Holiday Rentals in Pienza

114 available vacation rental offers

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Pienza holiday rentals
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Best Holiday rentals and Airbnb offers in Pienza

Best family friendly Pienza holiday rentals

Among the 114 accommodations in Pienza, here are the 4 best family friendly rentals

Il Casone - Pienza
9.4 81 reviews

Il Casone

apartment, Montalcino
This two-bedroom apartment is situated in Montisi, a peaceful village just 15 miles from Bagno Vignoni and 16 miles from Montepulciano Terme, offering a tranquil escape from the bustling crowds of Montalcino. The property has received excellent ratings for cleanliness, location and overall user experience.
The self-catering apartment is spread over 130 square metres and features a fully equipped kitchen with a dishwasher, a comfortable living area, and a private bathroom. Guests can enjoy free Wi-Fi, parking, and a private entrance, as well as bed linen and towels.
Appartamenti Il Leone - Pienza
8.0 182 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.
Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo! - Pienza
10 47 reviews

Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo!

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.
Val D'orcia Nel Borgo - Pienza
9.2 167 reviews

Val D'orcia Nel Borgo

apartment, Castiglione d'Orcia
This three-bedroom apartment is situated in Castiglione d'Orcia, just a short drive from the famous thermal baths of Bagno Vignoni and within easy reach of other attractions like Bagni San Filippo and Montepulciano Terme. The property has received excellent ratings for its location, cleanliness and overall experience.
The spacious apartment, covering 85 square metres, comfortably accommodates up to eight guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, Wi-Fi and parking, as well as access to a tennis court and nearby skiing opportunities.

Best Pienza holiday rentals with parking

Villa Pesca Amazing House In The Heart Of Tuscany - Pienza
No reviews

Villa Pesca Amazing House In The Heart Of Tuscany

apartment, Trequanda
This spacious villa is located within Cignella Resort in Trequanda, offering Tuscan views and convenient access to local cultural sites such as the Artemisia Gallery and Palazzo Borgia, with shopping at Valdichiana Outlet Village approximately 15 kilometers away.
This 156 square meter villa accommodates up to 6 guests with 3 bedrooms, a large open-plan living area, a fully equipped kitchen, and a private garden or terrace, alongside complimentary Wi-Fi and resort parking, plus access to shared resort amenities.
Agriturismo Bagnolo - Pienza
8.9 234 reviews

Agriturismo Bagnolo

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.
Panoramic Apaertment Val D'orcia - Pienza
9.7 172 reviews

Panoramic Apaertment Val D'orcia

apartment, Pienza
This B&B is located in the historic centre of Pienza, just a 10-minute drive from the thermal baths of Bagno Vignoni and the picturesque town of Montepulciano.
The studio apartment features a fresco depicting a temple and architectural motifs, a private bathroom, and secure motorcycle parking.
Agriturismo Selvoli - Il Bruco - Pienza
9.9 24 reviews

Agriturismo Selvoli - Il Bruco

gîte, Pienza
This self-catering apartment, part of a renovated farmhouse in the Val d'Orcia, is located 5km from both Pienza and Bagno Vignoni.
The two-bedroom, two-bathroom property sleeps four, features a well-equipped kitchen with a microwave and fridge, offers private outdoor space with a barbecue, and includes access to a shared swimming pool (June-September).

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town, so you'll want to explore its historic centre, especially Piazza Pio II, with its stunning cathedral. You can also visit the nearby town of Montepulciano, known for its wine production and beautiful Renaissance architecture.
  • 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 is a great area for cycling, so you could try the 40km route from Pienza to San Quirico d'Orcia. For a shorter walk, you can take the 1.5km trail from Pienza to the Corsignano Fortress, which offers fantastic views of the valley.
  • 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 other towns or cities can be easily accessed from Pienza?

    You can easily reach Siena by car in about 45 minutes, or by bus. The charming town of Montalcino is also within easy reach, about 30 minutes away by car. Florence is about 1 hour and 45 minutes away by car.
  • 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 amenities are commonly available in vacation rentals in Pienza?

    Most vacation rentals in Pienza will have a kitchen, a bathroom, and a living area. Many also have a private garden or terrace, and some may have a swimming pool. You'll usually find Wi-Fi and air conditioning, too.
  • 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 time of year is best to rent a vacation rental Pienza?

    The best time to visit Pienza is during the shoulder seasons, from April to May or September to October, when the weather is mild and the crowds are smaller. You can also enjoy the summer months, from June to August, but it can get quite hot and busy.
  • 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.

Popular destinations

Best Pienza holiday rentals with a balcony

70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
10 6 reviews

70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Pienza
Agriturismo Il Casato - Il Torchio, a self-catering apartment, is situated 1 kilometre from Pienza's historic centre, offering breathtaking views of the Val d'Orcia and easy access to attractions such as the Vitaleta Chapel (7km), Montepulciano (15km), and Siena (50km).
This 70 square metre property sleeps four, featuring a living room, well-equipped kitchen, one bedroom, one bathroom, and access to a private barbecue area, plus shared garden and terrace; amenities include Wi-Fi, air conditioning, and a washing machine, with optional homemade breakfast and guided winery tours available.
42 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests - Pienza
No reviews

42 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Castiglione d'Orcia
Il Giogo apartment in Castiglione d’Orcia offers a convenient base for exploring Tuscany, being within easy reach of the town's amenities and attractions.
This 42 square metre self-catering property features two bedrooms, two bathrooms, a private terrace, and access to a shared swimming pool, garden, and barbecue area, comfortably sleeping six adults and a baby.
Agriturismo Sant'agostino - Pienza
8.7 70 reviews

Agriturismo Sant'agostino

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.
La Casa Di Manu - Pienza
9.3 18 reviews

La Casa Di Manu

apartment, Montepulciano
La Casa di Manu is a self-catering apartment in Abbadia di Montepulciano, conveniently located 9.6km from Piazza Grande in Montepulciano and 14km from the Terme di Montepulciano.
This 80 square metre property features one bedroom, one bathroom, and can accommodate three guests, boasting a fully equipped kitchen, private parking, a terrace, garden, and outdoor play equipment.

Best pet friendly Pienza holiday rentals

Among the 114 accommodations in Pienza, here are the 4 best pet friendly rentals

Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
8.0 1 review

Villa Basilico - Cignella Resort Chalet In Tuscany

chalet, Trequanda
This Trequanda holiday home is located in Osteria Delle Noci, 46 kilometres from Piazza Grande and 17 kilometres from Montepulciano Terme.
This two-bedroom, two-bathroom chalet offers 93 square metres of living space for up to seven guests, featuring air conditioning, a dishwasher, a microwave, and access to a communal swimming pool at Villa Basilico - Cignella Resort.
Agriturismo Il Macchione - Pienza
9.3 590 reviews

Agriturismo Il Macchione

house, Pienza
This 18th-century farmhouse is located just 0.9 miles outside of Pienza, overlooking the stunning Val d'Orcia Natural Park, offering a secluded and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse features a spacious terrace with a swimming pool and hydromassage area, perfect for relaxing and enjoying the beautiful surroundings. Guests can also enjoy a range of amenities, including a fitness center, tennis court, and a children's playground, as well as a buffet breakfast and BBQ facilities.
Villa Gallina Grande Stay - Pienza
9.4 76 reviews

Villa Gallina Grande Stay

house, Castiglione d'Orcia
Sant'Alberto farmhouse, in Campiglia d'Orcia, enjoys a peaceful countryside setting, 8km from Bagni San Filippo and 10km from Bagno Vignoni, offering easy access to the thermal baths and the nearby town of Montepulciano Terme (23km).
This pet-friendly property boasts a swimming pool, tennis court, and barbecue facilities, alongside Wi-Fi, a fully equipped kitchen, and ample parking; table tennis and children's play equipment are also available.
Le Sorbelle D'orcia - Pienza
9.5 152 reviews

Le Sorbelle D'orcia

farm, Pienza
Agriturismo Le Sorbelle d'Orcia, near Pienza in Tuscany, is conveniently located 19 kilometres from Montepulciano Terme, 21 kilometres from Bagni San Filippo, and 4.3 kilometres from Bagno Vignoni, offering easy access to these popular towns.
This one-bedroom, one-bathroom rural retreat sleeps three guests and boasts a swimming pool, free private parking, and a varied breakfast; bachelor/hen parties are not permitted.
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