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.
9.7 36 reviews
Pienza
27/06 – 28/06
NZ$410/nightfor 1 night
Fancy Garden
1 4
apartment , Montepulciano
This spacious Montepulciano apartment, sleeping up to six guests, is located a 0.24km walk from Porta al Prato and 0.12km from the Conad supermarket, offering easy access to the historic centre. The 100 sq m property features two double bedrooms, a living room with a sofa bed, two bathrooms, a fully equipped kitchen (including a dishwasher), free parking for three cars, and a jacuzzi.
10 31 reviews
Pienza
13/07 – 15/07
NZ$274/nighttotal: NZ$548 (2 )
Dimora Del Poggio Deluxe Apartment, Cozy & Elegant
1 2
apartment , San Quirico d'Orcia
This San Quirico d'Orcia apartment, ideally located near the Horti Leonini and Collegiate Church, offers easy walking access to the town's key attractions. The self-catering flat comprises one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher; air conditioning and parking are also provided.
9.7 467 reviews
Pienza
19/08 – 22/08
NZ$493/nighttotal: NZ$1479 (3 )
Agriturismo Riposati
2 4
house , Pienza
This house is located near Monticchiello, a charming village just 2 kilometres away, and a short 20-minute drive from the famous town of Montepulciano. It has received excellent ratings for location, cleanliness and user experience. The house has one bathroom and features a fully equipped kitchen, a garden and free Wi-Fi. Guests can enjoy stunning views of the Val d'Orcia hills and relax in the tranquil garden setting.
9.2 16 reviews
Pienza
09/07 – 10/07
NZ$170/nightfor 1 night
Apartment In The Medieval Village
1 2
apartment , Torrita di Siena
This Montefollonico apartment, in the medieval village near Torrita di Siena, is conveniently located 15km from Bagno Vignoni and 15km from Montepulciano Terme. The 70 square metre dwelling boasts a one-bedroom layout, sleeping up to seven guests, and includes a fully equipped kitchen, free Wi-Fi, and a shared lounge; a mini-market is also on-site.
9.3 175 reviews
Pienza
08/07 – 12/07
NZ$162/nighttotal: NZ$648 (4 )
Agriturismo I Capraccioni Monticchiello - Pienza
1 2
gîte , Pienza
This self-catering apartment, situated in the Val d'Orcia countryside, is 4km from Montepulciano and 2.5km from Monticchiello, offering easy access to these historic Tuscan towns. The 80 sq m ground-floor property sleeps two, features a private garden with children's play area and barbecue, and includes a kitchen, bathroom, and on-site parking.
9.5 12 reviews
Pienza
13/08 – 17/08
NZ$624/nighttotal: NZ$2496 (4 )
Renaissance House
1 6
house , Pienza
This three-bedroom, three-bathroom house in Pienza's pedestrian zone is situated near the Duomo and Piazza Pio II, offering easy access to shops and restaurants. Sleeping up to six guests, the property features a fully equipped kitchen, laundry facilities, and two fireplaces, plus king-size beds in each bedroom.
8.9 1525 reviews
Pienza
02/07 – 03/07
NZ$326/nightfor 1 night
Residenza D'epoca La Rosa
1 2
apartment , Pienza
Residenza d'Epoca La Rosa is situated in the historic centre of Pienza, just 31 miles from Siena and 75 miles from Florence Airport. This apartment has excellent ratings for location, cleanliness, and user experience. The property is a self-catering apartment with a well-equipped kitchen and comfortable living spaces. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, sauna, and spa, plus a terrace or balcony for relaxing outdoors.
Pienza
27/06 – 04/07
NZ$317/nighttotal: NZ$2219 (7 )
Old Mansion In The Village
1 2
apartment , San Quirico d'Orcia
This one-bedroom flat in San Quirico d'Orcia offers a prime location, situated a short walk from Horti Leonini and Palazzo Chigi, and a 13-minute drive from the Historic Centre of Pienza and Val di Chiana. This accommodation for two guests provides essential amenities including WiFi and heating, with towels, bed linen, soap, toilet paper, and a hairdryer supplied for your convenience.
Pienza
07/09 – 18/09
NZ$274/nighttotal: NZ$3014 (11 )
60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Pienza
This Pienza flat, situated in the Val d'Orcia, offers direct views of the UNESCO-listed medieval village and is 17 kilometres from Montepulciano's thermal baths. This 45 square metre flat accommodates up to four guests, featuring one bedroom, one bathroom, free Wi-Fi, and a fully equipped kitchen, providing an authentic Tuscan experience with easy access to nearby attractions.
9.2 37 reviews
Pienza
13/07 – 15/07
NZ$179/nighttotal: NZ$358 (2 )
Foresteria Del Teatro Povero
2 2
apartment , Pienza
This charming holiday home, Foresteria del Teatro Povero, is located in the tranquil village of Monticchiello, just a short drive from the popular tourist destination of Pienza, offering easy access to the surrounding Tuscan countryside. The apartment consistently receives excellent reviews for its cleanliness, location, and overall user experience. The two-bedroom apartment offers 63 square metres of space and comfortably accommodates up to three guests. This family-friendly property includes a fully equipped kitchen, a cosy living room with a fireplace, a restaurant on-site, and a tour desk for exploring the region.
10 1 review
Pienza
13/07 – 15/07
NZ$179/nighttotal: NZ$358 (2 )
46 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests
1 2
farm , Pienza
Farm listing for 2 people with an excellent rating of 100% based on 1 reviews. This accommodation is located in Pienza. Services and facilities include a barbecue, a garden and a fridge.
Best family friendly Pienza holiday rentals
Among the 69 accommodations in Pienza, here are the 4 best family friendly rentals
10 3 reviews
Pienza
23/10 – 24/10
NZ$608/nightfor 1 night
Il Podere Di Casa Rossa Pienza
4 2
apartment , Pienza
This family-friendly Pienza apartment, located within a 10-minute walk (less than 1 km) of the Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile, offers easy access to major historical sites. Sleeping eight guests in four bedrooms and three bathrooms, the property includes a fully equipped kitchen with dishwasher, a private garden, parking, and in-unit laundry facilities; housekeeping is available on request.
8.6 67 reviews
Pienza
04/07 – 12/07
NZ$228/nighttotal: NZ$1824 (8 )
Agriturismo Sant'agostino
1 2
farm , Montalcino
Agriturismo Sant'Agostino, a renovated farmhouse near San Giovanni d'Asso, is situated approximately 42km from Siena's Piazza del Campo and 22km from Bagno Vignoni, offering easy access to the Val d'Orcia and its renowned wineries. This self-catering property features a swimming pool, a terrace, a garden, free Wi-Fi, and private parking; selected rooms include kitchens with dishwashers, and all rooms are air-conditioned.
10 1 review
Pienza
16/08 – 19/08
NZ$18206/nighttotal: NZ$54618 (3 )
Villa ∙ 12 Bedrooms ∙ 24 Guests
12 13
house , Montepulciano
Villa Cicolina, near Montepulciano in the Tuscan countryside, offers a luxurious stay within easy reach of the town's attractions. This 18th-century villa and its two annexes provide spacious accommodation for up to 24 guests across 12 bedrooms and 11 bathrooms, boasting a private pool with hydromassage, a professional kitchen, and three self-contained apartments with kitchenettes and fireplaces.
9.7 47 reviews
Pienza
29/08 – 02/09
NZ$293/nighttotal: NZ$1172 (4 )
56 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests
1 2
farm , Pienza
Farm for up to 2 guests with an excellent rating of 97% based on 47 reviews. You will be based in Pienza. Services and facilities: a terrace, a freeze and a dish washer. Enjoy free parking with this accommodation in Pienza!
Best Pienza holiday rentals with parking
9.7 252 reviews
Pienza
02/08 – 05/08
NZ$247/nighttotal: NZ$741 (3 )
Ermione
1 1
apartment , Castiglione d'Orcia
This charming one-bedroom cottage is situated just half a mile from the historic Fortress of Tentennano in Castiglione d'Orcia, a picturesque town in the heart of Tuscany. It has received excellent ratings for location, cleanliness, and overall user experience. The cottage comfortably sleeps four guests and features a fully equipped kitchen, a cosy fireplace, and a washing machine. Guests can enjoy the private garden, relax on the sofa bed, and benefit from the convenient parking space.
8.0 49 reviews
Pienza
21/07 – 22/07
NZ$276/nightfor 1 night
Casa Di Isma
1 2
apartment , San Quirico d'Orcia
Casa di Isma is a family-friendly apartment in San Quirico d'Orcia, conveniently located 6km from Bagno Vignoni and 40km from Siena's Piazza del Campo, offering easy access to Mount Amiata. This 63 square metre flat features one bedroom, one bathroom, and sleeps nine guests, boasting a terrace, parking, Wi-Fi, and a kitchen with a fridge; an Italian breakfast and full-day security are optional extras.
9.0 103 reviews
Pienza
27/06 – 04/07
NZ$465/nighttotal: NZ$3255 (7 )
Sunflower
2 2
apartment , San Quirico d'Orcia
The Sunflower apartment is situated in San Quirico d'Orcia, a village in Tuscany, 40 kilometres from Mount Amiata and 45 kilometres from Siena's Piazza del Campo. This 90 square metre self-catering property has two bedrooms, a living room, a fully equipped kitchen and a private garden and terrace, perfect for enjoying the Tuscan sunshine.
9.8 76 reviews
Pienza
13/09 – 16/09
NZ$314/nighttotal: NZ$942 (3 )
La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany
2 2
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.
Frequently asked questions about holiday rentals in Pienza
What are some interesting places to visit in or near Pienza?
Pienza is a beautiful town to explore, with its charming cobbled streets and stunning views. You can visit the Duomo, a magnificent cathedral built in the 15th century, or the Palazzo Piccolomini, a grand Renaissance palace. For a scenic drive, head to the nearby Val d'Orcia, a stunning landscape dotted with rolling hills, vineyards, and cypress trees.
What are the best Airbnb and holiday rentals in Pienza?
Which walking or cycling routes are the best in Pienza?
The best walking route is the 'Sentiero della Bonifica', a scenic trail that follows the old irrigation canals and offers stunning views of the Val d'Orcia. For cycling, the 'Strada del Vino Nobile di Montepulciano' is a popular route that winds through vineyards and offers picturesque views of the surrounding countryside.
What other towns or cities can be easily accessed from Pienza?
You can easily visit nearby towns like Montepulciano, a charming town known for its wine production, and Montalcino, another beautiful hilltop town famous for its Brunello di Montalcino wine. Siena, a larger city with a historic centre, is also within easy reach.
What are the best holiday rentals with a pool in Pienza?
What amenities are commonly available in vacation rentals in Pienza?
Vacation rentals in Pienza typically offer basic amenities like a kitchen, bathroom, and bedrooms. Many also have a private garden or terrace, and some even have a swimming pool. You can find rentals with a range of amenities to suit your needs and budget.
What are the best rentals for families and kids in Pienza?
What time of year is best to rent a vacation rental Pienza?
Pienza is beautiful year-round, but the best time to visit is during 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.
What are the best rentals or Airbnbs with a jacuzzi in Pienza?
The region is famous for its pecorino cheese, made from sheep's milk. Be sure to try the 'Pecorino di Pienza', a local variety of pecorino cheese that is particularly creamy and delicious. Other local specialities include 'Pici cacio e pepe', a pasta dish made with pecorino cheese and black pepper, and 'Ribollita', a hearty Tuscan bread soup.
Destinations nearby
Best Pienza holiday rentals with a balcony
Pienza
27/06 – 28/06
NZ$680/nightfor 1 night
Premium Apartment - Helichrysum
2 4
apartment , Montepulciano
This Montepulciano apartment, near the Civic Museum and Adelina Quadri Art Studio, offers easy access to attractions such as La Foce and RI Crea RE. The 100-square-metre dwelling boasts two bedrooms, two bathrooms, a fully equipped kitchen (including a fridge and dishwasher), air conditioning, a terrace, and sleeps up to six guests.
This luxurious Montalcino castle enjoys a convenient location just steps from the Val di Chiana valley, 3.6km from the Saints Peter and Andrew Church, and within 10km of the Sant'Anna in Camprena Monastery and San Giovanni d'Asso railway station. This 4-bedroom, 4-bathroom property sleeps 8 guests and boasts a Jacuzzi, sauna, garden, terrace, and fully equipped kitchen including a dishwasher; barbecue facilities are also available for al fresco dining.
9.3 131 reviews
Pienza
27/06 – 28/06
NZ$1914/nightfor 1 night
Poggio Paradiso Resort & Spa
2 4
resort , Torrita di Siena
Poggio Paradiso Resort & Spa is located in Montefollonico, a charming village just 18 kilometres from Montepulciano Terme and 50 kilometres from Piazza Grande. The resort has consistently received excellent ratings from guests for its location, cleanliness, and overall experience. The resort offers a range of comfortable rooms with private bathrooms and some featuring balconies. Guests can enjoy a variety of amenities, including a swimming pool, a spa, a restaurant, and a bar, as well as activities like cycling and exploring the surrounding Tuscan countryside.
9.6 340 reviews
Pienza
17/08 – 19/08
NZ$1074/nighttotal: NZ$2148 (2 )
Monastero Sant'anna In Camprena
2 4
farm , Pienza
Fattoria Monastero Sant'Anna in Camprena is located in the Tuscan countryside, just 19 kilometres from Bagno Vignoni and 23 kilometres from Montepulciano Terme, offering a peaceful escape from the hustle and bustle of Pienza. This farm stay has consistently received excellent ratings for its location, cleanliness and overall guest experience. The property features a charming restaurant, a garden and a terrace, providing ample space for relaxing and enjoying the beautiful surroundings. This farm stay can accommodate up to two guests in its comfortable and modern accommodation, which includes air conditioning, a private bathroom, a fridge, a microwave oven and free Wi-Fi.
Best pet friendly Pienza holiday rentals
Among the 69 accommodations in Pienza, here are the 4 best pet friendly rentals
9.8 23 reviews
Pienza
13/07 – 17/07
NZ$732/nighttotal: NZ$2928 (4 )
110 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests
3 2
farm , Pienza
Farm for up to 7 people with an excellent rating of 98% based on 23 reviews. You will be based in Pienza. Services and facilities: a washing machine, a fridge and a freeze. Take advantage of the terrace in this accommodation!
9.0 343 reviews
Pienza
13/09 – 16/09
NZ$302/nighttotal: NZ$906 (3 )
Casa Della Fonte
2 2
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.
8.9 218 reviews
Pienza
28/07 – 31/07
NZ$644/nighttotal: NZ$1932 (3 )
Agriturismo Podere Casella
3 5
farm , Castiglione d'Orcia
Agriturismo Podere Casella is situated in Castiglione d'Orcia, a mere 6.1 kilometres from the famous thermal baths of Bagno Vignoni. This one-bedroom farmhouse offers comfortable accommodation for up to three guests, with a private garden, free Wi-Fi, and parking, perfect for a peaceful rural escape.
9.2 21 reviews
Pienza
27/06 – 04/07
NZ$396/nighttotal: NZ$2772 (7 )
L' Antica Oliviera D'orcia
2 2
apartment , San Quirico d'Orcia
This two-bedroom apartment in L'Antica Oliviera D'Orcia is conveniently located in San Quirico d'Orcia, just 5.8 kilometres from the thermal baths of Bagno Vignoni and 22.5 kilometres from Bagni San Filippo. The 75 square metre property offers a modern kitchen with a fridge, microwave oven, and dishwasher, as well as a terrace, garden, and barbecue facilities, accommodating up to seven guests.