Villas and Holiday homes in Pienza

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Pienza holiday homes
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12 Villa rentals in Pienza

Compare Holiday Homes with a Pool in Pienza

Every holiday home with a pool in Pienza ensures that a proper swim in the heart of the city is always an effortless option.

Agriturismo Chiancianello - Pienza
9.9 213 reviews
Pienza
06/09 – 08/09
£152/nighttotal: £304 (2 )

Agriturismo Chiancianello

1 2
gîte , Pienza
Agriturismo Chiancianello is a short 15-20 kilometre drive from the charming hilltop towns of Pienza, Montepulciano, and Montalcino, nestled in the beautiful Val d'Orcia region. This property enjoys excellent ratings for cleanliness, location and user experience.
The accommodation offers comfortable, fully equipped apartments with a choice of bedrooms and living spaces. Guests can enjoy a range of amenities including a shared pool, a sauna, a garden, and a children's playground, as well as access to bikes for exploring the region.
Podere Lamone, Casale Completo, Pienza - Pienza
10 13 reviews
Pienza
07/12 – 10/12
£381/nighttotal: £1143 (3 )

Podere Lamone, Casale Completo, Pienza

1 8
gîte , Pienza
This Val d'Orcia farmhouse, a short drive from Pienza and Montepulciano, offers a tranquil escape in the Tuscan countryside.
Sleeping eight guests, this self-catering holiday home boasts four bedrooms, six bathrooms, a private garden with barbecue, sun loungers, and access to a shared swimming pool with panoramic Val d'Orcia views; plus Wi-Fi, parking and locally sourced produce are available.
Agriturismo Selvoli - Bruco - Pienza
9.9 20 reviews
Pienza
30/09 – 03/10
£283/nighttotal: £849 (3 )

Agriturismo Selvoli - Bruco

1 4
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).
Agriturismo Palazzi Del Papa Val D'orcia Pienza - Pienza
9.9 190 reviews
Pienza
16/08 – 19/08
£2071/nighttotal: £6213 (3 )

Agriturismo Palazzi Del Papa Val D'orcia Pienza

1 13
gîte , Pienza
Palazzi del Papa is a farmhouse located in the Val d'Orcia, just a few kilometres from the charming hilltop town of Pienza, within the Natural Reserve of Lucciola Bella. The property has received excellent ratings for location, cleanliness, and overall user experience.
This farmhouse offers nine rooms, accommodating up to 18 guests, perfect for families or groups. Guests can enjoy a swimming pool, garden, and private access to the entire property, including Wi-Fi and table tennis, as well as breakfast and dinner featuring fresh, locally-sourced produce from the farm.

Best family friendly Pienza villas and holiday home

Among the 8 accommodations in Pienza, here are the 4 best family friendly villas and holiday homes

110 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests - Pienza
9.8 23 reviews
Pienza
27/08 – 31/08
£317/nighttotal: £1268 (4 )

110 M² Farmhouse ∙ 3 Bedrooms ∙ 7 Guests

3 2
farm , Pienza
Farm for up to 7 guests with an excellent rating of 98% based on 23 reviews. You will be in Pienza.
Facilities and services: a dish washer, free parking and a freeze. Enjoy a swimming pool in this accommodation in Pienza!
Agriturismo Poderino - Pienza
9.3 411 reviews
Pienza
28/07 – 31/07
£269/nighttotal: £807 (3 )

Agriturismo Poderino

3 5
farm , San Quirico d'Orcia
Agriturismo Poderino is situated in San Quirico d'Orcia, Tuscany, 42 kilometers from Mount Amiata and 48 kilometers from Piazza del Campo in Siena. This farmhouse enjoys a peaceful setting in the Tuscan countryside, offering stunning views and a tranquil atmosphere. It has received excellent user ratings for location and cleanliness, as well as a very good rating overall.
The farmhouse offers a range of amenities, including a hot tub, an outdoor fireplace, and a terrace or balcony. Guests can also enjoy cycling and hiking opportunities in the surrounding area, with bicycle rental services available.
Monastero Sant'anna In Camprena - Pienza
9.6 340 reviews
Pienza
08/07 – 12/07
£176/nighttotal: £704 (4 )

Monastero Sant'anna In Camprena

1 2
farm , Pienza
Fattoria Monastero Sant'Anna in Camprena is located in the Tuscan countryside, just 19 kilometres from Bagno Vignoni and 23 kilometres from Montepulciano Terme, offering a peaceful escape from the hustle and bustle of Pienza. This farm stay has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The property features a charming restaurant, a garden and a terrace, providing ample space for relaxing and enjoying the beautiful surroundings. This farm stay can accommodate up to two guests in its comfortable and modern accommodation, which includes air conditioning, a private bathroom, a fridge, a microwave oven and free Wi-Fi.
Apartment In A Hotel "Villa Salvia" With Shared Pool, Private Terrace & Wi-fi - Pienza
Pienza
02/07 – 03/07
£710/nightfor 1 night

Apartment In A Hotel "Villa Salvia" With Shared Pool, Private Terrace & Wi-fi

3 2
house , Trequanda
This detached villa is located in Trequanda, offering convenient access to cultural sites such as Artemisia Gallery and Palazzo Borgia, and within driving distance of Siena (approximately 72 kilometres) and Florence (approximately 120 kilometres).
This 156 square meter villa accommodates up to six guests across three bedrooms and three bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a terrace, a shared swimming pool open seasonally, and parking, with pets permitted for an additional fee.

Frequently asked questions about villa rentals in Pienza

  • What are the must-see attractions in and around Pienza?

    You absolutely must visit the Duomo, a stunning example of Renaissance architecture, and the Palazzo Piccolomini, a grand palace offering beautiful views of the Val d'Orcia. For a taste of local life, head to the Piazza Pio II, the heart of Pienza, where you can enjoy the local atmosphere. Just a short drive away, you can explore the enchanting medieval village of Monticchiello, known for its charming streets and annual theatre festival.
  • What are the best holiday homes in Pienza?

    Among the holiday homes in Pienza, Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Pienza?

    The Val d'Orcia is home to a variety of wildlife, including wild boars, deer, and foxes. You might also spot birds of prey like buzzards and kestrels soaring above the rolling hills. If you're lucky, you might even catch a glimpse of a rare Italian wolf, but remember to keep a safe distance.
  • What are the best holiday homes with a pool in Pienza?

    Agriturismo Il Macchione, Poggio Ai Gelsi and Agriturismo La Collina are the best holiday homes with a pool in Pienza.

  • What is the best time to visit Pienza?

    Spring and autumn are the best times to visit Pienza, as the weather is mild and the crowds are smaller. You can enjoy the beautiful scenery without the summer heat or winter chill. The countryside is particularly stunning in autumn, when the leaves turn vibrant shades of red, orange, and yellow.
  • What are the best holiday homes with a jacuzzi in Pienza?

    The best holiday homes with a jacuzzi in Pienza are Agriturismo Il Macchione, Poggio Ai Gelsi and Villa I Cipressini Piscina Riscaldata Spa Toscana.

  • When is it easiest to book a villa rental in Pienza?

    Booking a villa rental in Pienza is easiest outside of peak season, which is typically July and August. If you're flexible with your travel dates, you can find great deals on villa rentals in the shoulder seasons, such as April-May or September-October.
  • What are the best holiday homes for families and kids in Pienza?

    The best holiday homes for families and kids in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati.

  • What are the top hiking trails near Pienza?

    The Sentiero del Cassia, a scenic trail that winds through the Val d'Orcia, offers breathtaking views of the rolling hills and vineyards. For a shorter hike, you can explore the trails around the Monte Amiata, a volcanic mountain with stunning views of the surrounding countryside. Remember to wear sturdy hiking shoes and bring plenty of water.
  • What are the best pet friendly holiday homes in Pienza?

    The best pet friendly holiday homes in Pienza are Agriturismo Il Macchione, La Casa Nel Borgo and Poggio Ai Gelsi.

  • What are the advantages of renting a house or a villa in Pienza

    Renting a villa gives you the freedom and privacy to enjoy your holiday at your own pace. You can cook your own meals, relax in your private garden, and enjoy the peace and quiet of the countryside. It's also a great option for families or groups of friends who want to spend quality time together.
  • What are the best holiday homes with parking in Pienza?

    Agriturismo Il Macchione, La Casa Nel Borgo and Agriturismo Riposati are the best holiday homes with parking in Pienza.

  • Are there popular destinations near Pienza?

    Pienza is a great base for exploring the region of Tuscany. Within a short drive, you can visit the charming hilltop town of Montepulciano, famous for its Vino Nobile wine, or the historic city of Siena, known for its stunning Piazza del Campo. You can also explore the beautiful vineyards and olive groves of the Val d'Orcia, a UNESCO World Heritage site.

Destinations nearby

Best Pienza villas and holiday homes with parking

Agriturismo Bonello - Pienza
9.4 920 reviews
Pienza
08/07 – 12/07
£410/nighttotal: £1640 (4 )

Agriturismo Bonello

1 2
farm , Pienza
Agriturismo Bonello is a historic farmhouse located just outside Pienza, a charming medieval town, with stunning views of the Val D’Orcia nature reserve, a UNESCO World Heritage Site, and a short drive from Siena. The property has excellent user, location and cleanliness ratings.
The farmhouse offers a range of self-catering apartments, each with a fully equipped kitchen. Guests can enjoy a refreshing dip in the outdoor pool, relax in the Jacuzzi, or unwind in the sauna and spa.
Podere Travagliola - Pienza
9.8 19 reviews
Pienza
29/06 – 02/07
£116/nighttotal: £348 (3 )

Podere Travagliola

1 3
farm , Castiglione d'Orcia
Podere Travagliola is a farm stay located in Castiglione d'Orcia, just 5.6 km from the thermal baths of Bagno Vignoni and 33.8 km from Mount Amiata, offering a peaceful escape in the Tuscan countryside. This property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The farm stay features a single bedroom and bathroom, covering 13 square metres and accommodating up to 2 guests. Guests can enjoy a fully equipped kitchen, air conditioning, a garden, and free parking, along with scenic views and opportunities for hiking and cycling in the surrounding area.
Agriturismo 'Villa Agriturismo Il Pratone' With Mountain View, Private Pool And Wi-fi - Pienza
9.6 5 reviews
Pienza
26/06 – 29/06
£209/nighttotal: £627 (3 )

Agriturismo 'Villa Agriturismo Il Pratone' With Mountain View, Private Pool And Wi-fi

2 4
house , Castiglione d'Orcia
This Castiglione d’Orcia villa, near the Fortress of Tentennano (1.1 km) and Piazza delle Sorgenti (4 km), offers a secluded mountain setting with stunning views.
The 100 square metre property sleeps six, boasting three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher and fridge, a private pool, garden, parking, and free Wi-Fi.
Villa Il Moro - Pienza
8.6 7 reviews
Pienza
16/09 – 19/09
£836/nighttotal: £2508 (3 )

Villa Il Moro

5 4
house , Montalcino
Villa il Moro, a spacious 550 square metre property in Montalcino, Tuscany, is situated 45km from Siena’s Piazza del Campo and within easy reach of other Tuscan towns such as Bagno Vignoni.
This five-bedroom, six-bathroom villa sleeps up to 19 guests and boasts a private swimming pool, terrace, garden, free Wi-Fi, and ample parking, ideal for large families or groups seeking a self-catering holiday with access to hiking and cycling in the Tuscan countryside.

Best Pienza villas and holiday homes with a garden

Capanne Di Sopra - Pienza
Pienza
17/08 – 19/08
£345/nighttotal: £690 (2 )

Capanne Di Sopra

3 4
house , Torrita di Siena
This detached villa in Capanne di Sopra, Montefollonico, is located 14.3 kilometres from Montepulciano Terme and 24.1 kilometres from Bagno Vignoni, with Bagni San Filippo a further 37 kilometres away.
This pet-friendly property accommodates up to 12 guests across 3 bedrooms, offering free WiFi, private parking, a dishwasher, and access to a garden, with a 10:00 AM check-out.
Agriturismo Renello - Pienza
9.0 117 reviews
Pienza
10/10 – 12/10
£343/nighttotal: £686 (2 )

Agriturismo Renello

3 5
house , Torrita di Siena
Agriturismo Renello is located in Petroio, in the Tuscan countryside, 15km from Montepulciano and a 45-minute drive from Lake Trasimeno, offering a peaceful retreat amongst rolling hills. This property has received excellent user and location ratings, as well as a very good cleanliness rating.
This rural retreat offers comfortable rooms with seating areas and en suite bathrooms. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden with BBQ facilities, a restaurant serving regional cuisine, a fitness center, a tennis court, and free Wi-Fi, parking, and bike rentals.
Villa Fonte All'oppio Con Area Piscina Recintata - Pienza
8.5 46 reviews
Pienza
18/08 – 22/08
£309/nighttotal: £1236 (4 )

Villa Fonte All'oppio Con Area Piscina Recintata

2 4
house , Pienza
Villa Fonte all'Oppio is situated in the Tuscan countryside, just a short drive from the charming town of Pienza, a UNESCO World Heritage Site, and a little further from Montepulciano. The property has received very good ratings for cleanliness and user experience, and its location is considered excellent.
The villa offers spacious apartments with fireplaces, equipped kitchens, and private bathrooms. Guests can enjoy a refreshing dip in the private pool, relax in the lush garden, and prepare delicious meals using the provided BBQ facilities.
Agriturismo Casalpiano - Pienza
9.7 153 reviews
Pienza
09/07 – 19/07
£160/nighttotal: £1600 (10 )

Agriturismo Casalpiano

1 3
farm , Pienza
Agriturismo Casalpiano, a family-friendly farmhouse in Pienza, enjoys a convenient location, 12.4km from Montepulciano Terme and 14.3km from Bagno Vignoni, both renowned for their thermal baths, and 45km from Mount Amiata.
This self-catering property offers a private entrance, swimming pool, garden, free parking, Wi-Fi, and outdoor play equipment, perfect for families exploring the Tuscan countryside.
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