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

Tenuta Santo Pietro - Pienza
9.3 810 reviews

Tenuta Santo Pietro

farm, Pienza
Tenuta Santo Pietro is a working farm located just three miles from the historic town of Pienza, nestled in the Tuscan countryside. The farm enjoys excellent ratings for its location, cleanliness, and overall experience.
The farmhouse dates back to the 13th century and has been beautifully restored, featuring terracotta floors and exposed wooden beams. Guests can enjoy a swimming pool, a restaurant serving traditional Tuscan cuisine, and a range of activities including wine and olive oil tastings, as well as exploring the peaceful gardens.
La Corte Antica Appartamento " Il Chiassino" - Pienza
10 13 reviews

La Corte Antica Appartamento " Il Chiassino"

apartment, Pienza
Il Chiassino apartment is centrally located in Pienza's historic centre, a short walk from Piazza Pio II.
This two-bedroom, two-bathroom flat sleeps three guests, offering a fully equipped kitchen with dishwasher, private parking 0.25km away, and a three-story layout comprising a ground floor kitchen, first-floor single bedroom and bathroom, and a second-floor double bedroom and bathroom.
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.
The Garden Of The Oaks (Podere Santa Caterina) - Pienza
10 34 reviews

The Garden Of The Oaks (Podere Santa Caterina)

gîte, San Quirico d'Orcia
This three-bedroom farmhouse wing, sleeping six, is situated in the Val d'Orcia park, a five-minute walk from Bagno Vignoni's historic thermal baths.
The self-catering property boasts a private courtyard, solarium, fully equipped kitchen, two bathrooms, and offers local culinary tastings, excursions to Siena and other Tuscan towns, and activities including electric bike hire and truffle hunting.

Best Pienza holiday rentals with parking

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.
Azienda Agricola Poderuccio - Pienza
9.0 96 reviews

Azienda Agricola Poderuccio

farm, Pienza
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.
Samsara Apartment Elegant Apartment In The Historical Center. - Pienza
10 3 reviews

Samsara Apartment Elegant Apartment In The Historical Center.

apartment, Pienza
This Pienza apartment, a 5-minute walk from the Pienza Cathedral and Palazzo Piccolomini, offers easy access to key historical sites.
The 65-square-metre flat features two bedrooms, one bathroom, sleeps five, and includes amenities such as Wi-Fi, a Smart TV, a fully equipped kitchen, and a BBQ.
Casa Isma - Pienza
8.1 26 reviews

Casa Isma

apartment, Castiglione d'Orcia
Casa Isma is a self-catering apartment situated in Castiglione d'Orcia, a charming medieval town, just 5.1 kilometres from the famous thermal baths of Bagno Vignoni. It has received very good user ratings and excellent location and cleanliness ratings.
The apartment has one bedroom and one bathroom, covering 43 square metres and accommodating up to four guests. It offers a shared kitchen and lounge, a private entrance, a mini-market on site, free Wi-Fi, and a flat-screen TV.

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

Molino Della Tuoma - Pienza
8.6 10 reviews

Molino Della Tuoma

apartment, San Quirico d'Orcia
Molino della Tuoma, a self-catering apartment in San Quirico d’Orcia, enjoys a tranquil setting near the river, 42km from Mount Amiata and 43km from Siena's Piazza del Campo.
This five-guest property boasts a private garden, terrace, jacuzzi, and spa, plus a fully equipped kitchenette, washing machine, and free Wi-Fi and parking.
Villa ∙ 7 Bedrooms ∙ 14 Guests - Pienza
No reviews

Villa ∙ 7 Bedrooms ∙ 14 Guests

house, Montepulciano
This expansive villa is located in a district of Montepulciano providing easy access to the town's historic centre, a UNESCO World Heritage site renowned for its Renaissance architecture.
Offering accommodation for up to 14 guests, this property features seven bedrooms, multiple well-equipped kitchens including one with seating for 20, a swimming pool, Jacuzzi, air conditioning, and WIFI throughout, with six bedrooms boasting ensuite bathrooms and several with whirlpool bathtubs.
La Tresa Country Living - Pienza
9.2 45 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.
Chalet Cigno - Pienza
No reviews

Chalet Cigno

apartment, Trequanda
Chalet Cigno is located in Trequanda, 18km from Montepulciano Terme and 48km from Piazza Grande in Arezzo.
This 70 square metre chalet has two bedrooms, a private pool, a fully equipped kitchen and free parking, making it ideal for families or groups of friends seeking a relaxing Tuscan retreat.

Best pet friendly Pienza holiday rentals

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

Locanda Di Montisi Piazza Room Between The Hills Of Montalcino - Pienza
No reviews

Locanda Di Montisi Piazza Room Between The Hills Of Montalcino

apartment, Montalcino
This one-bedroom flat is located in the medieval village of Montisi, offering easy access to Siena (approximately 45 kilometres away), Arezzo, Pienza, Montalcino, and Montepulciano, making it an ideal base for exploring the Crete Senesi region.
This pet-friendly accommodation for two includes air conditioning, Wi-Fi, and a workspace, with opportunities for outdoor pursuits such as thermal baths, food and wine tours, and cycling routes readily available.
Montepulcianolettings House - Pienza
10 3 reviews

Montepulcianolettings House

apartment, Montepulciano
This three-bedroom house, perfect for families, is centrally located in Montepulciano's historic centre, offering easy walking access to all major sights.
The property features a fully equipped kitchen, two ensuite bedrooms, and a spacious studio apartment with a double bed and sofa bed, accommodating up to six guests; no lift is present.
Stunning Private Villa For 5 People With A/c, Wifi, Tv, Patio, Pets Allowed And Panoramic View - Pienza
No reviews

Stunning Private Villa For 5 People With A/c, Wifi, Tv, Patio, Pets Allowed And Panoramic View

apartment, Torrita di Siena
This holiday home in Torrita di Siena enjoys a peaceful garden setting, situated close to the Val di Chiana and within 10km of the Church of St Agnes, Colonna del Marzocco, Palazzo Avignonesi, and Triacca Winery.
The 100 square metre property offers three bedrooms, two bathrooms, sleeping up to five guests, and boasts a fully equipped kitchen with microwave and dishwasher, plus a terrace, garden, parking, and free Wi-Fi.
Pienzalettings - Pienza
9.5 281 reviews

Pienzalettings

apartment, Pienza
This Pienza apartment is located in the town centre, just a short walk from the Duomo and Piazza del Popolo, and 45 kilometres from Mount Amiata. The property has received excellent ratings for location, cleanliness, and overall user experience.
The accommodation has a private bathroom, a kitchen with a fridge, freezer, and microwave, and a terrace or balcony. Guests can enjoy a garden, parking, and free Wi-Fi, as well as the option to dine al fresco.
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