews
Pienza
08/18 – 08/22
HK$2120/nighttotal: HK$8480 (4 )
Agriturismo Il Casato Mag-il Vaglio
2 4
farm , Pienza
Agriturismo il casato mag-il vaglio is located in Pienza, just 43km from Mount Amiata, 9km from Bagno Vignoni, and 18km from Montepulciano Terme, making it a great base for exploring the beautiful Tuscan countryside. This farm stay has received excellent ratings for its location, cleanliness and overall experience. The property offers a 70 square metre apartment with two bedrooms, one bathroom, and a capacity for four guests. It has a fully equipped kitchen, air conditioning, a terrace, a garden, free Wi-Fi, parking, and a range of activities including table tennis and bike rentals.
Pienza
12/07 – 12/10
HK$3639/nighttotal: HK$10917 (3 )
Maria Gabriella Holiday Home
3 8
apartment , Pienza
This independent house and separate cottage are located in Monticchiello, a village within the Val d'Orcia region, offering direct access to its renowned landscapes and historic sites. Accommodating up to eight guests, this property features three bedrooms with en-suite bathrooms in the main house, plus an additional en-suite bedroom and kitchenette in the cottage, all equipped with air conditioning, internet, and on-site parking.
9.9 38 reviews
Pienza
08/17 – 08/19
HK$2365/nighttotal: HK$4730 (2 )
Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo!
1 4
apartment , Pienza
This charming flat is located in the heart of Pienza, just 50 metres from the Duomo and Palazzo Piccolomini, offering easy access to the town's main attractions and the bustling atmosphere of Corso Il Rossellino. The property has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers. The apartment has one bedroom and one bathroom and can comfortably accommodate up to three guests. The well-equipped kitchen features a fridge, freezer, and dishwasher, and the property also benefits from free internet access.
9.7 613 reviews
Pienza
08/16 – 08/19
HK$46887/nighttotal: HK$140661 (3 )
Mastrojanni Relais
6 13
farm , Montalcino
Mastrojanni Relais is a farm stay located in Castelnuovo dell’Abate, just 39 kilometres from both Siena and Saturnia, offering a peaceful rural setting near popular tourist destinations. The property has received excellent ratings for location, cleanliness and user experience. The accommodation features private bathrooms, flat-screen TVs and free Wi-Fi in each room, along with a range of amenities such as a swimming pool, a sauna, a spa, a restaurant, a bar and a fitness centre. Guests can also enjoy a terrace, a garden and room service.
10 2 reviews
Pienza
08/17 – 08/19
HK$2890/nighttotal: HK$5780 (2 )
Apartment "Agriturismo Il Casato Mag-il Vaglio" With Mountain View, Terrace And Wi-fi
2 4
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.
9.7 103 reviews
Pienza
07/08 – 07/12
HK$1318/nighttotal: HK$5272 (4 )
Pienza Romantica Valdorcia La Torre Di S.guglielmo
1 2
gîte , Pienza
This charming tower house is located just 600 metres from the historic walls of Pienza, in the heart of the stunning Val d'Orcia. This property has consistently received excellent ratings for location, cleanliness and user experience. The self-catering accommodation sleeps two guests and features a spacious garden with olive trees, perfect for relaxing and enjoying the Tuscan sunshine. Enjoy modern amenities like Wi-Fi, Netflix, and a coffee machine, as well as breakfast provisions and walking trails starting directly from the property.
10 1 review
Pienza
08/16 – 08/19
HK$13772/nighttotal: HK$41316 (3 )
Luxury 6br Val D'orcia Villa With Pool & Views
6 13
house , Sarteano
Villa Sambuco, a luxury Tuscan property near Sarteano, enjoys stunning 360° views of the Val d'Orcia, a UNESCO World Heritage site, and is situated between Sarteano and Radicofani in the Valdichiana and Val d'Orcia regions. This six-bedroom, seven-bathroom villa sleeps 13, boasts a heated infinity pool, private gym, extensive gardens, and features a fully equipped kitchen, including a dishwasher; guests can also enjoy fresh produce from the on-site vegetable garden, henhouse, and orchard.
9.4 26 reviews
Pienza
07/09 – 07/19
HK$1724/nighttotal: HK$17240 (10 )
Al Piccolo Ulivo, A Casa Di Mimo&sè
2 3
house , Castiglione d'Orcia
Al Piccolo Ulivo is located in Castiglione d'Orcia, just a short drive from the famous thermal baths of Bagno Vignoni and Mount Amiata, offering a peaceful retreat amidst the Tuscan countryside. This property consistently receives excellent ratings for its cleanliness, location, and overall user experience. The villa provides comfortable accommodation for up to four guests in two bedrooms, spanning 106 square metres. Enjoy a well-equipped kitchen, modern amenities, and a shared lounge, along with a private garden offering stunning views and access to outdoor activities like skiing, cycling, and hiking in the surrounding area.
Best family friendly Pienza holiday rentals
Among the 69 accommodations in Pienza, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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?
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 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?
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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.