Villas and Holiday homes in Pienza

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Pienza villas
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19 Villa rentals in Pienza

Best Pienza villas and holiday homes with a pool

Among the 19 accommodations in Pienza, here are the 4 best villas and holiday homes with a pool

Chalet "Villa Falco" With Shared Pool, Private Terrace & Wi-fi - Pienza
No reviews

Chalet "Villa Falco" With Shared Pool, Private Terrace & Wi-fi

house, Trequanda
This villa in Trequanda is located near Chiesa di San Francesco and Palazzo Piccolomini, providing access to the Val di Chiana and historic towns such as Pienza and Montepulciano.
This 142 m² property offers accommodation for four guests with two bedrooms and two bathrooms, featuring air conditioning, Wi-Fi, a dishwasher, and a shared swimming pool open from April 7 to November 2, with parking for two vehicles and pet-friendly options available.
Casale Il Gugnolo - Pienza
9.3 6 reviews

Casale Il Gugnolo

house, Castiglione d'Orcia
This four-bedroom villa, located in Castiglione d'Orcia, is situated 32 kilometres from Mount Amiata and 3.06 kilometres from Bagno Vignoni.
This 200 square metre holiday home accommodates up to 15 guests and offers a fully equipped kitchen, three bathrooms, a Jacuzzi, garden, terrace, fireplace, and free Wi-Fi, with bike rental and nearby cycling and walking tours available.
Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
No reviews

Villa Basilico - Cignella Resort Chalet In Tuscany

chalet, Trequanda
This chalet in Trequanda is located near cultural sites such as the Artemisia Gallery and Palazzo Borgia, and historical landmarks including Chiesa di San Francesco and Palazzo Piccolomini, offering a gateway to the region's heritage.
This 93 square meter property accommodates up to four guests across two bedrooms and two bathrooms, featuring a well-equipped kitchen, air conditioning, Wi-Fi, a swimming pool, and a terrace, with parking available.
100 M² Villa ∙ 2 Bedrooms ∙ 6 Guests - Pienza
9.2 6 reviews

100 M² Villa ∙ 2 Bedrooms ∙ 6 Guests

house, Castiglione d'Orcia
Villa Agriturismo Il Pratone is situated in Castiglione d'Orcia, Tuscany, offering a peaceful retreat amidst olive groves, vineyards, and oak forests.
This 100 square metre farmhouse boasts two bedrooms, two bathrooms, and can comfortably accommodate up to six guests, featuring a private fenced pool (open May 1st to October 31st), a fully equipped kitchen with dishwasher, and on-site parking for three vehicles.

Best family friendly Pienza villas and holiday home

Among the 19 accommodations in Pienza, here are the 4 best family friendly villas and holiday homes

Wp Relais Villa Vignalunga - Pienza
10 56 reviews

Wp Relais Villa Vignalunga

house, Castiglione d'Orcia
This luxurious villa in Castiglione d'Orcia enjoys a tranquil riverfront location, within 5km of the Tentennano Fortress and Piazza delle Sorgenti, and 10km from Horti Leonini and Palazzo Chigi.
The 400 square metre property boasts four bedrooms, six bathrooms, sleeps eight guests, and includes a private pool, Jacuzzi, and a fully equipped kitchen; plus an arcade/game room.
55 M² Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Pienza
10 1 review

55 M² Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Pienza
Farm rental for 3 guests with an excellent rating of 100% based on 1 reviews. You will be based in Pienza.
Services and facilities: a garden, a barbecue and a kitchen. This is a pet-friendly accommodation!
Agriturismo Zampugna - Pienza
9.4 646 reviews

Agriturismo Zampugna

farm, Trequanda
Agriturismo Zampugna is situated in Montefollonico, a charming village just a short drive from Trequanda and approximately 52 miles from Perugia San Francesco d'Assisi Airport. The farm stay has received excellent ratings for its location, cleanliness and overall user experience.
The property offers a peaceful garden and a private entrance for a relaxing stay. Guests can enjoy a swimming pool with stunning views, a terrace, barbecue facilities, a picnic area, a restaurant and free parking.
Poggio Ai Gelsi - Pienza
9.2 603 reviews

Poggio Ai Gelsi

house, Pienza
Poggio ai Gelsi is a holiday home located in Pienza, just 40km from Siena, offering stunning views of the Val d'Orcia. This property has received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features private bathrooms, air conditioning, comfortable bedding, and a kitchen equipped with a fridge, microwave, and dishwasher. Guests can enjoy the private pool, terrace, garden, and parking, as well as the nearby attractions of Pienza's historic centre.

Frequently asked questions about villa rentals in Pienza

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

    You simply must visit the Duomo, with its stunning Renaissance architecture, and the Palazzo Piccolomini, offering breathtaking views of the Val d'Orcia. For a unique experience, explore the underground tunnels of the town's historic water system. Just outside Pienza, the rolling hills of the Val d'Orcia offer picturesque landscapes and charming medieval villages like Monticchiello and San Quirico d'Orcia.
  • What are the best villa rentals in Pienza?

    Among the villa rentals 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 red deer, wild boar, and a variety of bird species. If you're lucky, you might even spot a golden eagle soaring overhead. Keep your eyes peeled for hares and foxes as well, especially in the early morning or late evening.
  • What are the best villa rentals with a pool in Pienza?

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

  • What is the best time to visit Pienza?

    Spring (April-May) and autumn (September-October) offer the most pleasant weather for exploring the region. The landscape is vibrant and green in spring, while autumn brings warm days and stunning colours. Summer can be hot and crowded, but the warm weather is ideal for swimming in the nearby Lago Trasimeno.
  • What are the best villa rentals with a jacuzzi in Pienza?

    The best villa rentals 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 during the shoulder seasons (April-May and September-October). You'll find better prices and fewer crowds compared to the peak season (June-August). Booking well in advance is always recommended, especially for popular periods like Easter and Christmas.
  • What are the best villa rentals for families and kids in Pienza?

    The best villa rentals 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 follows an ancient Roman road through the Val d'Orcia, is a popular choice. The Via Francigena, a historic pilgrimage route, also passes through the area, offering breathtaking views and charming villages along the way. For a shorter hike, explore the trails around the Sanctuary of Sant'Anna in Camprena, just outside Pienza.
  • What are the best pet friendly villa rentals in Pienza?

    The best pet friendly villa rentals 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 offers a more private and spacious experience compared to a hotel. You'll have your own kitchen, living space, and outdoor areas, giving you the flexibility to create your own schedule and enjoy meals at your own pace. Many villas also come with amenities like a swimming pool and a garden, perfect for relaxing and enjoying the Tuscan countryside.
  • What are the best villa rentals with parking in Pienza?

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

  • Are there popular destinations near Pienza?

    Absolutely! The charming hilltop town of Montepulciano, known for its excellent wine, is just a short drive away. Siena, with its iconic Piazza del Campo, is another popular destination, offering a glimpse into the rich history and culture of Tuscany. For a day trip, consider visiting the beautiful city of Perugia, perched on a hill overlooking the Umbrian countryside.

Popular destinations

Best Pienza villas and holiday homes with parking

Agriturismo Cavalierino - Pienza
9.4 272 reviews

Agriturismo Cavalierino

farm, Montepulciano
Agriturismo Cavalierino is located in the countryside outside Montepulciano, about 4.6 miles from the town's thermal baths and 31 miles from Mount Amiata, offering a peaceful escape from the bustling town centre. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The property features a swimming pool, jacuzzi, terrace, garden, and fitness centre, providing ample opportunities for relaxation and recreation. Guests can enjoy a daily Italian breakfast and select rooms offer kitchenettes, allowing for self-catering options.
Agriturismo Belagaggio - Pienza
9.5 522 reviews

Agriturismo Belagaggio

farm, Torrita di Siena
Agriturismo Belagaggio is located in Montefollonico, a picturesque village just a short drive from Torrita di Siena, offering stunning views of the surrounding countryside. The property has received excellent ratings for its location, cleanliness and overall experience.
This recently renovated farmhouse offers comfortable accommodation with a range of amenities including a swimming pool, jacuzzi, and terrace. Guests can enjoy a restaurant serving local cuisine, a spa, and a variety of activities such as cycling and hiking.
Monastero Sant'anna In Camprena - Pienza
9.6 430 reviews

Monastero Sant'anna In Camprena

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.
157 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
No reviews

157 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

house, Pienza
This Tuscan farmhouse, situated in the Val d'Orcia near Monticchiello (5 minutes drive), is 13km from Pienza and 5km from Montepulciano, offering easy access to these renowned Renaissance towns.
This 157 square metre property boasts four bedrooms, four bathrooms, and sleeps eight, featuring a private pool, Jacuzzi, and a 1000 sq m garden with barbecue – perfect for a relaxing Tuscan escape.

Best Pienza villas and holiday homes with a garden

Villa 'Tiberini - Casale Il Pecino' With Panoramic Valdichiana View, Private Pool & Wi-fi - Pienza
No reviews

Villa 'Tiberini - Casale Il Pecino' With Panoramic Valdichiana View, Private Pool & Wi-fi

house, Torrita di Siena
This private villa is situated in Torrita di Siena, a few kilometres from Montepulciano, offering convenient access to Valdichiana and Val d'Orcia, with historical sites such as the Church of San Francesco and Palazzo Piccolomini, and natural attractions like the Historic Centre of Pienza, within easy reach.
This four-bedroom, four-bathroom holiday home accommodates up to eight guests and features a private outdoor pool, garden, barbecue, high-speed Wi-Fi, and breakfast, with proximity to Villa Tiberini Wine Relais for additional amenities and opportunities for cycling and hiking.
Podere Spagliarda - Pienza
8.0 1 review

Podere Spagliarda

house, San Quirico d'Orcia
Podere Spagliarda, a rural retreat in San Quirico d'Orcia, is situated 4.2km from Bagno Vignoni and 38.6km from Mount Amiata, offering easy access to these popular Tuscan destinations.
This 140 square metre farmhouse sleeps up to 24 guests, boasting four bedrooms, four bathrooms, a private patio, swimming pool, garden, free Wi-Fi, and a fully equipped kitchen including a dishwasher and fridge.
Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany - Pienza
9.6 20 reviews

Whole Big Tuscan Villa With Pool & Vineyards In The Heart Of Tuscany

house, Pienza
This charming house is located in a peaceful rural setting, just 15 kilometres from Pienza's main attractions, including Piazza delle Sorgenti, Art Studio di Adelina Quadri, and La Foce. It has received excellent reviews from previous guests.
The house spans 400 square metres and comfortably accommodates up to 20 guests. The property features a private pool, a spacious garden, and a barbecue area, perfect for relaxing and enjoying the Tuscan sunshine.
Chalet Cigno Cignella Resort - Pienza
No reviews

Chalet Cigno Cignella Resort

chalet, Trequanda
This charming chalet is situated in Trequanda, just 18km from Montepulciano Terme and 26km from Bagno Vignoni, offering a peaceful retreat in the Tuscan countryside. The property provides a tranquil setting for exploring the region's rich history and culture.
The chalet spans 80 square metres and comfortably accommodates up to 5 guests in its two bedrooms. Enjoy a range of amenities including a shared swimming pool, a terrace with mountain views, a garden, and free Wi-Fi.
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