Pienza holiday homes

We found 1,646 holiday rentals — enter your dates for availability
Select from 32 houses, 40 apartments and other holiday rentals to find the perfect place for your stay in Pienza. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Pienza

Showing deals for:11 Dec - 18 Dec

Living area
Pool
Dining
Outdoor dining
Exceptional
(14 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Montalcino

10% off
NZ$32,526
for 7 nights, 1 villa
NZ$4,647 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Exterior
Outdoor dining
Interior
Pool
Exceptional
(5 reviews)

Villa Curiano - Siena

Monteroni d'Arbia

6% off
NZ$22,629
for 7 nights, 1 villa
NZ$3,233 per night
includes taxes & fees
Villa Curiano - Siena
Outdoor dining
Pool
Pool
Exterior
Exceptional
(14 reviews)

Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,

Castiglione d'Orcia

43% off
NZ$6,510
for 7 nights, 1 villa
NZ$930 per night
includes taxes & fees
Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,
Outdoor dining
Pool
Dining
Exterior
Exceptional
(17 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

9% off
NZ$7,239
for 7 nights, 1 villa
NZ$1,034 per night
includes taxes & fees
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Exterior detail
Pool
Exterior
Outdoor dining
Exceptional
(52 reviews)

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pienza

9% off
NZ$6,700
for 7 nights, 1 villa
NZ$957 per night
includes taxes & fees
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Private kitchen
Private kitchen
Room
Private kitchen
Exceptional
(11 reviews)

"Il Focolare" Superior Apartment in Monticchiello

Pienza

5% off
NZ$1,547
for 7 nights, 1 home
NZ$221 per night
includes taxes & fees
"Il Focolare" Superior Apartment in Monticchiello
Private kitchen
Outdoor dining
Living area
Living area
Exceptional
(5 reviews)

Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

9% off
NZ$3,056
for 7 nights, 1 home
NZ$437 per night
includes taxes & fees
Suite Gioconda - Podere Casa Rossa in Pienza
Living area
Exterior
Outdoor dining
Private kitchen
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
NZ$3,004
for 7 nights, 1 home
NZ$429 per night
includes taxes & fees
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Pool
Property grounds
Property grounds
Exterior
Exceptional
(12 reviews)

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Radicofani

9% off
NZ$4,469
for 7 nights, 1 home
NZ$638 per night
includes taxes & fees
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Living area
Outdoor dining
Bathroom
Room
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

9% off
NZ$3,707
for 7 nights, 1 apartment
NZ$530 per night
includes taxes & fees
Magnificent and Bright 2 BR Apt. with Terrace
Bedroom2
Kitchen with View.
Living room with large sofa bed and dining/working table and smart tv.
Kitchen
Exceptional
(12 reviews)

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Montepulciano

23% off
NZ$1,793
for 7 nights, 1 apartment
NZ$256 per night
includes taxes & fees
Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
Interior
Gorgeous View to wake up to in the mornings!
Interior
Classic Apt. in a Palazzo with modern comforts and classic features
Exceptional
(36 reviews)

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Montepulciano

13% off
NZ$4,828
for 7 nights, 1 apartment
NZ$690 per night
includes taxes & fees
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
  • Peace of mind

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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

Why visit Pienza

  • Historic Charm: Wander through Pienza’s enchanting historic piazza and picturesque streets, rich in culture and heritage.
  • Architectural Splendour: Admire the impressive cathedral and monastery that stand as testaments to the city’s storied past.
  • Scenic Views: Enjoy breathtaking vistas of the surrounding countryside, perfect for a leisurely outdoor escapade.
  • Romantic Atmosphere: Experience the city’s intimate, relaxed vibe ideal for a romantic getaway.
  • Culinary Delights: Savour the local pecorino and immerse in Pienza’s blend of fine food and history.

Top attractions near Pienza

Pienza in Tuscany offers a charming mix of outdoor, romantic, and entertainment experiences. Visitors can explore its historic piazza square, a monastery, and a cathedral, all set against a backdrop of rich culture and scenic city views. Ideal for those seeking outdoor adventures and a taste of local heritage, Pienza invites travellers to immerse themselves in its unique blend of history and beauty, making it a perfect destination for a memorable holiday.

Things to do recommended for couples

Discover the charm of Pienza, Tuscany, perfect for a romantic escape. Enjoy a leisurely stroll through its enchanting streets, savour local delicacies, and immerse yourselves in the history and beauty of the region. Experience a memorable getaway in this picturesque Italian gem.

Things to do recommended for families

Families visiting Pienza can explore its charming streets, savour authentic Tuscan flavours, and enjoy kid-friendly outdoor adventures in the picturesque countryside.

Things to do recommended for groups

Experience the thrill of the Saltalbero Adventure Park, a zipline and ropes course located 24km from Pienza. Embrace the great outdoors with your group as you tackle challenging courses and enjoy the stunning Tuscan scenery together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pienza

Whether you're travelling with a group, as a family, with your pets, or planning an extended stay, be sure to use the appropriate filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pienza with a group: Consider the number of bedrooms required, as well as features like a fully equipped kitchen or an outdoor area for a group get-together. Thankfully, you can filter for all these options and more on Vrbo.
  • Traveling to Pienza with young kids: Traveling with little ones can present its challenges. It is essential to prioritise their comfort and safety by choosing accommodation with suitable facilities, like a private pool, and ensuring there are age-appropriate amenities. It’s also wise to think about staying near family-friendly attractions.
  • Taking your pets with you to Pienza: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pienza: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Pienza

Pienza offers a romantic escape with its charming historical streets and luxurious scenery. Visitors can explore its complete guide to local attractions, savour the famed pecorino, and enjoy a relaxing spa town atmosphere. With captivating outdoor experiences and a friendly, secluded vibe, Pienza is a must-visit destination where every corner tells a story.

  • Montepulciano: Nestled 10km from Pienza, Montepulciano offers a blend of romantic ambience and invigorating outdoor adventures. This charming city invites travellers to revel in a culture-themed journey, with local highlights including a historic piazza square and a picturesque lake. In between visits to these landmarks, you can enjoy therapeutic spa treatments or peruse a vibrant shopping area that reflects the authentic Tuscan lifestyle.
  • Montalcino: Located 16km from Pienza, Montalcino is a destination where romance meets dynamic entertainment and outdoor pursuits. The city is celebrated for its captivating historic sites, soothing hotsprings, and an impressive castle that stands testament to its rich past. Visitors can also indulge in popular activities such as spa treatments, body therapies, or even catch a live performance at a local theatre, immersing themselves in the local culture.
  • San Quirico d'Orcia: Just 6km from Pienza, San Quirico d'Orcia is a delightful escape offering a mix of romantic settings, outdoor leisure, and engaging entertainment. The city boasts a blend of natural hotsprings and historical sites, including a serene lake that enhances its tranquil appeal. Here, travellers can also enjoy spa sessions, body treatments, and even a round of golf, ensuring a well-rounded experience in the heart of Tuscany.

Best time to go to Pienza

If you're planning a trip to Pienza, it's a good idea to check both the weather and property rates. The warmest months are July and August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.4°F (4.1°C)Light RainMostly SunnySlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverage
March45.0°F (7.2°C)Light RainMostly SunnyAverage
April50.9°F (10.5°C)Light RainMostly SunnySlightly High
May57.4°F (14.1°C)Light RainMostly SunnyAverage
June66.7°F (19.3°C)Light RainSunnyAverage
July73.0°F (22.8°C)No Rain (Dry)SunnyAverage
August73.0°F (22.8°C)No Rain (Dry)SunnySlightly High
September64.8°F (18.2°C)Light RainMostly SunnySlightly High
October56.7°F (13.7°C)Light RainMostly SunnyAverage
November48.6°F (9.2°C)Light RainMostly SunnySlightly Low
December42.1°F (5.6°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental. We're here to help you find the perfect place for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's innovative Trip Board offers you a convenient space to plan new adventures, pick up from where you paused, or manage your travel arrangements. You can easily find properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Rustic Pienza will entice you

The area's churches and wineries are just some of the reasons to come on holiday to Pienza. This scenic city has many special qualities. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Pienza

Do you want to find attractions to visit while you're in town? Venture out of your holiday home and check out everything that makes Pienza a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Consorzio del Vino Nobile di Montepulciano (5.3 mi / 8.5 km)
  • Piscine Termali Theia (7 mi / 11.2 km)
  • Terme di Chianciano (7.4 mi / 11.9 km)
  • Tenuta Greppo Franco Biondi Santi (9.2 mi / 14.8 km)
  • Baths of San Filippo (10.2 mi / 16.5 km)
  • Castiglion del Bosco Winery (13.2 mi / 21.3 km)

Exploring the natural landscape of Pienza

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Pienza is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Historic Centre of Pienza (0.1 mi / 0.1 km)
  • La Foce (6.2 mi / 10 km)
  • Terme di Montepulciano Spa (6.2 mi / 10 km)
  • Piscine Termali Theia (7 mi / 11.2 km)
  • Val di Chiana (7.1 mi / 11.4 km)
  • Garden of Daniel Spoerri (11.9 mi / 19.2 km)

Frequently asked questions

What is the best area to stay in Pienza when booking a holiday rental?
When considering a holiday rental in Pienza, Tuscany, the historic centre is the best area to stay. This charming neighbourhood is renowned for its stunning Renaissance architecture and picturesque streets, making it an ideal base for exploring the town's rich history. Within the historic centre, visitors can easily access great attractions such as the Palazzo Piccolomini, with its beautiful gardens offering breathtaking views of the surrounding Val d'Orcia countryside, and the stunning Cathedral of Pienza, a masterpiece of Renaissance design.The area boasts a variety of properties, ranging from quaint apartments to elegant villas, providing something for every preference and budget. Staying in this central location allows for easy strolls to local shops, cafes, and restaurants, where you can indulge in the region's famous pecorino cheese and delightful Tuscan cuisine. Additionally, the nearby countryside offers opportunities for scenic walks and bike rides, showcasing the beautiful rolling hills and vineyards that define this part of Tuscany.
Where are the best areas for renting a beach house in Pienza?
For renting a beach house in Pienza, the nearby coastal area of Castiglione della Pescaia is a fantastic option. This charming seaside town along the Tuscan coast offers a selection of beach houses that provide easy access to beautiful sandy beaches and crystal-clear waters. Many of these properties come equipped with amenities such as private terraces, outdoor dining areas, and fully equipped kitchens, making them great for families or groups looking to enjoy a relaxing beach holiday.Just a short drive away from Pienza, you can also explore the stunning beaches at Punta Ala, where holiday rentals often feature modern furnishings, swimming pools, and proximity to local shops and restaurants. The area is known for its elegant beach clubs and vibrant seaside atmosphere, ensuring you have everything you need at hand for a delightful stay.Additionally, the natural beauty of the Maremma region surrounding Pienza offers opportunities for outdoor activities, from hiking in the nearby hills to exploring the picturesque countryside. Rentals in this area frequently boast amenities like gardens, barbecues, and even access to local vineyards, allowing guests to immerse themselves in the delightful Tuscan lifestyle.
What is the most popular type of holiday rental accomodation in Pienza?
In Pienza, apartments are the most popular type of holiday rental, with approximately 188 available in charming locations throughout the town. These apartments often feature traditional Tuscan decor, fully equipped kitchens, and spacious living areas, allowing guests to immerse themselves in the local culture while enjoying the comforts of home. Many also come with balconies or terraces that provide stunning views of the surrounding countryside.Villas follow closely behind, with around 164 options offering more luxurious accommodations. These villas typically provide multiple bedrooms, private gardens, and swimming pools, making them ideal for larger groups or families seeking a more upscale experience. Additionally, there are about 92 holiday houses and several cottages that provide a quaint and rustic feel, great for those wanting a peaceful retreat in the heart of Tuscany.
Are there any family house rentals in Pienza?
In Pienza, Tuscany, there is a great selection of family-friendly house rentals, with around 64 options available. This charming town, known for its stunning Renaissance architecture and picturesque landscapes, offers a variety of accommodations suitable for families. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play and adults can relax while enjoying the beautiful Tuscan countryside.Nearby attractions include the iconic Pienza Cathedral and the scenic Val d'Orcia, superb for family outings and exploration. Visitors can also discover local markets where traditional Tuscan delicacies are sold, providing a delightful experience for all ages.
Can I rent a holiday home with a pool or hot tub in Pienza?
In Pienza, Tuscany, there are numerous holiday homes available for rent that feature pools and hot tubs, with around 69 options to choose from. This picturesque town, famed for its Renaissance architecture and stunning views of the Val d'Orcia, offers a delightful escape for travellers. Many of the rental properties come equipped with private pools, ideal for soaking up the Tuscan sun, as well as hot tubs for ultimate relaxation after a day of exploring.Travellers can expect amenities such as spacious outdoor terraces, well-appointed kitchens, and comfortable living areas, making them superb for families or groups. Additionally, some properties may include outdoor dining areas with barbecues, allowing guests to enjoy al fresco meals amidst the beautiful landscape.
Are there pet-friendly house rentals in Pienza?
In Pienza, there are several pet-friendly house rentals available, offering a charming base for exploring this beautiful Tuscan town. Many of these properties come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The historic centre of Pienza is a UNESCO World Heritage Site and provides a picturesque backdrop for pet owners, with its lovely streets and stunning views of the surrounding countryside. Nearby, the Val d'Orcia region offers plenty of opportunities for outdoor activities, including scenic walks and vineyard visits, where pets are often welcome.Additionally, the local area is dotted with quaint cafes and restaurants that may accommodate pets, enhancing the overall experience for travellers with furry companions.
Are there any remote work holiday rentals in Pienza?
In Pienza, Tuscany, there are numerous remote work-friendly holiday rentals available, with around 400 options to choose from. This enchanting town, known for its stunning Renaissance architecture and picturesque landscapes, is an ideal setting for those looking to blend work and leisure. Many properties come equipped with essential amenities for remote work, including free Wi-Fi in rooms and public areas, dedicated laptop workspaces, and comfortable living spaces that allow for a productive environment.The charming streets of Pienza offer not only a serene atmosphere but also the allure of local attractions such as the Palazzo Piccolomini and the beautiful Val d'Orcia, making it easy to take breaks and explore the surrounding countryside. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Pienza?
In Pienza, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also offer onsite parking, which is a convenient feature for those exploring the beautiful Tuscany region by car. For added comfort, numerous rentals come with fireplaces, superb for cosy evenings after a day of sightseeing. Additionally, some accommodations are pet-friendly, suiting travellers who wish to bring their furry companions along. Lastly, amenities such as coffee and tea makers are commonly found, providing a nice touch for guests to enjoy their morning brews while taking in the stunning views of the surrounding countryside.
When is the best time to visit Pienza for a holiday rental?
The best time to visit Pienza for a holiday rental is in September, when the region begins to transition from the bustling summer peak. This month offers a superb blend of pleasant weather and fewer crowds, allowing for a more relaxed exploration of this beautiful Tuscan town. With average temperatures ranging from 15 to 25 degrees Celsius, September provides ideal conditions for outdoor activities such as leisurely walks through the scenic vineyards and olive groves that characterise the area.During the peak season from July to September, Pienza attracts a vibrant mix of tourists eager to experience its rich history, stunning architecture, and delicious cuisine. While July is the busiest month, September strikes a harmonious balance, as visitors can still enjoy local festivals and markets without the overwhelming hustle and bustle.For those seeking a more budget-friendly option, visiting in January can be quite appealing. Although this is the low season, it offers a unique opportunity to experience Pienza's charm in a quieter atmosphere. This time of year allows for intimate explorations of the town's quaint streets and the chance to savour winter delicacies at local trattorias.Ultimately, the best time to book a holiday rental in Pienza hinges on your preferences for vibrant summer energy or the tranquillity of the winter months.
What are the top attractions in Pienza?
In Pienza, visitors can take part in the enchanting Renaissance architecture and picturesque landscapes that define this charming town. The Piazza Pio II is a central attraction, featuring the stunning Pienza Cathedral and the Palazzo Piccolomini, where you can enjoy breathtaking views of the Val d'Orcia.Wander through the quaint streets lined with local shops selling artisanal cheese, particularly the famous pecorino, offering a true taste of the region. Nearby, the beautiful gardens of the Palazzo Piccolomini provide a serene spot for relaxation and scenic vistas.For those interested in art and history, the town is also close to the historic sites of Montepulciano and Montalcino, where you can explore additional cultural treasures and sample exquisite wines.
Are all fees included in the Pienza holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pienza holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Pienza with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pienza holiday homes?
You can find great discounts on holiday homes in Pienza on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pienza holiday home booking on Bookabach?
To find Pienza holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Pienza?
A long-stay holiday home in Pienza is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pienza holiday home?
Book your Pienza holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pienza?
Prices for holiday homes in Pienza vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Pienza to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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