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Pienza villas
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12 Villa rentals in Pienza

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 Il Casalino - Pienza
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.
18 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Pienza
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!
Villa Cielo - Pienza
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.
Agriturismo 'Villa Agriturismo Il Pratone' With Mountain View, Private Pool And Wi-fi - Pienza
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

43 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Pienza
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.
Palazzo Massaini - Le Scuderie - Pienza
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.
100 M² Villa ∙ 2 Bedrooms ∙ 6 Guests - Pienza
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.
Cosy Apartment With Pool, A/c, Wifi, Tv, Terrace And Pets Allowed, Close To Montepulciano - Pienza
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.
  • 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.

Destinations nearby

Best Pienza houses with parking

Maria Gabriella Home & Cottage - Pienza
Pienza
07/19 – 07/23
$371/nighttotal: $1484 (4 )

Maria Gabriella Home & Cottage

1 2
house , 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.
Casella Tarugi - Pienza
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.
Poggio Al Vento - Pienza
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.
150 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
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

Le Checche - Pienza
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.
Agriturismo I Savelli - Pienza
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.
Villa Agriturismo Il Pratone - Pienza
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.
Agriturismo Pescaia - Pienza
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.
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