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

In Toscana Camere - Pienza
9.8 161 reviews

In Toscana Camere

house, Pienza
In Toscana Camere, you'll find a peaceful countryside retreat located just 10km from Pienza, a 24km drive from Montepulciano, and 48km from Montalcino. The property has received excellent ratings for cleanliness, location, and user experience.
The houses and apartments offer a blend of traditional Tuscan charm and modern amenities. Guests can enjoy a fully equipped kitchen, free Wi-Fi, air conditioning, and a garden, perfect for relaxing and enjoying the peaceful surroundings.
Apartment Montello 1 - Pienza
9.9 70 reviews

Apartment Montello 1

apartment, Pienza
This Pienza apartment, near Monticchiello (2km from Pienza), boasts breathtaking Val d'Orcia views and is conveniently located for exploring the region.
The self-catering flat offers one bedroom, one bathroom, sleeps two, includes a fully equipped kitchen with a barbecue, a panoramic terrace, private parking, and free Wi-Fi, plus complimentary Italian breakfast provisions.
Dimora Delle Mura - Pienza
9.6 136 reviews

Dimora Delle Mura

apartment, San Quirico d'Orcia
Dimora delle Mura is a two-bedroom apartment situated in San Quirico d'Orcia, just 40km from Mount Amiata and 45km from Piazza del Campo in Siena. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment, spanning 65 square metres, comfortably accommodates up to seven guests. It features a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and a private check-in/check-out process.
La Tresa Country Living - Pienza
9.5 22 reviews

La Tresa Country Living

farm, Montepulciano
La Tresa Country Living is a farm stay located in Montepulciano, offering garden views and convenient access to local attractions.
This pet-friendly, family-friendly accommodation features one bedroom and one bathroom, with complimentary WiFi, private parking, a garden, a terrace, and an outdoor picnic area.

Best Pienza holiday rentals with parking

Il Giardino Del Cardinale - Deb's Monticchiello - Pienza
10 90 reviews

Il Giardino Del Cardinale - Deb's Monticchiello

house, Pienza
Il Giardino del Cardinale, a spacious villa in Monticchiello, is situated 10.5 km from Montepulciano and 13.2 km from Bagno Vignoni, offering easy access to renowned Tuscan wineries and thermal springs.
This 350 square metre property boasts three bedrooms, four bathrooms, two living rooms, a private garden, terrace, on-site restaurant and free Wi-Fi, comfortably accommodating families or groups and providing bicycle rental for exploring the surrounding countryside.
Vino Suite - Pienza
9.6 82 reviews

Vino Suite

apartment, San Quirico d'Orcia
VINO SUITE is a centrally located apartment in San Quirico d'Orcia, just 3.3 miles from Bagno Vignoni and 13 miles from Bagni San Filippo, offering easy access to the charming village and its surrounding attractions. The property has received excellent ratings for location, cleanliness, and user experience.
This 80 square metre apartment features a private entrance and a well-equipped kitchen with a dishwasher and oven, as well as a comfortable living area with a sofa, a flat-screen TV, and a desk. Guests can also enjoy the convenience of a mini-market within the apartment complex, air conditioning, free Wi-Fi, and a private bathroom with a bidet, hairdryer, and free toiletries.
Agriturismo Sant'agostino - Pienza
8.6 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.
Spectacular View 4br House_ Fenced Park And Garden - Pienza
10 1 review

Spectacular View 4br House_ Fenced Park And Garden

apartment, Torrita di Siena
This modern Tuscan villa is located in a panoramic position in Torrita di Siena, offering views of Pienza and Montepulciano, and is within walking distance of the medieval village of Montefollonico.
This family-friendly holiday home sleeps up to 10 guests across three bedrooms and three bathrooms, featuring a private fenced park, air conditioning on the first floor, a fitness room, laundry facilities, and wheelchair-accessible ground floor with an independent entrance.

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

La Casa Nel Borgo - Pienza
9.8 955 reviews

La Casa Nel Borgo

house, Pienza
La Casa nel Borgo is situated in Monticchiello, a charming village just 10.5 kilometres from Pienza and 43 kilometres from Mount Amiata, offering a peaceful escape while being within easy reach of popular destinations. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house provides a comfortable and well-equipped space for your stay, featuring a private garden and a terrace. It includes modern amenities such as air conditioning, free Wi-Fi, a washing machine, and a fully equipped kitchen with a dishwasher.
Apartment 'Villa Tiberini 1' With Panoramic View, Shared Pool And Wi-fi - Pienza
No reviews

Apartment 'Villa Tiberini 1' With Panoramic View, Shared Pool And Wi-fi

apartment, Torrita di Siena
This two-bedroom apartment in Torrita di Siena is situated a few kilometres from Montepulciano, offering panoramic views of the lake and mountains, and is within easy reach of the Church of San Francesco and Palazzo Piccolomini.
Guests can enjoy amenities including a shared outdoor pool (April-October), tennis court, garden, and Wi-Fi, with options for wine tastings and gastronomic experiences at Villa Tiberini Wine Relais, accommodating up to six people with a private kitchen and complimentary breakfast.
Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Master Double Bedroom With Pr - Pienza
No reviews

Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Master Double Bedroom With Pr

house, Trequanda
Cignella Villa Limone, a three-bedroom villa in Trequanda, Tuscany, is situated near the Val di Chiana valley and within 15km of the Saints Peter and Andrew Church, the Sant'Anna in Camprena Monastery, Triacca Winery and Enoteca Di Ghino.
This 156 square metre property sleeps six, boasting three bathrooms, a private garden, swimming pool, fully equipped kitchen, fireplace, and parking; it also offers internet access and is pet-friendly.
Residence Hill - Pienza
9.8 148 reviews

Residence Hill

apartment, San Quirico d'Orcia
Residence Hill is a spacious apartment located just 5.3 kilometres from Bagno Vignoni, a charming village known for its natural hot springs, and 45 kilometres from Siena's Piazza del Campo, offering a peaceful retreat in the Tuscan countryside. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This three-bedroom apartment, spanning 160 square metres, features a fully equipped kitchen, two living rooms, and a private hot tub. Guests can enjoy a range of amenities, including a shared kitchen and lounge, a terrace, a swimming pool, a spa, a tennis court, and free Wi-Fi.

Best pet friendly Pienza holiday rentals

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

Appartamento Acacia - Pienza
No reviews

Appartamento Acacia

apartment, Pienza
This Tuscan countryside dwelling offers panoramic views of the Val d'Orcia, a UNESCO World Heritage site renowned for its rolling hills and cypress trees, located just a short drive from Pienza.
This 2-bedroom, 1-bathroom flat accommodates up to 5 guests, featuring a kitchen with a fridge, internet, a garden, swimming pool, and parking, making it ideal for families and pet owners seeking an authentic Italian experience with unforgettable sunsets.
Podere Casa Rossa A Pienza - Pienza
9.4 38 reviews

Podere Casa Rossa A Pienza

apartment, Pienza
Podere Casa Rossa a Pienza is located in Pienza, just 13km from the picturesque village of Bagno Vignoni and 43km from the scenic Mount Amiata. This property has received excellent ratings for location, cleanliness and overall experience.
The apartment offers a spacious 150 square metre layout with 4 bedrooms and 3 bathrooms, comfortably accommodating up to 15 guests. This family-friendly accommodation features a fully equipped kitchen, a private garden, a terrace, a shared lounge, a Jacuzzi, bike rental, a fireplace and free parking.
Camera Il Giardino - Pienza
10 1 review

Camera Il Giardino

gîte, Pienza
This Val d'Orcia farmhouse, a short drive from Pienza, offers a taste of authentic Tuscan life in a UNESCO World Heritage site.
The self-catering property sleeps three, boasting a bedroom, bathroom, garden access, a swimming pool, and includes complimentary breakfast and local wine tasting.
A Casa Di Gabri - Pienza
9.4 10 reviews

A Casa Di Gabri

house, Torrita di Siena
This charming holiday home is located in Montefollonico, a peaceful village just a short drive from Torrita di Siena, offering easy access to the town's shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house provides ample space for up to five guests, with three bedrooms, two bathrooms, and a total floor area of 100 square metres. Guests can enjoy a fully equipped kitchen, a relaxing garden, and a terrace for outdoor dining, as well as free Wi-Fi access throughout the property.
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