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.

Villa Cielo- Cignella Resort Tuscany Accommodation - Pienza
No reviews

Villa Cielo- Cignella Resort Tuscany Accommodation

house, Trequanda
This spacious 160 square meter villa, located in Trequanda, offers panoramic views of the Tuscan hills and is situated within the Cignella Resort, providing convenient access to local attractions such as the Artemisia Gallery and Palazzo Borgia. This family-friendly property accommodates up to six guests across three bedrooms, features a fully equipped kitchen with a dishwasher and washing machine, air conditioning, Wi-Fi, and access to resort common areas including a swimming pool and gardens, with parking available.
Podere Pratovecchio 14&2, Emma Villas - Pienza
8.9 3 reviews

Podere Pratovecchio 14&2, Emma Villas

house, Torrita di Siena
This spacious 8-bedroom villa, located in Montefollonico near Montepulciano Terme, is 14 kilometres from Montepulciano Terme and within easy driving distance of Bagno Vignoni (26 km) and Bagni San Filippo (39 km), offering easy access to Tuscany's thermal baths.
The 600 square metre property boasts a private pool, extensive garden, barbecue facilities, free Wi-Fi, and parking, comfortably accommodating large families or groups with its eight bedrooms and eight bathrooms.
195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests - Pienza
10 8 reviews

195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Pienza
This spacious 195 square metre holiday home is situated in Monticchiello, a medieval village in the Val d'Orcia, a UNESCO World Heritage site, a short drive from Pienza and offering proximity to the unique 'poor theatre' tradition.
The three-bedroom, two-bathroom property boasts a fireplace, terrace, garden, parking, and features including a dishwasher and air conditioning, comfortably sleeping eight guests and providing easy access to Lake Trasimeno and other Tuscan attractions.
Chalet Cigno - Apartment In Tuscany - Pienza
No reviews

Chalet Cigno - Apartment In Tuscany

chalet, Trequanda
Chalet Cigno, a detached holiday home in Trequanda, offers convenient access to shopping at Valdichiana Outlet Village and Piazza Italia, and is within easy reach of the Historic Centre of Pienza and Val di Chiana, all within a 15 kilometre radius.
This 70 square metre, two-bedroom cottage accommodates up to three guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, private garden, and access to resort common areas including a swimming pool, with underfloor heating ensuring comfort throughout the year.

Best Pienza holiday rentals with parking

Mooi Appartement+terrassen+a/c In 13e Eeuws Stadje - Pienza
9.2 69 reviews

Mooi Appartement+terrassen+a/c In 13e Eeuws Stadje

apartment, Torrita di Siena
This apartment is situated in the medieval village of Montefollonico, a charming location just 10km from Torrita di Siena, and within easy reach of Pienza and Montepulciano. The property has received excellent user and location ratings, and a very good cleanliness rating.
This two-bedroom, one-bathroom property sleeps up to four guests and is ideal for families or groups of friends. The apartment includes a well-equipped kitchen, a private garden, a jacuzzi, a swimming pool just 10km away, and a wood-burning fireplace for cosy evenings.
Sunflower - Pienza
8.8 96 reviews

Sunflower

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.
Stile Toscano, Valdorcia - Pienza
9.0 16 reviews

Stile Toscano, Valdorcia

apartment, Torrita di Siena
This one-bedroom apartment in Torrita di Siena's historic centre offers stunning panoramic views of the Val d'Orcia, with local amenities such as restaurants and a grocery store within easy walking distance.
The self-catering flat sleeps two guests and features a fully equipped kitchen (including a fridge, freezer and dishwasher), air conditioning, private garden, parking and very good user ratings.
Casa Costanza - Pienza
9.4 48 reviews

Casa Costanza

house, Castiglione d'Orcia
Casa Costanza is located in Castiglione d'Orcia, a short drive from the renowned thermal baths of Bagno Vignoni and the picturesque village of Bagni San Filippo. The property has excellent user, location and cleanliness ratings.
The two-bedroom, two-bathroom property spans 68 square metres. Guests can enjoy stunning views, a shared lounge, an outdoor fireplace, a fully equipped kitchen, a flat-screen TV, complimentary Wi-Fi, bathrobes, towels and bed linen.

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.

Villa Petroio - Luxury Home With Private Pool - Pienza
No reviews

Villa Petroio - Luxury Home With Private Pool

house, Trequanda
This large villa in Rome offers convenient access to public transport, with Anagnina Metro Station 4.5 kilometres away and Porta Maggiore 6.4 kilometres away, placing it within reach of the Archbasilica of Saint John Lateran.
This 450 square metre house accommodates up to 27 guests across seven bedrooms and seven bathrooms, featuring a private swimming pool, free Wi-Fi, and private parking.
Villa In Montepulciano With 7 Bedrooms Sleeps 14 - Pienza
No reviews

Villa In Montepulciano With 7 Bedrooms Sleeps 14

house, Montepulciano
This seven-bedroom villa is situated in Montepulciano, Tuscany, within 2km of the Val di Chiana and Triacca Winery, and 5km from San Biagio and the Torre del Pulcinella.
This 650 square metre property boasts seven bedrooms and bathrooms, accommodating up to 14 guests, and features a private swimming pool, Jacuzzi, spa, and extensive gardens with barbecue facilities; free Wi-Fi is also available.
Casina Belvedere - Pienza
9.3 10 reviews

Casina Belvedere

apartment, San Quirico d'Orcia
Casina Belvedere, situated in San Quirico d’Orcia, is a short 5.3km drive from Bagno Vignoni and offers easy access to other Tuscan towns like Montepulciano Terme (24km).
This 68 square metre apartment features one bedroom, two bathrooms, and sleeps seven, boasting a fully equipped kitchen, private balcony, free Wi-Fi, and on-site parking.
Agriturismo Marinello - Pienza
9.4 612 reviews

Agriturismo Marinello

farm, Pienza
Agriturismo Marinello is located in the Val d’Orcia, a UNESCO World Heritage Site, just 4km from the centre of Pienza and a 32km drive from Montalcino. The farm has received excellent ratings for location, cleanliness and overall experience.
The farm offers both rooms and apartments, all with traditional Tuscan features, like wood-beamed ceilings and wrought-iron beds. Guests can enjoy a private garden, a swimming pool open from May to September, and a fully equipped kitchen.

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.

Elegant Chalet On The Ground Floor Of Approximately 80 M2 Consisting Of A Large Living Room With Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.a Double Bedroom And A Single Bedroom, - Pienza
No reviews

Elegant Chalet On The Ground Floor Of Approximately 80 M2 Consisting Of A Large Living Room With Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.a Double Bedroom And A Single Bedroom,

chalet, Trequanda
This Trequanda holiday home is conveniently located a short 0.8 km walk from the Val di Chiana and a 24 km drive from Palazzo Piccolomini.
The 80 square metre property offers two bedrooms, one bathroom, and sleeps three guests, boasting a private garden, swimming pool, and modern amenities including Wi-Fi and air conditioning.
Lignanello Country House - Pienza
9.4 35 reviews

Lignanello Country House

apartment, Pienza
Lignanello Country House is situated in the countryside near Pienza, just 14 kilometres from Montepulciano Terme and 16 kilometres from Bagno Vignoni, offering a peaceful retreat away from the town. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This spacious three-bedroom apartment, spanning 120 square metres, comfortably accommodates up to six guests. Enjoy a fully equipped kitchen, a terrace with mountain views, a garden, a children's playground, and free parking and Wi-Fi.
Casa X2 Con Veranda In Mascagni Farmhouse Pienza - Pienza
No reviews

Casa X2 Con Veranda In Mascagni Farmhouse Pienza

house, Pienza
This restored 16th-century olive oil mill, offering an authentic Renaissance apartment, is situated within the Mascagni Organic Farm, providing immersive Tuscan countryside experiences with unobstructed views of the Val d'Orcia.
This property features 1 bedroom and 1 bathroom, accommodating up to 2 guests, and includes a private veranda, air conditioning, a kitchen with a fridge, freezer, and microwave, as well as a garden and parking.
50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.4 21 reviews

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Castiglione d'Orcia
Farm for 5 people with an excellent rating of 94% based on 21 reviews. Your accommodation will be located in Castiglione d'Orcia.
Facilities and services: event friendly rooms, a kitchen and a jacuzzi. This accommodation in Castiglione d'Orcia has a swimming pool!
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