Villas in Pienza

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Pienza villas
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19 Villas in Pienza

Best villas and farmhouses in Pienza with a pool

Among the 19 villas in Pienza, here are the 4 best villas 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.
Villa Tiberini Appartamento 4 - Pienza
No reviews

Villa Tiberini Appartamento 4

house, Torrita di Siena
This holiday apartment is situated on the first floor in Torrita di Siena, offering easy access to local attractions and amenities.
The 46 square metre flat sleeps up to three guests in one bedroom and a living room sofa bed, featuring air conditioning, Wi-Fi, a kitchen with a fridge, freezer, and dishwasher, and a bathroom with a sensory shower, sauna, and hammam.
Well-equipped Holiday Home In Spedaletto Italy With Private Pool - Pienza
10 2 reviews

Well-equipped Holiday Home In Spedaletto Italy With Private Pool

house, Pienza
This charming holiday home is located in Ospedaletto, a peaceful district just 4.2 kilometres from Bagno Vignoni and 19 kilometres from Montepulciano Terme, making it an ideal base for exploring the beautiful Tuscan countryside. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The spacious 4-bedroom villa, with a floor area of 130 square metres, comfortably accommodates 8 guests. Enjoy a refreshing dip in the private pool, relax in the garden, and explore the surrounding area on complimentary bicycles.
Terre Di Nano - Pienza
10 19 reviews

Terre Di Nano

farm, Pienza
Terre di Nano farm, in Val d'Orcia, is situated approximately 1.6km from Monticchiello, offering stunning views of Montepulciano and Pienza.
This one-bedroom, one-bathroom self-catering apartment in a 19th-century building features terracotta floors, exposed beams, a fully equipped kitchen, fireplace, swimming pool, and on-site olive oil and Chianti Terre di Nano wine tasting and tours.

Best family friendly villas in Pienza

Among the 19 villas in Pienza, here are the 4 best family friendly villas

The Garden Of The Oaks (Podere Santa Caterina) - Pienza
10 33 reviews

The Garden Of The Oaks (Podere Santa Caterina)

farm, 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.
Podere Pratovecchio 14&2, Emma Villas - Pienza
8.9 3 reviews

Podere Pratovecchio 14&2, Emma Villas

house, Torrita di Siena
This spacious 8-bedroom villa, located in Montefollonico near Montepulciano Terme, is 14 kilometres from Montepulciano Terme and within easy driving distance of Bagno Vignoni (26 km) and Bagni San Filippo (39 km), offering easy access to Tuscany's thermal baths.
The 600 square metre property boasts a private pool, extensive garden, barbecue facilities, free Wi-Fi, and parking, comfortably accommodating large families or groups with its eight bedrooms and eight bathrooms.
Lovely Apartment With Wifi, A/c, Pool, Tv, Patio And Pets Allowed, Close To Montepulciano - Pienza
No reviews

Lovely Apartment With Wifi, A/c, Pool, Tv, Patio And Pets Allowed, Close To Montepulciano

farm, Trequanda
This farm stay is located in the Orcia Valley, a UNESCO World Heritage site, 10 kilometres from Torrita di Siena and 16 kilometres from Montepulciano, offering easy access to other Tuscan towns.
This 118 square metre agriturismo features two bedrooms and two bathrooms for up to four guests, with amenities including air conditioning, WiFi, a shared swimming pool, and the option of cooking lessons.
Apartment With Pool, A/c, Wifi, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano - Pienza
No reviews

Apartment With Pool, A/c, Wifi, Tv, Patio, Pets Allowed, Panoramic View, Close To Montepulciano

farm, Trequanda
This farm stay is situated in the Orcia Valley, 10 kilometres from Torrita di Siena and 16 kilometres from Montepulciano, offering a base for exploring this renowned tourist district.
This property provides 14 apartments across 220 square metres, accommodating up to 6 guests with 3 bedrooms and 3 bathrooms, and features a shared swimming pool, WiFi, and on-site cooking lessons.

Frequently asked questions about villa rentals in Pienza

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

    Pienza is a real gem! You absolutely must visit the Duomo, a beautiful cathedral with stunning Renaissance architecture. The Palazzo Piccolomini is another must-see, offering breathtaking views of the Val d'Orcia. And if you're looking for a unique experience, check out the Corsignano Fortress, a medieval fortress with a fascinating history.
  • What are the best villas in Pienza?

    Among the villas 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. You might spot deer, wild boar, and even the occasional fox. You're also likely to see a variety of birds, including hawks, owls, and woodpeckers. Keep an eye out for the local sheep, too, as they are a common sight in the area.
  • What are the best villas with a pool in Pienza?

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

  • What is the best time to visit Pienza?

    Spring and autumn are the best times to visit Pienza. The weather is mild, and the crowds are smaller. You'll also be able to enjoy the stunning colours of the Val d'Orcia, especially in autumn. Summer can be very hot and crowded, while winter can be chilly and wet.
  • What are the best villas with a jacuzzi in Pienza?

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

    Booking a villa rental in Pienza is easier outside of peak season. If you're looking for the best deals, try booking in the shoulder seasons of spring and autumn. You'll find that availability is better and prices are lower during these months.
  • What are the best villas for families and kids in Pienza?

    The best villas 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 Val d'Orcia is a hiker's paradise. One of the most popular trails is the Sentiero del Latte, which follows an old mule track through rolling hills and vineyards. Another great option is the Sentiero del Brunello, which takes you past vineyards and olive groves. Both offer stunning views of the Tuscan countryside.
  • What are the best pet friendly villas in Pienza?

    The best pet friendly villas 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 in Pienza offers a lot of advantages. You'll have more space and privacy than in a hotel. You'll also be able to enjoy the convenience of having a kitchen and laundry facilities. Plus, you'll be able to experience the true Tuscan lifestyle, surrounded by the beauty of the Val d'Orcia.
  • What are the best villas with parking in Pienza?

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

  • Are there popular destinations near Pienza?

    Absolutely! Pienza is a great base for exploring the surrounding area. You can easily take day trips to Siena, Montepulciano, and Montalcino, all within an hour's drive. Each town offers its own unique charm and attractions, from medieval architecture to world-class wineries.

Popular destinations

Best Pienza villas and holiday homes with parking

Villa Aquila-cignella Resort Acommodation Tuscany - Pienza
9.0 1 review

Villa Aquila-cignella Resort Acommodation Tuscany

house, Trequanda
Villa Aquila-Cignella Resort Accommodation Tuscany is located in Osteria Delle Noci, 46.7 kilometres from Piazza Grande and 17.7 kilometres from Montepulciano Terme.
This 220 square metre villa offers three bedrooms, three bathrooms, and can accommodate up to eleven guests, featuring air conditioning, a private entrance, a terrace with sea views, a garden, a private swimming pool, and a fully equipped kitchen with a dishwasher and microwave.
Mastrojanni Relais - Small Luxury Hotels Of The World - Pienza
9.7 335 reviews

Mastrojanni Relais - Small Luxury Hotels Of The World

farm, Montalcino
Mastrojanni Relais is a farm stay located in Castelnuovo dell’Abate, just 39 kilometres from both Siena and Saturnia, offering a peaceful rural setting near popular tourist destinations. The property has received excellent ratings for location, cleanliness and user experience.
The accommodation features private bathrooms, flat-screen TVs and free Wi-Fi in each room, along with a range of amenities such as a swimming pool, a sauna, a spa, a restaurant, a bar and a fitness centre. Guests can also enjoy a terrace, a garden and room service.
L’ Aia Del Principe - Pienza
9.6 301 reviews

L’ Aia Del Principe

farm, Montepulciano
L’ Aia del Principe is a farmhouse located just 6.6 kilometres from Montepulciano Terme and 21 kilometres from Bagno Vignoni, offering a peaceful retreat in the beautiful Tuscan countryside. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The farmhouse has one bedroom and one bathroom, spanning 25 square metres and accommodating up to two guests. Amenities include air conditioning, a jacuzzi, a terrace, a garden, a spa, a concierge service, parking, and free Wi-Fi, ensuring a comfortable and luxurious stay.
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.

Best Pienza villas and holiday homes with a garden

In Toscana Camere - Pienza
9.8 163 reviews

In Toscana Camere

house, Pienza
In Toscana Camere, you'll find a peaceful countryside retreat located just 10km from Pienza, a 24km drive from Montepulciano, and 48km from Montalcino. The property has received excellent ratings for cleanliness, location, and user experience.
The houses and apartments offer a blend of traditional Tuscan charm and modern amenities. Guests can enjoy a fully equipped kitchen, free Wi-Fi, air conditioning, and a garden, perfect for relaxing and enjoying the peaceful surroundings.
Agriturismo Selvoli - La Civetta - Pienza
10 30 reviews

Agriturismo Selvoli - La Civetta

gîte, Pienza
This charming one-bedroom cottage is situated in the beautiful Val d'Orcia, just 5 kilometres from both Pienza and Bagno Vignoni, two of the region's most popular destinations. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The cottage features a cosy living-dining area with a fireplace and a fully equipped kitchen, comfortably accommodating up to 3 guests. Guests can enjoy a private patio with a covered area, a barbecue, and a stunning panoramic swimming pool overlooking the Val d'Orcia and Monte Amiata during the summer months.
[15 Min From Montepulciano] Villa Chiara - Pienza
9.8 22 reviews

[15 Min From Montepulciano] Villa Chiara

house, Torrita di Siena
Villa Chiara, in the hills above Montefollonico, offers a secluded Tuscan villa experience, a short drive (approximately 20km) from both Montepulciano and Pienza.
This three-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen with balcony, private garden, parking, and internet access; nearby hiking trails and local amenities add to its appeal.
Agriturismo Castello Di Spedaletto - Pienza
9.8 371 reviews

Agriturismo Castello Di Spedaletto

farm, Pienza
Castello di Spedaletto da Laura is a peaceful farm stay situated just outside the historic town of Pienza, a 32-kilometre drive from Montepulciano and 5.5 kilometres from the Lucciolabella Natural Reserve.
The property features one-bedroom apartments with air conditioning and a swimming pool, and offers guests the chance to experience authentic Tuscan cuisine with its on-site production of olive oil, wine, pasta, and legumes.
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