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.

Il Colombaiolo - Pienza
9.0 172 reviews
Pienza
30/09 – 03/10
£129/nighttotal: £387 (3 )

Il Colombaiolo

2 4
farm , Trequanda
Il Colombaiolo is a farm stay in Castelmuzio, a short distance from Bagno Vignoni (19 km) and Montepulciano Terme (24 km), offering a peaceful rural setting in the Tuscan countryside. The property has received very good ratings for location and user experience, with an excellent cleanliness rating.
The farm stay has one bedroom and one bathroom, accommodating up to two guests. The property offers a seasonal outdoor pool, free Wi-Fi, free private parking, a relaxing garden, and is conveniently located near Perugia San Francesco d'Assisi Airport.
Chalet Cigno - Apartment In Tuscany - Pienza
Pienza
23/10 – 24/10
£161/nightfor 1 night

Chalet Cigno - Apartment In Tuscany

2 2
chalet , Trequanda
Chalet Cigno, a detached holiday home in Trequanda, offers convenient access to shopping at Valdichiana Outlet Village and Piazza Italia, and is within easy reach of the Historic Centre of Pienza and Val di Chiana, all within a 15 kilometre radius.
This 70 square metre, two-bedroom cottage accommodates up to three guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, private garden, and access to resort common areas including a swimming pool, with underfloor heating ensuring comfort throughout the year.
6br Val D'orcia Villa | Pool, Gym & Views - Pienza
10 1 review
Pienza
16/08 – 19/08
£1251/nighttotal: £3753 (3 )

6br Val D'orcia Villa | Pool, Gym & Views

6 13
house , Sarteano
Villa Monticelli, part of the Away from the Flock brand, is a six-bedroom luxury property situated in the Tuscan countryside between Sarteano and Radicofani, offering breathtaking views of the Val d'Orcia.
This spacious villa sleeps 13 guests and boasts an infinity pool, two-acre grounds, a fully equipped kitchen with two dishwashers and two ovens, and access to on-site activities including cooking classes and cultural excursions.
Agriturismo Selvoli - La Scuola - Pienza
9.8 65 reviews
Pienza
21/07 – 22/07
£146/nightfor 1 night

Agriturismo Selvoli - La Scuola

1 2
cabin , Pienza
This pet-friendly studio apartment, a former schoolhouse near Selvoli, is a short distance from Pienza.
The self-contained property offers a well-equipped kitchenette, bathroom with shower, a French-size bed (190x160cm), private garden, and sleeps two, ideal for couples seeking a peaceful base to explore Pienza.

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

Il Giardino Del Cardinale - Deb's Monticchiello - Pienza
10 89 reviews
Pienza
19/08 – 22/08
£748/nighttotal: £2244 (3 )

Il Giardino Del Cardinale - Deb's Monticchiello

3 4
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.
Villa Cielo- Cignella Resort Tuscany Accommodation - Pienza
Pienza
10/10 – 12/10
£253/nighttotal: £506 (2 )

Villa Cielo- Cignella Resort Tuscany Accommodation

3 5
house , Trequanda
This spacious 160 square meter villa, located in Trequanda, offers panoramic views of the Tuscan hills and is situated within the Cignella Resort, providing convenient access to local attractions such as the Artemisia Gallery and Palazzo Borgia. This family-friendly property accommodates up to six guests across three bedrooms, features a fully equipped kitchen with a dishwasher and washing machine, air conditioning, Wi-Fi, and access to resort common areas including a swimming pool and gardens, with parking available.
Agriturismo Pascianella Appartamento Bel Tramonto - Pienza
10 4 reviews
Pienza
10/07 – 12/07
£225/nighttotal: £450 (2 )

Agriturismo Pascianella Appartamento Bel Tramonto

2 2
farm , Trequanda
Agriturismo Pascianella Appartamento bel tramonto, near Castelmuzio in Tuscany, offers a peaceful countryside escape approximately 22.5km from Bagno Vignoni and 50km from Piazza Grande.
This two-bedroom, two-bathroom property boasts a 15 square metre floor area, sleeps six guests, and includes a kitchenette with oven and fridge, private parking, Wi-Fi, a garden, barbecue facilities, and a satellite TV.
80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Pienza
9.8 47 reviews
Pienza
30/09 – 03/10
£164/nighttotal: £492 (3 )

80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 4
farm , Pienza
Farm listing for up to 4 people with an excellent rating of 98% based on 47 reviews. This accommodation is located in Pienza.
Facilities and services include a terrace, a kitchen and a solarium. This accommodation is ideal for families.

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

Villa Tiberini Wine Relais - Pienza
9.6 12 reviews
Pienza
13/07 – 15/07
£195/nighttotal: £390 (2 )

Villa Tiberini Wine Relais

1 2
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.
80 M² House ∙ 2 Bedrooms ∙ 4 Guests - Pienza
Pienza
26/07 – 02/08
£97/nighttotal: £679 (7 )

80 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Trequanda
This recently renovated two-bedroom apartment, offering countryside views from its windows, is located in a quiet spot within a small village in Trequanda, providing convenient walking access to local amenities and public transport.
This 80 square meter dwelling accommodates up to four guests and features a fully equipped modern kitchen, a cozy lounge, a ground floor bedroom with a queen-size bed, a modern bathroom, and a second bedroom with two single beds and an en-suite bathroom, with self check-in available.
Suite Gioconda A Pienza - Pienza
9.5 24 reviews
Pienza
09/07 – 10/07
£203/nightfor 1 night

Suite Gioconda A Pienza

2 2
house , Pienza
Suite Gioconda in Pienza offers a self-catering property near Bagno Vignoni (12.7km) and Mount Amiata (43.5km), popular tourist destinations in Tuscany.
This 80-square-metre house features two bedrooms, one bathroom with a hot tub, a private garden with outdoor seating, free Wi-Fi, free parking, and sleeps up to seven guests.
Villa Mulinello, View Of Montepulciano - Pienza
Pienza
07/09 – 18/09
£173/nighttotal: £1903 (11 )

Villa Mulinello, View Of Montepulciano

3 2
house , Torrita di Siena
Villa Mulinello, near Montepulciano (16km from its thermal baths), offers a peaceful Tuscan retreat close to Torrita di Siena, with Bagno Vignoni and Bagni San Filippo further afield at 26km and 37km respectively.
This 93 square metre property boasts three bedrooms, two bathrooms, and sleeps six, featuring a fully equipped kitchen, terrace, garden, free parking, and Wi-Fi; barbecue facilities are also available for al fresco dining.

Best Pienza villas and holiday homes with a garden

Agriturismo Bagnolo - Pienza
9.0 235 reviews
Pienza
02/08 – 05/08
£88/nighttotal: £264 (3 )

Agriturismo Bagnolo

1 1
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.
Pienza Romantica Valdorcia La Torre Di S.guglielmo - Pienza
9.7 103 reviews
Pienza
10/07 – 12/07
£123/nighttotal: £246 (2 )

Pienza Romantica Valdorcia La Torre Di S.guglielmo

1 2
gîte , Pienza
This charming tower house is located just 600 metres from the historic walls of Pienza, in the heart of the stunning Val d'Orcia. This property has consistently received excellent ratings for location, cleanliness and user experience.
The self-catering accommodation sleeps two guests and features a spacious garden with olive trees, perfect for relaxing and enjoying the Tuscan sunshine. Enjoy modern amenities like Wi-Fi, Netflix, and a coffee machine, as well as breakfast provisions and walking trails starting directly from the property.
Apartment In A Hotel "Villa Cielo" With Shared Pool, Private Terrace & Wi-fi - Pienza
Pienza
10/10 – 12/10
£273/nighttotal: £546 (2 )

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

3 5
house , Trequanda
This 156 square meter, 3-bedroom, 2-bathroom villa apartment, accommodating up to 6 guests, is located within the 'Villa Cielo' hotel in Trequanda, offering a resort-like atmosphere and convenient access to local cultural landmarks such as the Artemisia Gallery and Palazzo Borgia, with Florence and Siena approximately 60 kilometers and 40 kilometers away respectively. Guests can enjoy a shared seasonal swimming pool (April to November), a private terrace and balcony, air conditioning, internet, a fully equipped kitchen including a fridge, microwave oven, and dishwasher, and 2 dedicated parking spaces, with pets allowed for a fee and a baby cot available.
Agriturismo Sant'ansano - Pienza
9.4 86 reviews
Pienza
29/08 – 02/09
£293/nighttotal: £1172 (4 )

Agriturismo Sant'ansano

2 2
farm , Castiglione d'Orcia
Agriturismo Sant'Ansano is a farmhouse stay in Castiglione d’Orcia, Tuscany, located 9.2km from Bagno Vignoni and 30.6km from Mount Amiata.
This air-conditioned property offers a swimming pool, garden, free Wi-Fi, and barbecue facilities, along with a kitchen equipped with a fridge, microwave, and dishwasher; pets are welcome.
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