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Pienza villas
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19 Villa rentals in Pienza

Browse Vacation Homes in the Historic District of Pienza

Booking central vacation homes in Pienza ensures seamless sightseeing, placing top-rated restaurants and downtown landmarks steps away.

Agriturismo Podere San Gregorio - Pienza
9.2 219 reviews

Agriturismo Podere San Gregorio

farm, Pienza
Agriturismo Podere San Gregorio is a charming farmhouse located just outside Pienza, a short walk from the town center and a short drive from Montepulciano and Siena. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This farmhouse features one bedroom with wood-beamed ceilings and terracotta floors. Guests can enjoy a peaceful garden with BBQ facilities, a complimentary breakfast basket, free Wi-Fi, and free parking.
Apartment "Agriturismo Il Casato Mag-il Vaglio" With Mountain View, Terrace And Wi-fi - Pienza
10 2 reviews

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

farm, Pienza
This Pienza farm stay, a smoke-free rental house, offers convenient access to Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile, all within a 10-minute walk.
The 750-square-foot (approximately 70-square-meter) property features two bedrooms, one bathroom, and accommodates four guests, including amenities such as air conditioning, a terrace, a garden, parking, and a kitchen equipped with a refrigerator and microwave; barbecue grills are available for guest use.
Colombaiolo - Pienza
9.0 4 reviews

Colombaiolo

farm, Pienza
Agriturismo Colombaiolo, a historic stone farmhouse dating to the late 1400s, offers a prime panoramic location just 0.3 miles from Pienza and 400 yards from the Pieve di Corsignano church, providing stunning views of the Val d'Orcia and Monte Amiata. This renovated agriturismo, set within a nature reserve, features spacious rooms, on-site parking, air conditioning, internet, and a daily breakfast with local products, making it an ideal base for exploring UNESCO sites like Pienza and Montepulciano, with relaxation opportunities by the farm's pond.
135 M² Farmhouse ∙ 2 Bedrooms ∙ 8 Guests - Pienza
9.9 6 reviews

135 M² Farmhouse ∙ 2 Bedrooms ∙ 8 Guests

farm, Pienza
Agriturismo Il Casato Mag-il Giogo, a farmhouse rental near Pienza, Italy, is located one kilometer from Pienza's historic center and offers easy access to Val d'Orcia attractions such as the Vitaleta Chapel (4.3 miles), Bagno Vignoni (6.2 miles), and Montepulciano (9.3 miles).
This 1450-square-foot property features two bedrooms, two bathrooms, and sleeps up to eight guests, boasting amenities like a terrace, garden, barbecue, table tennis, and parking, plus access to local produce and guided tours.

Best family friendly Pienza villas and beach houses

Among the 19 accommodations in Pienza, here are the 4 best family friendly villas and beach houses

Pienza Romantica Valdorcia La Torre Di S.guglielmo - Pienza
9.7 107 reviews

Pienza Romantica Valdorcia La Torre Di S.guglielmo

gîte, Pienza
Torre di San Guglielmo is a charming cottage located just a short walk from the historic center of Pienza, nestled in the breathtaking Val d'Orcia. This cottage has received excellent reviews for its location, cleanliness, and overall experience.
Torre di San Guglielmo is a cozy cottage that can accommodate up to two guests. It has a modern kitchen with a fridge and microwave, a comfortable bedroom, and a bathroom. Guests can enjoy a relaxing breakfast in the garden, take advantage of the Wi-Fi and Netflix, or explore the nearby town of Pienza.
Didi House - Pienza
9.5 19 reviews

Didi House

house, Montepulciano
Didi House is situated in the heart of Montepulciano, within walking distance of major tourist attractions and landmarks. It has excellent user and location ratings.
The house has a floor area of 1360 square feet, 2 bedrooms, 1 bathroom, and a guest capacity of 4. It features a fully equipped kitchen, a private balcony with stunning garden views, and a spacious terrace and garden. Guests can also enjoy free private parking, WiFi, and a bicycle rental service.
Agriturismo Palazzo Conti - B - Pienza
8.0 94 reviews

Agriturismo Palazzo Conti - B

farm, San Quirico d'Orcia
Agriturismo Palazzo Conti - B is located in Pienza, a charming town in the Val d'Orcia, just 22 miles from Siena and 29 miles from Arezzo, making it a perfect base for exploring the Tuscan countryside. This farm stay consistently receives high ratings for its cleanliness, location, and overall experience.
This rural retreat offers a peaceful escape for up to four guests. The farm features a private swimming pool, a garden, a terrace, free parking, and Wi-Fi, allowing you to relax and enjoy the beautiful surroundings.
House ∙ 1 Bedroom ∙ 3 Guests - Pienza
No reviews

House ∙ 1 Bedroom ∙ 3 Guests

house, Montepulciano
House rental for up to 3 people. You will stay in Montepulciano.
Services and facilities: a swimming pool, a kitchen and a washing machine. This house in Montepulciano also has a terrace!

Frequently Asked Questions about villa rentals in Pienza

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

    The Val d'Orcia is a great place to spot wildlife. You might see red deer, wild boar, and even the occasional fox or hare. You can also find a variety of birds, including hawks, owls, and woodpeckers.
  • 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 is the best time to visit Pienza?

    Spring and fall are the best times to visit Pienza. The weather is mild, and the crowds are smaller. You'll enjoy beautiful wildflowers in the spring and stunning fall foliage. Summer can be very hot and crowded, and winter can be chilly.
  • 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.

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

    You'll find the best deals on villa rentals in Pienza during the shoulder seasons, spring and fall. Summer is the peak season, so expect higher prices and fewer availability. If you're looking for the best value, book early, especially for the summer months.
  • 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.

  • What are the top hiking trails near Pienza?

    The Sentiero del “Percorso Natura” is a great trail that winds through the Val d'Orcia, offering stunning views. Another popular trail is the “Sentiero delle Crete Senesi,” which takes you through the unique landscape of the Crete Senesi.
  • 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 advantages of renting a house or a villa in Pienza

    Renting a villa in Pienza gives you the freedom to cook your own meals, relax in your own space, and enjoy the privacy of your own garden or patio. It's also a great way to experience the local culture and enjoy the stunning views of the Val d'Orcia.
  • 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.

  • Are there popular destinations near Pienza?

    Absolutely! The beautiful hill town of Montepulciano is just a short drive away, known for its wine and stunning views. Siena, a larger city, is also within easy reach and offers a rich history and beautiful architecture. You can also visit the charming towns of Montalcino and San Quirico d'Orcia, both within a 30-minute drive.
  • 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.

Popular destinations

Best Pienza houses with a garden

La Casa Nel Borgo - Pienza
9.8 954 reviews

La Casa Nel Borgo

house, Pienza
La Casa nel Borgo is located in the tranquil village of Monticchiello, just a short drive from Pienza, a UNESCO World Heritage Site, and a 6.5-mile drive from Montepulciano Terme. This charming house has received excellent ratings for its cleanliness, location, and overall experience.
The house features a fully equipped kitchen, a comfortable seating area, a private bathroom, and a private entrance. Guests can enjoy air conditioning, free Wi-Fi, and a terrace offering breathtaking views of the surrounding countryside.
Villa Oliveta, View Of Montepulciano - Pienza
No reviews

Villa Oliveta, View Of Montepulciano

house, Torrita di Siena
Villa Oliveta, located in Torrita di Siena, offers stunning views of Montepulciano and is conveniently situated about 10 miles from Montepulciano Terme and 16 miles from Bagno Vignoni.
This 1400-square-foot vacation home features three bedrooms, three bathrooms, and a private garden with barbecue facilities, accommodating up to six guests and including amenities such as a dishwasher, Wi-Fi, and free parking.
Agriturismo Marinello - Pienza
9.4 603 reviews

Agriturismo Marinello

farm, Pienza
Agriturismo Marinello is located in the Val d'Orcia, a UNESCO World Heritage site, just 2.5 miles from the center of Pienza and a short drive from other Tuscan towns like Montepulciano and Montalcino. The farm has earned excellent ratings for its location, cleanliness, and overall experience.
The farm offers a variety of rooms and apartments, all featuring comfortable furnishings and private bathrooms. Amenities include a swimming pool, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher.
Holiday Home Haus Banditello- Blick Auf Das Tal Von Montepulciano By Interhome - Pienza
No reviews

Holiday Home Haus Banditello- Blick Auf Das Tal Von Montepulciano By Interhome

house, Torrita di Siena
This holiday house in Montefollonico is 8.9 miles from Montepulciano Terme and 15 miles from Bagno Vignoni, offering valley views of Montepulciano.
This 1400 square foot dwelling accommodates up to 11 guests with 3 bedrooms, 2 bathrooms, a fully equipped kitchenette, a fireplace, and a garden.

Best Pienza houses with parking

Podere Manafiore - Pienza
9.7 3 reviews

Podere Manafiore

house, Pienza
Podere Manafiore, near Monticchiello, is a 7100-square-foot (660 square meter) villa conveniently located about 7.7 miles from Montepulciano Terme and 28 miles from Mount Amiata.
This six-bedroom, eight-bathroom estate sleeps 19 guests and boasts a private pool with a pool table, a well-equipped kitchen, free Wi-Fi, and free private parking, plus a terrace, garden, and concierge service.
Villa Petroio By Maneri  Luxury In Val Dorcia - Pienza
10 2 reviews

Villa Petroio By Maneri Luxury In Val Dorcia

house, Trequanda
This private hilltop estate in Petroio, a district of Trequanda, offers panoramic views of olive groves and rolling hills, with rural access roads leading to the peaceful countryside.
This villa accommodates up to 20 guests with 7 bedrooms and 7 bathrooms, featuring a fully equipped kitchen, a private pool, bocce court, and ample parking, ideal for large group gatherings.
Casa Oliveto - Pienza
9.9 14 reviews

Casa Oliveto

house, Trequanda
Casa Oliveto, a three-bedroom, three-bathroom home in Trequanda, Italy, offers an authentic Tuscan experience near the Val d'Orcia UNESCO World Heritage site.
This vacation rental sleeps six guests and includes a kitchen with a refrigerator, freezer, and dishwasher; parking is also available.
Agriturismo Cantagalli - Pienza
9.6 372 reviews

Agriturismo Cantagalli

farm, San Quirico d'Orcia
Agriturismo Cantagalli, in San Quirico d'Orcia, Italy, offers stunning city views and is conveniently located 24 miles from Mount Amiata and 29 miles from Piazza del Campo.
This family-friendly farmhouse boasts a terrace, garden, restaurant, tennis court, and features like a fully equipped kitchen, air conditioning, free Wi-Fi, and free parking, plus on-site activities including table tennis, darts, and bike rentals.

Check Out Vacation Homes with a Pool in Pienza

Having a pool at your vacation home in Pienza lets you enjoy a proper swim in the city without any extra planning.

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Pienza
9.4 21 reviews

50 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Castiglione d'Orcia
Poggio Ai Gelsi - Pienza
9.3 591 reviews

Poggio Ai Gelsi

house, Pienza
Apartment Azzurro- Cignella Resort Tuscany - Pienza
No reviews

Apartment Azzurro- Cignella Resort Tuscany

chalet, Trequanda
Agriturismo Selvoli - La Civetta - Pienza
10 29 reviews

Agriturismo Selvoli - La Civetta

gîte, Pienza

Search 5-Star Holiday Houses in Pienza

Luxury vacation homes in Pienza feature high-end finishes and prime locations. Enjoy designer decor in a carefully considered private stay.

Casa Aldobrandesca - Pienza
10 3 reviews

Casa Aldobrandesca

house, Castiglione d'Orcia

Find the Best Holiday Houses with Jacuzzi in Pienza

Enjoy a private hot tub at your city vacation home in Pienza. These properties offer a secluded soak after a day of exploration.

Agriturismo Palazzo Conti A - Pienza
9.3 145 reviews

Agriturismo Palazzo Conti A

house, San Quirico d'Orcia
Tuscan Relais Il Serraglio - Pienza
9.8 622 reviews

Tuscan Relais Il Serraglio

farm, Montepulciano
Agriturismo Il Macchione - Pienza
9.3 571 reviews

Agriturismo Il Macchione

house, Pienza
30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
9.4 21 reviews

30 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Castiglione d'Orcia
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