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12 Villa rentals in Pienza
9.3 128 reviews
Pienza
07/13 – 07/17
$443/nighttotal: $1772 (4 )
Locanda In Tuscany
1 2
farm , Castiglione d'Orcia
The Locanda in Tuscany is a rural farmhouse located near Castiglione d'Orcia, just 3.1 miles from the town center and 16 miles from Montepulciano. This property has received excellent ratings for its location, cleanliness, and overall experience. The farmhouse features a peaceful garden, a refreshing swimming pool, and charming rooms with wood-beamed ceilings. Guests can enjoy a range of amenities, including a restaurant, bar, spa, and cooking classes, as well as activities like horseback riding and mushroom picking.
9.8 26 reviews
Pienza
07/19 – 07/23
$145/nighttotal: $580 (4 )
Agriturismo La Creta
1 2
farm , Montepulciano
Agriturismo La Creta, near Montepulciano, Italy, offers convenient access to Montepulciano Terme (4.8 miles) and Mount Amiata (31 miles). This pet-friendly farmhouse rental boasts fully equipped kitchenettes, a barbecue, and an outdoor picnic area, perfect for families seeking a relaxing getaway near Montepulciano.
9.2 616 reviews
Pienza
07/08 – 07/12
$220/nighttotal: $880 (4 )
Agriturismo Cavalierino
1 2
farm , Montepulciano
Agriturismo Cavalierino, near Montepulciano, Tuscany, offers a convenient base for exploring the region, situated 4.6 miles from Montepulciano Terme and 31 miles from Mount Amiata. This family-friendly farmhouse rental boasts a swimming pool, jacuzzi, fitness center, and fully equipped kitchenettes, along with free Wi-Fi and parking.
9.8 74 reviews
Pienza
07/13 – 07/15
$213/nighttotal: $426 (2 )
Spagna5
3 2
house , Pienza
Spagna5, a vacation home in Pienza, Tuscany, is conveniently located 9.3 miles from Bagno Vignoni, 10 miles from Montepulciano Terme, and 16 miles from Bagni San Filippo, offering easy access to popular Tuscan destinations. This 1720-square-foot house features three bedrooms, two living rooms, three bathrooms, a fully equipped kitchen with a fridge and dishwasher, air conditioning, a private balcony and terrace with garden views, free Wi-Fi, and accommodates families comfortably.
9.4 527 reviews
Pienza
07/02 – 07/03
$160/nightfor 1 night
Montorio
1 2
house , Montepulciano
This charming house sits on a peaceful hilltop just a 15-minute walk from Montepulciano's historic center, offering stunning views of the San Biagio Church and the surrounding countryside. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. The house features a spacious garden with hammocks, a gazebo, and a patio overlooking the church, perfect for relaxing and enjoying the Tuscan landscape. Guests can take advantage of amenities like a fully equipped kitchen, free Wi-Fi, private parking, a fitness center, a tennis court, and room service.
9.5 68 reviews
Pienza
07/25 – 07/28
$201/nighttotal: $603 (3 )
Casa Primavera A Rocca D'orcia
2 3
house , Castiglione d'Orcia
Casa Primavera is a charming vacation rental located in the peaceful Rocca d'Orcia district, just a short drive from the renowned thermal baths of Bagno Vignoni and Bagni San Filippo. This house has earned excellent ratings for its location, cleanliness, and overall experience. This two-bedroom home offers 810 square feet of space and comfortably accommodates four guests. Casa Primavera provides a fully equipped kitchen, a relaxing living room, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
9.0 4 reviews
Pienza
07/25 – 07/28
$214/nighttotal: $642 (3 )
Il Tramonto Di Pienza
2 3
house , Pienza
Pienza Apartment with garden is located in Pienza, Tuscany, offering easy access to the town's historic center and nearby attractions. This 650-square-foot (approximately 60-square-meter) house sleeps nine guests and features a fully equipped kitchen, private garden, free parking, air conditioning, Wi-Fi, and a fireplace.
9.9 213 reviews
Pienza
09/06 – 09/08
$204/nighttotal: $408 (2 )
Agriturismo Chiancianello
1 2
gîte , Pienza
Agriturismo Chiancianello, near Lucciolabella, offers a family-friendly rental in the Val d'Orcia, a 15-20 minute drive from Pienza and other Tuscan towns like Montepulciano and Montalcino. This vacation home boasts a swimming pool, garden, sauna, and parking, plus on-site bike rentals and proximity to hiking trails like the Via Francigena, thermal baths, and a planned biolake (opening 2023).
Pienza
08/13 – 08/17
$5878/nighttotal: $23512 (4 )
Agriturismo La Chiusa Tuscany
18 6
house , Torrita di Siena
La Chiusa is a villa located in the mountains of Torrita di Siena, just a short distance from the Palazzo Borgia and Artemisia Gallery. The surrounding area offers a peaceful escape from the hustle and bustle of city life, allowing you to fully immerse yourself in the tranquility of the Tuscan countryside. This luxurious estate spans 40,000 square feet and can accommodate up to 40 guests. La Chiusa offers a wide range of amenities, including a swimming pool, spa, and garden, as well as activities like mountain biking, horse riding, and wine tasting.
10 2 reviews
Pienza
07/09 – 07/19
$415/nighttotal: $4150 (10 )
Primo Maggio
1 3
house , Castiglione d'Orcia
This Primo Maggio villa in Castiglione d'Orcia is located 3.3 miles from Bagno Vignoni, 11 miles from Bagni San Filippo, and approximately 19 miles from Mount Amiata. This 1940 sq ft villa accommodates up to 15 guests with 1 bedroom and 4 bathrooms, featuring a full kitchen and complimentary WiFi.
9.4 920 reviews
Pienza
07/01 – 07/08
$275/nighttotal: $1925 (7 )
Agriturismo Bonello
1 2
farm , Pienza
Agriturismo Bonello is a historic farmhouse in the Val D'Orcia nature reserve, a short drive from Pienza and Siena. It has excellent user, location, and cleanliness ratings. The farmhouse offers a range of apartments with fully equipped kitchens, accommodating up to 6 guests. It also features an outdoor swimming pool, a restaurant serving authentic Tuscan cuisine, a bar, a fitness center, a sauna, a spa, and room service.
9.0 10 reviews
Pienza
06/19 – 06/21
$294/nighttotal: $588 (2 )
70 M² House ∙ 1 Bedroom ∙ 2 Guests
1 2
house , San Quirico d'Orcia
This Tuscan vacation rental is situated near San Quirico d'Orcia, offering easy access to the Renaissance garden at the Church of Santa Maria Assunta and the town's historic center. This 810-square-foot house features one bedroom, two bathrooms, and sleeps four, complete with a fully equipped kitchen (including a fridge and dishwasher), a garden, parking, and internet access.
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.
9.5 1587 reviews
Pienza
07/02 – 07/03
$316/nightfor 1 night
Agriturismo Il Casalino
2 2
farm , Pienza
Agriturismo Il Casalino, a 19th-century farmhouse, is located just 24 miles from Siena and 29 miles from Arezzo, surrounded by olive groves and vineyards. This farm consistently earns excellent ratings for cleanliness, location, and overall user experience. The farmhouse offers independent apartments with private entrances, providing a comfortable and private stay. Guests can enjoy a range of amenities, including a terrace, garden, and open-plan kitchens, as well as activities like biking and hiking.
9.8 23 reviews
Pienza
10/09 – 10/12
$150/nighttotal: $450 (3 )
18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests
1 2
farm , Pienza
Accommodation for 2 guests with an excellent rating of 98% based on 23 reviews. You will be in Pienza. Services and facilities: a washing machine, a swimming pool and a freeze. This accommodation also has a terrace!
Pienza
10/10 – 10/12
$420/nighttotal: $840 (2 )
Villa Cielo
1 5
house , Trequanda
Villa Cielo, a house in Trequanda, is located 29 miles from Piazza Grande and 15 miles from Bagno Vignoni, offering a peaceful escape in the Tuscan countryside. This 1680 square foot villa accommodates up to 11 guests with 3 bedrooms and 3 bathrooms, featuring a full kitchen with a dishwasher, air conditioning, a swimming pool, and free WiFi and parking.
9.6 5 reviews
Pienza
06/26 – 06/29
$280/nighttotal: $840 (3 )
Agriturismo 'Villa Agriturismo Il Pratone' With Mountain View, Private Pool And Wi-fi
2 4
house , Castiglione d'Orcia
This Castiglione d'Orcia villa, near the Tentennano Fortress (1.1 km) and Piazza delle Sorgenti (4 km), offers a secluded mountain setting with stunning views and easy access to other attractions like Tenuta Sanone and Poggio Grande. This 1,160-square-foot vacation home features three bedrooms, two bathrooms, and sleeps six, boasting a private pool, garden, barbecue grills, a fireplace, and free Wi-Fi.
Best family friendly Pienza villas and beach houses
Among the 8 accommodations in Pienza, here are the 4 best family friendly villas and beach houses
9.7 6 reviews
Pienza
06/17 – 06/22
$156/nighttotal: $780 (5 )
43 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests
1 2
farm , Montepulciano
Farm rental for 4 people with an excellent rating of 97% based on 6 reviews. Your accommodation will be located in Montepulciano. Services and facilities: rooms suitable for events, a washing machine and a swimming pool. Pets are allowed in this accommodation.
9.4 302 reviews
Pienza
12/07 – 12/10
$1504/nighttotal: $4512 (3 )
Palazzo Massaini - Le Scuderie
4 8
farm , Pienza
Palazzo Massaini - Le Scuderie, a Pienza farmhouse stay, is conveniently located 8.1 miles from Montepulciano Terme and 11 miles from Bagno Vignoni, offering easy access to major Tuscan towns. This one-bedroom, one-bathroom rural retreat sleeps two guests and boasts an infinity pool, on-site yoga classes, bicycle rentals, a private terrace, and a complimentary continental breakfast featuring local specialties.
9.2 6 reviews
Pienza
06/26 – 06/29
$271/nighttotal: $813 (3 )
100 M² Villa ∙ 2 Bedrooms ∙ 6 Guests
2 4
house , Castiglione d'Orcia
Villa Agriturismo Il Pratone, located in Castiglione d’Orcia, Tuscany, offers a tranquil escape amidst olive groves, vineyards, and oak forests. This 1,162-square-foot farmhouse features two bedrooms, two bathrooms, a private fenced pool (open May 1st to October 31st), and accommodates up to six guests, complete with Wi-Fi, a fully equipped kitchen, and parking for three vehicles.
Pienza
06/18 – 06/20
$317/nighttotal: $634 (2 )
Cosy Apartment With Pool, A/c, Wifi, Tv, Terrace And Pets Allowed, Close To Montepulciano
2 2
farm , Trequanda
This farm stay is located in the renowned Orcia Valley, 10 miles from Torrita di Siena and 16 miles from Montepulciano, offering scenic hill and lake views. This 1000 square foot agriturismo accommodates up to 4 guests in 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, internet, and access to a shared outdoor pool open from April to November.
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.
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?
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 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?
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?
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?
Maria Gabriella Home & Cottage in Monticchiello, a short distance from Montepulciano Terme (6.3 miles) and Bagno Vignoni (8.1 miles), offers convenient access to Tuscan attractions with Mount Amiata approximately 27 miles away. This cottage provides a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, complimentary Wi-Fi, on-site parking, and scenic garden views, with opportunities for hiking in Monticchiello.
8.9 28 reviews
Pienza
07/13 – 07/15
$102/nighttotal: $204 (2 )
Casella Tarugi
2 2
farm , Pienza
Casella Tarugi, a farm stay in Pienza, Tuscany, is located 9 miles from Bagno Vignoni and 22 miles from Mount Amiata, offering easy access to these Tuscan attractions. This Pienza countryside rental boasts a 270-square-foot floor area, featuring a swimming pool, garden, terrace, free Wi-Fi, and on-site parking, plus bike and car rentals for exploring the area.
9.7 259 reviews
Pienza
07/02 – 07/03
$140/nightfor 1 night
Poggio Al Vento
1 2
house , Castiglione d'Orcia
This Castiglione d'Orcia vacation rental, Poggio Al Vento, is conveniently located 3.5 miles from Bagno Vignoni and 19 miles from Siena's Piazza del Campo. The one-bedroom, one-bathroom house features a fully equipped kitchen, private patio with mountain views, swimming pool, and barbecue facilities; guests can enjoy on-site wine tasting and nearby outdoor play equipment.
Pienza
12/07 – 12/10
$642/nighttotal: $1926 (3 )
150 M² Villa ∙ 4 Bedrooms ∙ 8 Guests
4 8
house , Pienza
This residence is located in a quiet district of Pienza, offering easy access to the town's historic center and its Renaissance architecture, with panoramic views of the Val d'Orcia. This 1610 square foot villa accommodates up to 8 guests with 4 bedrooms, including three upstairs doubles with en-suite bathrooms and a separate ground-floor double with its own shower room and private external access, featuring a fully equipped kitchen, living room with fireplace, and laundry room.
Best Pienza houses with a garden
9.6 215 reviews
Pienza
06/17 – 06/22
$421/nighttotal: $2105 (5 )
Le Checche
1 2
farm , Pienza
Le Checche is a countryside farm located near Pienza, about 35 kilometers from Mount Amiata, 9 kilometers from Bagno Vignoni and 16 kilometers from Bagni San Filippo. The farm offers a swimming pool, a hot tub, a restaurant, a garden, and private parking, along with comfortable accommodations with air conditioning, free Wi-Fi, and private bathrooms.
9.3 77 reviews
Pienza
08/16 – 08/22
$211/nighttotal: $1266 (6 )
Agriturismo I Savelli
1 2
farm , Castiglione d'Orcia
Agriturismo I Savelli, in Castiglione d'Orcia, Tuscany, is conveniently located 3.2 miles from Bagno Vignoni and 4.7 miles from Bagni San Filippo, renowned thermal spring towns, and 12 miles from Mount Amiata, ideal for hiking. This farm stay, built in 1950, offers air-conditioned rooms with private bathrooms, some with kitchens, plus a pool, garden, terrace, free Wi-Fi, and free parking; guests can enjoy stunning garden views and the Tuscan countryside.
9.8 8 reviews
Pienza
06/26 – 06/29
$244/nighttotal: $732 (3 )
Villa Agriturismo Il Pratone
2 4
house , Castiglione d'Orcia
Villa Agriturismo Il Pratone, a pet-friendly Tuscan estate in Castiglione d'Orcia, offers stunning mountain views and easy access to the Tuscan countryside. This 1000-square-foot vacation home features two bedrooms, two bathrooms, a private pool (open May 1st to October 31st, weather permitting), parking for three cars, and can comfortably accommodate up to six guests with amenities including high chairs and baby cots.
9.7 814 reviews
Pienza
06/18 – 06/20
$136/nighttotal: $272 (2 )
Agriturismo Pescaia
1 2
farm , Montepulciano
Agriturismo Pescaia is located in the Tuscan countryside, just 6.2 miles from Chianciano Terme and a 25-minute drive from San Quirico d’Orcia, offering a peaceful escape amidst rolling hills and vineyards. This farm stay receives excellent ratings for its location, cleanliness, and overall experience. Each apartment features a fireplace, a flat-screen TV, a dining area, and a fully equipped kitchenette with oven, offering comfortable and independent living. Enjoy the convenience of free Wi-Fi, a private bathroom with a shower and hairdryer, and a relaxing garden with stunning views.