Holiday Rentals in Pienza

69 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 69 accommodations in Pienza, here are the 4 best family friendly rentals

Le Checche - Pienza
9.6 217 reviews
Pienza
27/06 – 04/07
SG$541/nighttotal: SG$3787 (7 )

Le Checche

1 2
farm , Pienza
Le Checche is a farm stay situated 35 kilometres from Mount Amiata, near Pienza, with Bagno Vignoni 8.7 kilometres away and Bagno San Filippo 16 kilometres distant.
This family-friendly property offers a range of amenities including a swimming pool, hot tub, restaurant, and outdoor play equipment, making it a perfect choice for families seeking a relaxing rural retreat.
Dolce Pienza – Modern Home In The Historic Center - Pienza
10 18 reviews
Pienza
27/06 – 29/06
SG$459/nighttotal: SG$918 (2 )

Dolce Pienza – Modern Home In The Historic Center

1 2
apartment , Pienza
This Pienza apartment, situated in the historic centre, offers easy walking access to Piazza Pio II and the Duomo.
Sleeping up to five guests, the self-catering flat features a master bedroom, a fully equipped kitchen with fridge and freezer, air conditioning, and parking; a bathroom with bathtub and bidet completes this one-bedroom property.
Apartment Montello 1 - Pienza
9.9 70 reviews
Pienza
10/07 – 12/07
SG$290/nighttotal: SG$580 (2 )

Apartment Montello 1

1 2
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.
Il Tramonto Di Pienza - Pienza
9.0 4 reviews
Pienza
28/07 – 31/07
SG$342/nighttotal: SG$1026 (3 )

Il Tramonto Di Pienza

2 5
house , Pienza
Pienza Apartment with garden is situated in Pienza, Tuscany, offering easy access to local attractions in the historic town centre.
This 60 square metre house sleeps nine guests and features a fully equipped kitchen with dishwasher, air conditioning, a private garden with outdoor dining, free parking, and Wi-Fi.

Best Pienza holiday rentals with parking

Locanda In Tuscany - Pienza
9.4 131 reviews
Pienza
09/07 – 10/07
SG$416/nightfor 1 night

Locanda In Tuscany

1 2
farm , Castiglione d'Orcia
The Locanda in Tuscany is a rural retreat situated just 3.1 miles from the charming town of Castiglione d'Orcia and 16 miles from the historic Montepulciano, making it an ideal base for exploring the beautiful Tuscan countryside. This farm stay consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers a range of accommodation options, each featuring charming wood-beamed ceilings and a choice of bed linens. Guests can enjoy the on-site restaurant, relax by the outdoor pool and garden, or participate in activities like cooking classes, horse riding, and mushroom picking.
200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
Pienza
25/07 – 30/07
SG$1804/nighttotal: SG$9020 (5 )

200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , Torrita di Siena
Villa Tiberini - Casale il Pecino, located within the Tiberini Estate in Montepulciano, offers a rural retreat in Torrita di Siena with mountain and city views, situated a short distance from the historic centre of Montepulciano. This 200 square meter villa accommodates up to eight guests across four bedrooms and four bathrooms, boasting a private outdoor pool and garden, barbecue facilities, and access to shared amenities at Villa Tiberini Wine Relais including a communal kitchen and playground, with opportunities for wine tastings and local produce sampling.
Frattina1860 - Pienza
9.3 12 reviews
Pienza
27/06 – 04/07
SG$197/nighttotal: SG$1379 (7 )

Frattina1860

1 2
apartment , Montalcino
This holiday let in Montisi provides easy access to Bagno Vignoni at 21 kilometres and Montepulciano Terme at 26 kilometres, with Siena landmarks approximately 45-48 kilometres away.
This 36 square metre one-bedroom flat accommodates two guests and features a garden, private parking, free Wi-Fi, a kitchen with an oven and microwave, air conditioning, and an outdoor dining area.
La Chiusa Dei Monaci - Pienza
9.1 180 reviews
Pienza
05/08 – 08/08
SG$192/nighttotal: SG$576 (3 )

La Chiusa Dei Monaci

1 3
farm , Trequanda
La Chiusa dei Monaci is a farm stay located in Castelmuzio, a small village near Trequanda, just 50 km from both Siena and Arezzo, offering a peaceful escape from the hustle and bustle. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The farm stay offers a 40 square metre, one-bedroom apartment with a fully equipped kitchen, perfect for a family of four. Guests can enjoy the private terrace with stunning views, the garden, and barbecue facilities for al fresco dining.

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.

Destinations nearby

Best Pienza holiday rentals with a balcony

Apartment "Agriturismo Il Casato Mag-il Giogo" With Mountain View, Terrace And Wi-fi - Pienza
10 4 reviews
Pienza
27/06 – 28/06
SG$1216/nightfor 1 night

Apartment "Agriturismo Il Casato Mag-il Giogo" With Mountain View, Terrace And Wi-fi

2 4
farm , Pienza
This Pienza farmhouse, a 135-square-metre self-catering holiday home, enjoys a peaceful mountain setting less than a kilometre from Pienza's historic centre, including Palazzo Borgia, the Pienza Cathedral, and Palazzo Vescovile.
Sleeping up to eight guests in two bedrooms and two bathrooms, the property boasts a terrace, garden, parking, air conditioning, and a fully equipped kitchen (including fridge and microwave), plus barbecue facilities for al fresco dining.
Le Corolle - Pienza
9.1 137 reviews
Pienza
27/06 – 29/06
SG$240/nighttotal: SG$480 (2 )

Le Corolle

2 2
house , Montepulciano
Le Corolle is a holiday home located just 2 kilometres outside of Montepulciano, offering a peaceful retreat close to the town's attractions. The property has consistently received excellent ratings for location, cleanliness and overall user experience.
The self-catering accommodation features a well-equipped kitchenette, a private bathroom, a terrace and a garden. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace, cook up a meal on the barbecue, or make use of the free private parking.
110 M² Apartment ∙ 3 Bedrooms ∙ 6 Guests - Pienza
Pienza
27/06 – 28/06
SG$722/nightfor 1 night

110 M² Apartment ∙ 3 Bedrooms ∙ 6 Guests

3 4
apartment , San Quirico d'Orcia
This three-bedroom, two-bathroom Tuscan apartment is located in San Quirico d'Orcia, surrounded by gardens and offering easy access to the region's green hills and villas, with free parking at the entrance.
This 110 square meter holiday home accommodates up to six guests and features a fully equipped kitchen with a dining table for eight, a living room with a fireplace, and a terrace or balcony, with pets welcome.
Agriturismo Palazzo Conti A - Pienza
9.2 143 reviews
Pienza
29/06 – 02/07
SG$394/nighttotal: SG$1182 (3 )

Agriturismo Palazzo Conti A

2 3
house , San Quirico d'Orcia
Agriturismo Palazzo Conti A is located just outside Pienza, a short drive from Montalcino, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartments are classically decorated and feature flat-screen TVs, seating areas, and fully equipped kitchenettes. Guests can enjoy a range of amenities including a swimming pool, a natural pool, a garden with BBQ facilities, a spa, a restaurant, a bar, and room service.

Best pet friendly Pienza holiday rentals

Among the 69 accommodations in Pienza, here are the 4 best pet friendly rentals

Apartment Azzurro- Cignella Resort Tuscany - Pienza
9.3 6 reviews
Pienza
09/08 – 10/08
SG$415/nightfor 1 night

Apartment Azzurro- Cignella Resort Tuscany

2 4
apartment , Torrita di Siena
Apartment Azzurro is located in the Cignella district, just a short distance from the historic centre of Torrita di Siena, offering stunning views of the Tuscan countryside.
This two-bedroom, two-bathroom property sleeps four guests and boasts a private terrace with countryside views, a fully equipped kitchen, and a swimming pool, making it perfect for families or groups of friends.
Appartamento La Serra - Pienza
9.4 7 reviews
Pienza
21/07 – 23/07
SG$141/nighttotal: SG$282 (2 )

Appartamento La Serra

1 2
apartment , Pienza
This Pienza apartment, ideally located within easy reach of the town's attractions (though precise distances aren't specified), offers a private garden perfect for al fresco dining.
The self-catering flat features a loft-style bedroom, a fully equipped kitchenette, a private bathroom, air conditioning, and accommodates two guests.
Locanda Di Montisi  Castello Room Among The Hills Of Montalcino - Pienza
Pienza
21/07 – 22/07
SG$244/nightfor 1 night

Locanda Di Montisi Castello Room Among The Hills Of Montalcino

1 2
apartment , Montalcino
This one-bedroom flat is located in the medieval village of Montisi, within the Crete Senesi region, offering convenient access to Siena (50 km), Arezzo (65 km), Pienza (20 km), Montalcino (15 km), and Montepulciano (25 km).
This accommodation for three guests features Tuscan-style decor, exposed beams, terracotta floors, air conditioning, Wi-Fi, a workspace, and allows one pet for an additional fee, with street parking and self check-in available.
Agriturismo San Marcello - Pienza
9.4 699 reviews
Pienza
29/08 – 02/09
SG$353/nighttotal: SG$1412 (4 )

Agriturismo San Marcello

1 2
farm , Castiglione d'Orcia
Agriturismo San Marcello is located in Castiglione d'Orcia, a short drive from the thermal baths of Bagno Vignoni and Bagni San Filippo, offering a peaceful escape in the Tuscan countryside. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The farm offers spacious accommodation units, some with fully equipped kitchens and private bathrooms. Guests can enjoy a continental breakfast, relax on the sun terrace, or explore the surrounding area with skiing and cycling opportunities.
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