Holiday Rentals in Pienza

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Pienza holiday rentals
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114 Holiday rentals and Airbnb in Pienza

Best family friendly Pienza holiday rentals

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

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.5 64 reviews

Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Pienza
Farm for 5 guests with an excellent rating of 95% based on 64 reviews. You will be located in Pienza.
Services and facilities include a swimming pool, a garden and a fridge. This is a pet-friendly accommodation!
Samsara Apartment - Pienza
10 9 reviews

Samsara Apartment

apartment, Pienza
Samsara Apartment is a family-friendly flat located in Pienza, a UNESCO World Heritage site, approximately 16km from Montepulciano Terme and Bagno Vignoni, and 26km from Bagni San Filippo.
This 65 square metre, two-bedroom property sleeps up to nine guests and features a fully equipped kitchen with a dishwasher, microwave, and fridge, plus air conditioning and free Wi-Fi.
46 M² Apartment ∙ 1 Bedroom ∙ 3 Guests - Pienza
No reviews

46 M² Apartment ∙ 1 Bedroom ∙ 3 Guests

apartment, Torrita di Siena
This apartment is located within the Tiberini Estate in Torrita di Siena, part of the wider Tiberini Estate in Montepulciano, offering views of the Valdichiana and Val d'Orcia regions.
This 46 square meter holiday home sleeps up to four guests, featuring one bedroom, one bathroom, a kitchen with a fridge, freezer, and dishwasher, and access to shared amenities including a swimming pool, garden, and playground, with high-speed WiFi and breakfast included.
Il Podere Di Casa Rossa Pienza - Pienza
10 3 reviews

Il Podere Di Casa Rossa Pienza

farm, 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.

Best Pienza holiday rentals with parking

Agriturismo Riposati - Pienza
9.6 259 reviews

Agriturismo Riposati

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.
Podere Le Mulina - Pienza
8.6 82 reviews

Podere Le Mulina

farm, Castiglione d'Orcia
Podere le Mulina is a farm stay located in Castiglione d'Orcia, just 5.5 kilometres from Bagno Vignoni and 35 kilometres from Mount Amiata, offering a peaceful escape in the Tuscan countryside. It has received very good ratings for its cleanliness and overall user experience, with a good location rating.
The farm stay features a fully equipped kitchen with a fridge, oven, and stovetop, allowing guests to prepare their own meals. Guests can enjoy the outdoor amenities, including a swimming pool, a garden, and a picnic area, perfect for relaxing and enjoying the Tuscan sunshine.
Appartamento Antica Toscana - Pienza
9.8 147 reviews

Appartamento Antica Toscana

apartment, Pienza
This charming apartment is situated in the historic centre of Pienza, just a stone's throw from the Piazza del Duomo and the Duomo itself, offering a peaceful escape in the heart of this beautiful Tuscan town. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is perfect for a family of four, with two bedrooms and two bathrooms. It is equipped with a kitchen featuring a fridge and dishwasher, as well as free internet access and parking. Guests can enjoy stunning views of the surrounding countryside from the apartment, and explore the town's charming streets and shops, all within easy reach.
Casa Refenero - Pienza
9.3 43 reviews

Casa Refenero

apartment, Torrita di Siena
CASA REFENERO, a family-friendly apartment in Torrita di Siena, is conveniently located 16km from Montepulciano Terme and within easy driving distance of other Tuscan attractions including Piazza Grande (45km), Bagno Vignoni (31km), and Bagni San Filippo (43km).
This 90 square metre dwelling boasts two bedrooms, two bathrooms, and sleeps up to nine guests, offering free Wi-Fi, private parking, a terrace, a fully equipped kitchen with dishwasher, and packed lunches for day trips.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town with plenty to see. You should definitely visit the Duomo, a stunning example of Renaissance architecture, and the Palazzo Piccolomini, a magnificent palace with a beautiful courtyard. For a stunning view of the Val d'Orcia, head to the Fortezza, a medieval fortress on a hill overlooking the town. If you want to explore the surrounding area, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia, all of which are within a 30-minute drive.
  • 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?

    For walking, you can take a stroll around the historic centre, visiting the main sights. There's also a lovely walk along the Via Cassia, an ancient Roman road that runs through the Val d'Orcia. For cycling, the Val d'Orcia is a great place to explore, with rolling hills and stunning views. You can follow the Via Cassia or head out to the nearby town of Montepulciano for a longer ride.
  • 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 place for outdoor activities. You can go hiking in the surrounding hills, go for a swim in the nearby Lake Trasimeno, or play tennis at the local tennis club. There are also several horse riding schools in the area, so you can enjoy a horseback riding tour of the Val d'Orcia.
  • 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. If you're looking for a day trip, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia.
  • 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?

    Vacation rentals in Pienza typically come with a range of amenities. Most rentals have a kitchen, a bathroom, and a living area. Many also have a private garden or terrace, and some even have a swimming pool. You can find rentals that are perfect for families, couples, or groups of friends.
  • 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?

    The best time to visit Pienza is during the spring or autumn, when the weather is mild and the crowds are smaller. The summer months can be very hot and crowded, but if you don't mind the heat, you can enjoy the many outdoor activities that Pienza has to offer.

Popular destinations

Best Pienza holiday rentals with a balcony

Casa Remolina - Pienza
9.7 40 reviews

Casa Remolina

house, Torrita di Siena
Casa Remolina, in Montefollonico, offers a peaceful retreat in the Tuscan countryside, situated approximately 16km from Montepulciano Terme and 24km from Bagno Vignoni.
This 110 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, private garden, terrace, free Wi-Fi and parking.
150 M² House ∙ 4 Bedrooms ∙ 8 Guests - Pienza
8.1 10 reviews

150 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, San Quirico d'Orcia
This Tuscan villa is situated near San Quirico d'Orcia, offering easy access to the town's attractions and the Church of Santa Maria Assunta's Renaissance garden.
The 150 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a kitchen with a fridge and dishwasher, plus a terrace, garden, parking, and internet access.
Villa Aquila-cignella Resort Acommodation  Tuscany - Pienza
No reviews

Villa Aquila-cignella Resort Acommodation Tuscany

house, Trequanda
This luxury apartment is situated in Trequanda, a short distance from landmarks such as Chiesa di San Francesco and Palazzo Piccolomini, and attractions including RI Crea RE and Art Studio di Adelina Quadri.
This 220 square meter residence accommodates up to six guests across three bedrooms and three bathrooms, featuring a double-height living room with exposed wooden beams, a fully equipped kitchen, complimentary Wi-Fi, resort parking, and access to the Cignella Resort's gardens and swimming pool.
Debby Appartamenti - Pienza
9.3 90 reviews

Debby Appartamenti

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.

Best pet friendly Pienza holiday rentals

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

L’ Angolo Di Pienza - Pienza
8.6 232 reviews

L’ Angolo Di Pienza

apartment, Pienza
L’ANGOLO DI PIENZA is located in the charming town of Pienza, just 45km from Mount Amiata, surrounded by the beautiful Val d’Orcia, a UNESCO World Heritage Site. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom flat offers a comfortable living space with a sofa, seating area, and a flat-screen TV. It also features a well-equipped kitchen, a private bathroom, and a swimming pool. Guests can enjoy the peace and quiet of Pienza, explore the nearby attractions, and relax in the beautiful surroundings.
Al Piccolo Ulivo, A Casa Di Mimo&sè - Pienza
9.5 25 reviews

Al Piccolo Ulivo, A Casa Di Mimo&sè

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.
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.
Villa Tiberini Wine Relais - Pienza
9.7 22 reviews

Villa Tiberini Wine Relais

farm, Torrita di Siena
Villa Tiberini Wine Relais, situated in Osteria Delle Noci, is 46 kilometres from Piazza Grande and 17 kilometres from the Terme di Montepulciano.
This farm stay offers satellite TV, a fully equipped kitchen, free Wi-Fi, private parking, an outdoor swimming pool, and a garden with barbecue facilities, with Montepulciano Thermal Baths a 17-kilometre drive away.
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