Compare cheap villa rentals in Pienza from 100+ sites!

19 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Pienza villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Apartment "Agriturismo Il Casato Mag-il Torchio" With Mountain Views, Terrace And Wi-fi - Pienza
10 6 reviews

Apartment "Agriturismo Il Casato Mag-il Torchio" With Mountain Views, Terrace And Wi-fi

farm, Pienza
This Pienza farm stay, a smoke-free rental, is conveniently located within a 10-minute walk of Palazzo Borgia, Pienza Cathedral, and Palazzo Vescovile.
This 750-square-foot (approximately 70-square-meter) one-bedroom, one-bathroom house sleeps four and features a kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and barbecue grills; guests can explore Pienza's historic center on foot.
Agriturismo Il Casato - Il Torchio - Pienza
10 7 reviews

Agriturismo Il Casato - Il Torchio

gîte, Pienza
This Pienza vacation rental, near the Vitaleta Chapel (4.3 miles), offers easy access to Val d'Orcia attractions like Bagno Vignoni (6.2 miles) and Montepulciano (9.3 miles).
The 753-square-foot apartment sleeps four, features a private outdoor area with a barbecue, and includes amenities such as Wi-Fi, air conditioning, a washing machine, and a ping-pong table; plus, options for breakfast and local tours are available.
70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
10 6 reviews

70 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Pienza
Agriturismo Il Casato - Il Torchio, a rural getaway located one kilometer from Pienza's historic center, offers breathtaking Val d'Orcia views and easy access to Montepulciano (9 miles) and Montalcino (16 miles).
This 810-square-foot farmhouse rental sleeps four, features one bedroom and bath, a full kitchen with modern appliances, air conditioning, a terrace, and a private outdoor area with a barbecue; on-site amenities include a table tennis table, and guests can arrange guided winery tours and rent electric bikes.
Il Nido - Pienza
9.6 50 reviews

Il Nido

house, Pienza
Il Nido, a Pienza vacation rental, is situated 6.3 miles from Bagno Vignoni, 10 miles from Montepulciano Terme, and 16 miles from Bagni San Filippo, offering easy access to Tuscany's thermal baths and medieval towns.
This 910-square-foot (approximately 85-square-meter) house features two bedrooms, one bathroom, and accommodates up to seven guests, complete with a fully equipped kitchen, Wi-Fi, a fireplace, a washing machine, and a peaceful garden with a terrace.

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

200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
No reviews

200 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

house, Torrita di Siena
Villa Tiberini - Casale il Pecino, a villa in Torrita di Siena within the Tiberini Estate in Montepulciano, offers access to Valdichiana and Val d'Orcia, with mountain and city views.
This 2,150 sq ft villa accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a private pool and garden, on-site parking, Wi-Fi for video calls, and barbecue facilities, plus shared amenities at the estate including a communal kitchen and playground, along with optional wine tastings and estate product samplings.
Villa ∙ 6 Bedrooms ∙ 12 Guests - Pienza
No reviews

Villa ∙ 6 Bedrooms ∙ 12 Guests

house, Pienza
This spacious, independent villa is located in a quiet district just outside Pienza's historic center, offering convenient access to the Val d'Orcia, a UNESCO World Heritage site renowned for its iconic landscapes.
Accommodating up to 12 guests, this villa features 6 bedrooms, 6 bathrooms, multiple living areas with fireplaces, a well-equipped kitchen with an espresso maker, a 4x12 meter swimming pool open from May to October, an annex with a double bedroom and en-suite, an outdoor wood-burning oven and barbecue, complimentary Wi-Fi, and parking.
Agriturismo Collosodo - Pienza
9.8 108 reviews

Agriturismo Collosodo

farm, Pienza
Agriturismo Collosodo is located in the Tuscan countryside, just under a mile from the medieval village of Monticchiello and a 15-minute drive from Pienza. The farm offers a private seasonal pool, a garden with a barbecue, and a working farm experience for guests to enjoy.
Il Giardino Del Cardinale - Deb's Monticchiello - Pienza
9.9 96 reviews

Il Giardino Del Cardinale - Deb's Monticchiello

house, Pienza
Il Giardino del Cardinale, located in Monticchiello near Pienza, offers easy access to Montepulciano (6.5 miles) and Bagno Vignoni (8.2 miles), allowing for convenient exploration of Tuscany's renowned hilltop towns and thermal springs.
This 3770-square-foot (350-square-meter) villa features three bedrooms, four bathrooms, two living rooms, a private terrace, and a garden, accommodating families or groups comfortably, with amenities including a fully equipped kitchen, air conditioning, free Wi-Fi, and on-site restaurant and mini-market.

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

Il Colombaiolo - Pienza
9.1 154 reviews

Il Colombaiolo

farm, Trequanda
Il Colombaiolo is a farm stay located in Castelmuzio, a village near Trequanda, about 12 miles from Bagno Vignoni and 15 miles from Montepulciano Terme, offering a peaceful escape in the Tuscan countryside. The property has received very good ratings for location, cleanliness, and overall experience.
This rural retreat features one bedroom and one bathroom, comfortably accommodating two guests. Enjoy a refreshing dip in the seasonal outdoor pool, relax in the garden, and stay connected with free Wi-Fi, all while being conveniently located near major roads for easy exploration.
Apartment Azzurro- Cignella Resort Tuscany - Pienza
No reviews

Apartment Azzurro- Cignella Resort Tuscany

chalet, Trequanda
Apartment Azzurro- Cignella Resort Tuscany in Osteria Delle Noci is 29 miles from Piazza Grande and 11 miles from Montepulciano Terme, offering a pet-friendly chalet experience in Trequanda.
This 1270 sq ft chalet accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, a full kitchen, free WiFi, a private entrance, a garden, a swimming pool, and a patio with outdoor furniture, located 50 miles from Perugia San Francesco d'Assisi Airport.
Casa D'orcia - Pienza
9.4 11 reviews

Casa D'orcia

house, Pienza
Casa d'Orcia, a renovated vacation rental in Pienza, Italy, is 4.7 miles from Bagno Vignoni and 24 miles from Mount Amiata.
This 700-square-foot (approximately 65 square meter) house sleeps four guests and features two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, a private plunge pool, a Jacuzzi, and free Wi-Fi; packed lunches are provided for excursions.
Casa Al Poggio - Pienza
9.6 26 reviews

Casa Al Poggio

house, Castiglione d'Orcia
This Tuscan farmhouse apartment near Castiglione d'Orcia, Italy provides easy access to nearby towns like Pienza and San Quirico in the Val d'Orcia region.
The 850-square-foot rental features two bedrooms, one bathroom, and a living kitchen with a fireplace, comfortably accommodating four guests and offering amenities such as internet, parking, and pet-friendliness.

Best Pienza houses with parking

Masseria Del Bosco Poderuccio - Pienza
8.0 74 reviews

Masseria Del Bosco Poderuccio

farm, Chianciano Terme
Masseria del Bosco Poderuccio, a rural retreat in Chianciano Terme, Italy, is conveniently located 16 miles from Montepulciano Terme, 8 miles from Bagno Vignoni, and 25 miles from Mount Amiata, offering easy access to Tuscan attractions.
This one-bedroom, one-bathroom farmhouse rental boasts 170 square feet of living space, featuring a private entrance, garden views, a swimming pool, free Wi-Fi, and free parking; amenities include a microwave, coffee machine, and kettle.
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 a short drive from the charming towns of Siena and Saturnia, surrounded by the rolling hills of the Tuscan countryside. It boasts excellent ratings for location, cleanliness, and user experience.
The farm features a range of amenities that cater to both relaxation and exploration, including a swimming pool, a spa, a restaurant, and a fitness center. Guests can also enjoy the convenience of free Wi-Fi and parking, as well as comfortable accommodations with modern amenities.
Agriturismo Bombina - Pienza
9.5 145 reviews

Agriturismo Bombina

farm, Montalcino
Agriturismo Bombina is located in Montisi, a charming village in the Val d'Orcia, a short drive from the thermal baths of Bagno Vignoni and Montepulciano Terme. The farm consistently receives excellent ratings for its location, cleanliness, and overall experience.
The accommodations are spacious and comfortable, featuring fully equipped kitchens and private bathrooms. Guests can enjoy a variety of amenities, including a swimming pool, a garden, and a terrace, as well as activities like packed lunches and an outdoor fireplace.
Villa I Cipressini Piscina Riscaldata Spa Toscana - Pienza
10 105 reviews

Villa I Cipressini Piscina Riscaldata Spa Toscana

house, Pienza
Villa I Cipressini, near Pienza, Italy, is located 30 miles from Mount Amiata and 8.5 miles from Bagno Vignoni.
This 5,380-square-foot luxury villa boasts five bedrooms, seven bathrooms, a private heated pool and spa, a fitness center, and ample amenities for up to ten guests, perfect for family vacations or group getaways in Tuscany.

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.

Agriturismo Palazzo Conti A - Pienza
9.3 140 reviews

Agriturismo Palazzo Conti A

house, San Quirico d'Orcia
95 M² Farmhouse ∙ 3 Bedrooms ∙ 6 Guests - Pienza
9.4 19 reviews

95 M² Farmhouse ∙ 3 Bedrooms ∙ 6 Guests

farm, Montepulciano
Agriturismo 'Villa Agriturismo Il Pratone' With Mountain View, Private Pool And Wi-fi - Pienza
9.6 5 reviews

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

house, Castiglione d'Orcia
Chalet Cigno Cignella Resort - Pienza
No reviews

Chalet Cigno Cignella Resort

chalet, Trequanda

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.

Poggio Ai Gelsi - Pienza
9.2 603 reviews

Poggio Ai Gelsi

house, Pienza

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.

Monastero Sant'anna In Camprena - Pienza
9.6 430 reviews

Monastero Sant'anna In Camprena

farm, Pienza
Agriturismo Poderino - Pienza
9.5 185 reviews

Agriturismo Poderino

farm, San Quirico d'Orcia
L’ Aia Del Principe - Pienza
9.6 301 reviews

L’ Aia Del Principe

farm, Montepulciano
Romantic Cottage With Hot Tub  Val D'orcia - Pienza
8.6 39 reviews

Romantic Cottage With Hot Tub Val D'orcia

cottage, Torrita di Siena
©2026 cozycozy.com