San Gimignano holiday rentals

We found 2,774 holiday rentals — enter your dates for availability
Select from 53 houses, 119 apartments and other holiday rentals to find the perfect place for your stay in San Gimignano. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – San Gimignano

Showing deals for:20 Nov - 27 Nov

Interior
Interior
Living area
Pool
Exceptional
(42 reviews)

VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.

Certaldo

8% off
AU$10,571
for 7 nights, 1 villa
AU$1,510 per night
includes taxes & fees
VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.
Exterior detail
Interior
Dining
Room
Exceptional
(64 reviews)

Locanda del podestà: 17th century mansion in Chianti

Montespertoli

8% off
AU$2,505
for 7 nights, 1 villa
AU$358 per night
includes taxes & fees
Locanda del podestà: 17th century mansion in Chianti
Property grounds
Pool
Exterior
Outdoor dining
Exceptional
(10 reviews)

Tuscany holiday home for 2-6, private pool, fenced garden, scenic terrace view

Volterra

6% off
AU$2,077
for 7 nights, 1 home
AU$297 per night
includes taxes & fees
Tuscany holiday home for 2-6, private pool, fenced garden, scenic terrace view
Exterior detail
Outdoor dining
Interior
Dining
Exceptional
(36 reviews)

GARDEN HOUSE

San Gimignano

7% off
AU$1,870
for 7 nights, 1 apartment
AU$267 per night
includes taxes & fees
GARDEN HOUSE
Exterior
Outdoor dining
Private kitchen
Pool
Exceptional
(57 reviews)

La Casetta del Borgo San Gimignano, relax nature swimming pool, STARLINK powered

Gambassi Terme

8% off
AU$1,202
for 7 nights, 1 apartment
AU$172 per night
includes taxes & fees
La Casetta del Borgo San Gimignano, relax nature swimming pool, STARLINK powered
Pool
Property grounds
Property grounds
Interior
Exceptional
(81 reviews)

Villa with large garden in the Chianti hills

Castellina in Chianti

9% off
AU$908
for 7 nights, 1 home
AU$130 per night
includes taxes & fees
Villa with large garden in the Chianti hills
Interior
Exterior detail
Property grounds
Terrace/patio
Wonderful
(11 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
AU$1,970
for 7 nights, 1 home
AU$281 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena
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Why visit San Gimignano

  • Historic architecture: Marvel at the iconic medieval towers and charming piazzas that define San Gimignano's skyline.
  • Cultural heritage: Explore historic churches and intriguing museums that showcase the city's rich artistic past.
  • Scenic vistas: Enjoy breathtaking views of the Tuscan countryside from various vantage points throughout the city.
  • Local cuisine: Savor authentic Tuscan dishes and local wines in quaint restaurants and outdoor eateries.
  • Charming atmosphere: Wander the enchanting streets, immersing yourself in the romantic ambiance of this medieval gem.

Popular types of accommodation in San Gimignano

You have decided on a trip to San Gimignano, Tuscany, Italy, and now comes the fun part – choosing your accommodation. Enjoy friendly, cosy guesthouses, apartments, private holiday homes, and villas, all offering a warm welcome. Discover local attractions like medieval towers and charming piazzas, while experiencing pet-friendly options and a range of friendly holiday rentals that cater to every traveller’s needs.

  • Apartments: A favoured choice among visitors, apartments offer a blend of comfort and convenience, ideal for experiencing local life.
  • Private Holiday Homes: These homes provide a home-away-from-home atmosphere, perfect for families or groups wanting extra space.
  • Villas: For those seeking luxury, villas provide spacious living and stunning views, ensuring a memorable stay.
  • Caravan Parks: A unique option, caravan parks allow for a more adventurous experience amidst nature.
  • Cottages: Charming and cosy, cottages are perfect for a quaint getaway, often nestled in picturesque settings.**

Top attractions in San Gimignano

Explore the enchanting city of San Gimignano in Tuscany, Italy, where historic churches, majestic castles, and intriguing museums offer a blend of culture and romance. Stroll through streets steeped in history, savour outdoor experiences, and immerse yourself in a city that promises captivating sightseeing and memorable tours. Discover the charm of this captivating destination and its rich heritage without venturing beyond its ancient walls.

  • San Gimignano Communal Palace: Experience the rich civic history and cultural charm of this historic building, where centuries of governance are evident in its distinctive architecture.
  • Medieval Criminal and Torture Museum: Delve into the darker side of medieval justice with exhibits that illuminate the grim realities of the past, set within an atmospheric venue.
  • Torre Grossa: Climb this iconic tower for breathtaking views over San Gimignano, appreciating its storied past and the panoramic vistas of the Tuscan landscape.

Things to do recommended for couples

Immerse yourselves in the charm of San Gimignano with a leisurely stroll through its medieval streets, hand in hand. Enjoy a wine tasting at a local vineyard, savouring the exquisite Vernaccia, followed by a romantic sunset view from the Torre Grossa. Truly a memorable experience for couples.

Things to do recommended for families

Families in San Gimignano enjoy a day exploring the medieval towers, savour local gelato, and wander the charming streets. A fun, immersive experience awaits with engaging local crafts and picturesque views suitable for all ages.

Things to do recommended for groups

Explore the medieval charm of San Gimignano with a guided walking tour, indulge in a cooking class to master local Tuscan dishes, or enjoy a wine tasting at a nearby vineyard, sampling the renowned Vernaccia di San Gimignano. Each activity promises a delightful cultural immersion for your group.

*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 San Gimignano

Whether you're journeying with a group, as a family, accompanied by your pets, or seeking extended stays, ensure you filter according to your priorities. Here are some Stayz booking tips for you.

  • Traveling to San Gimignano with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Stayz.
  • Traveling to San Gimignano with young kids: Traveling with young children can be challenging. You must prioritise their comfort and safety, ensuring the availability of age-appropriate facilities, such as a private swimming pool. It is also wise to consider how near you are to attractions that are suitable for families.
  • Taking your pets with you to San Gimignano: For many families, a trip isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Stayz 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 San Gimignano: If you're seeking holiday rentals with special offers for extended stays of a month or more, you've come to the right place. By applying the appropriate filters, you can effortlessly locate and secure savings on monthly rentals. You might also consider adding options such as a parking space, a well-appointed kitchen, or a private pool to your search criteria.

Where to stay in San Gimignano

Discover the charm of San Gimignano, a historic Tuscan gem renowned for its medieval towers and scenic vistas. Wander ancient streets, admire timeless architecture and quaint piazzas, and indulge in the local culinary delights. Experience a blend of romance, entertainment, and outdoor adventures in an atmosphere steeped in history and luxury. San Gimignano offers a truly unforgettable escape into the heart of Tuscany.

  • San Gimignano City Centre: Nestled in the heart of San Gimignano, the City Centre offers a rich tapestry of cultural and romantic experiences. Visitors can immerse themselves in the local history by exploring ancient landmarks, museums and a picturesque piazza square. The area is celebrated for its outdoor activities and theatre performances, creating an inviting atmosphere for those seeking both relaxation and cultural enrichment. The blend of historic charm and contemporary leisure ensures a memorable travel experience.
  • Ulignano: Set in the scenic surroundings of San Gimignano, Ulignano is a quaint village ideal for travellers seeking a romantic retreat and outdoor adventures. Here, the allure of nature meets history, with nearby lakes, historic sites and a castle that tell tales of the past. The village offers a slower pace of life, perfect for leisurely walks and theatre outings, making it a delightful escape for those looking to savour both tranquillity and beauty.
  • Castel San Gimignano: This charming village is steeped in history and culture, offering a blend of city-themed and romantic experiences. Wander through its cobbled streets and discover hidden piazza squares, ancient historic sites and art galleries that showcase the artistic heritage of the region. Tours and walking excursions provide an engaging way to explore the local landmarks, ensuring that every visit is rich in discovery and historical intrigue.

Best time to go to San Gimignano

If you're planning a trip to San Gimignano, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and November, while off-peak times, like January to February and October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
February43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low
March48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
April54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
May61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
June70.7°F (21.5°C)Light RainSunnySlightly HighSlightly High
July76.3°F (24.6°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.9°F (24.4°C)No Rain (Dry)SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
October59.0°F (15.0°C)Light RainMostly SunnySlightly LowAverage
November50.4°F (10.2°C)Light RainMostly SunnySlightly HighSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnyAverageAverage

Booking with Stayz is simple

Looking to cut costs on your next break? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board offers a handy place to set up new journeys, continue from where you last stopped, or review and organise your plans. You can see properties you have either saved or booked neatly arranged under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Head to the historical city of San Gimignano

Come and experience San Gimignano and its history, museums and cathedral. This walkable city is known for its cafes, wineries and monuments. 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 and around San Gimignano

Are you searching for attractions to see during your stay? Venture out of your holiday home and experience everything that makes San Gimignano a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Sovestro in Poggio Winery (0.9 mi / 1.5 km)
  • Tenuta Torciano Winery (3.5 mi / 5.6 km)
  • Agricola Tamburini Emanuela (7 mi / 11.2 km)
  • Castello di Monsanto (7.5 mi / 12.1 km)
  • Castello della Paneretta (8 mi / 12.9 km)
  • Casa Sola - Chianti Winery (10 mi / 16.1 km)

Exploring the natural landscape of San Gimignano

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, San Gimignano is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (5.3 mi / 8.6 km)
  • Alta Val d'Elsa River Park (7.1 mi / 11.4 km)
  • Chianti Sculpture Park (17.7 mi / 28.5 km)
  • Val di Merse (22.1 mi / 35.6 km)
  • Arno River (23.3 mi / 37.5 km)
  • Le Caldane Thermal Baths (7 mi / 11.3 km)

Travelling to and around San Gimignano

The nearest airport is in Peretola Airport (FLR), located 24.4 mi (39.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in San Gimignano when booking a holiday rental?
When considering a holiday rental in San Gimignano, a charming medieval town in Tuscany, the historical centre is the best area to stay. This picturesque neighbourhood is renowned for its stunning towers and well-preserved architecture, offering visitors an authentic glimpse into the past. The area boasts a range of holiday properties, from quaint apartments to more luxurious options, allowing for a delightful stay amidst the town's captivating atmosphere.While in the historical centre, you can easily explore top attractions such as the Collegiate Church of Santa Maria Assunta, which showcases incredible frescoes and a stunning interior, and the Piazza della Cisterna, a lovely square great for enjoying a gelato while soaking in the vibrant surroundings.
Where are the best areas for renting a beach house in San Gimignano?
For renting a beach house near San Gimignano, it's important to note that the town itself is situated inland and is not directly on the coast. However, there are lovely areas along the Tuscan coastline that are within a reasonable drive, particularly towards the seaside towns of San Vincenzo and Castiglione della Pescaia.In the San Vincenzo area, visitors can find beach houses that offer stunning views of the Tyrrhenian Sea, often featuring amenities such as private terraces, outdoor dining areas, and easy access to sandy beaches. Many properties in this region come equipped with modern kitchens, making it convenient for families or groups to prepare meals and enjoy al fresco dining while soaking in the coastal atmosphere.If you venture further south to Castiglione della Pescaia, you'll discover charming villas and beachfront apartments that cater to holidaymakers. Here, amenities frequently include private pools, garden spaces, and proximity to local shops and restaurants, allowing for a comfortable and enjoyable stay. The beaches are typically well-maintained and ideal for sunbathing or enjoying water sports.While San Gimignano itself is renowned for its medieval architecture and stunning hilltop views, the nearby coastal areas offer the great complement for travellers seeking both cultural experiences and beach relaxation.
What is the most popular type of holiday rental accomodation in San Gimignano?
In San Gimignano, apartments are the most popular type of holiday rental, with approximately 756 available throughout the charming medieval town. These apartments typically offer amenities such as fully equipped kitchens, comfortable living areas, and often stunning views of the surrounding Tuscan countryside. Many are located near key attractions like the iconic towers, the Collegiata di Santa Maria Assunta, and local vineyards, making them ideal for exploring the rich history and culture of the area.In addition to apartments, there are around 256 villas and 240 holiday houses, which cater to those seeking more space and privacy. These properties often feature multiple bedrooms, private gardens, and outdoor patios, allowing guests to enjoy the beautiful Tuscan weather. For a more rustic experience, there are also a small number of cottages and several campsites available, providing a range of options for different preferences and group sizes.
Are there any family house rentals in San Gimignano?
In San Gimignano, Tuscany, there is a wide selection of family-friendly holiday rentals, with around 171 available. This charming medieval town is renowned for its stunning towers and picturesque landscapes, making it a wonderful choice for families. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces for children to play and enjoy the Tuscan sun.Visitors can find accommodations in various neighbourhoods, each offering unique access to local attractions. For instance, homes located near the historic centre allow easy exploration of the town's famous squares, like Piazza della Cisterna, as well as art galleries and delightful gelaterias. Additionally, properties situated on the outskirts often come with beautiful gardens and views of the rolling hills, providing a peaceful retreat after a day of sightseeing.Family-oriented amenities such as Wi-Fi, air conditioning, and sometimes even swimming pools can be expected, ensuring a comfortable stay.
Can I rent a holiday home with a pool or hot tub in San Gimignano?
In San Gimignano, there are plenty of holiday homes available for rent that come equipped with pools or hot tubs, with around 204 options to choose from. This picturesque town in Tuscany is renowned for its medieval towers and beautiful landscapes, making it a delightful destination for travellers seeking relaxation and adventure.You can find these properties scattered throughout the surrounding countryside and in the town itself, often featuring stunning views of the vineyards and rolling hills. Many rentals have private pools, outdoor terraces for al fresco dining, and hot tubs, providing a luxurious setting to unwind after exploring the area's rich history and cultural sites.Expect amenities such as fully equipped kitchens, spacious living areas, and charming outdoor spaces, ideal for families or groups wanting to enjoy the tranquil Tuscan atmosphere. Additionally, the proximity to local wineries and traditional trattorias enhances the experience, allowing guests to indulge in the region's culinary delights. Find your rental in San Gimignano with a pool or a hot tub.
Are there pet-friendly house rentals in San Gimignano?
In San Gimignano, there are numerous pet-friendly house rentals available, with around 155 options to choose from. This enchanting medieval town in Tuscany offers a variety of holiday homes that cater to travellers with pets. Many of these rentals feature spacious gardens or outdoor terraces, providing ample space for pets to roam and play. Inside, guests can expect comfortable amenities such as well-equipped kitchens, Wi-Fi, and cosy living areas, superb for relaxing after a day of exploring the town's historic attractions.The area is rich in cultural heritage, with the iconic towers of San Gimignano and charming cobblestone streets to wander through. Additionally, nearby parks and countryside trails offer excellent opportunities for walking and enjoying nature with pets. The surrounding Tuscan landscape, dotted with vineyards and olive groves, is ideal for leisurely strolls, making it a delightful destination for both pet owners and their furry companions.
Are there any remote work holiday rentals in San Gimignano?
In San Gimignano, Tuscany, there are numerous options for remote work holiday rentals, with around 1,060 properties available. This picturesque medieval town offers a unique blend of history and modern amenities, making it an excellent choice for those looking to work remotely. Many of the rentals come equipped with reliable Wi-Fi, ensuring a seamless connection for virtual meetings or work tasks.Travellers can expect a variety of accommodations, from charming apartments in the town's historic centre to spacious villas set amidst the stunning Tuscan countryside. Common amenities often include comfortable workspaces, fully equipped kitchens for self-catering, and outdoor areas where one can relax after a day of work. The proximity to local attractions, such as the iconic towers and beautiful vineyards, adds to the appeal of working from this enchanting destination. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in San Gimignano?
In San Gimignano, holiday rentals often feature a variety of popular amenities that enhance the guest experience. Most properties come equipped with a kitchen, allowing visitors to prepare their own meals and enjoy the local produce. Onsite parking is commonly available, making it convenient for those travelling by car. Many rentals also permit pets, accommodating furry companions during the stay. Additionally, you can expect amenities like coffee and tea makers for those essential morning brews, as well as provisions for service animals, ensuring a comfortable stay for all guests.
When is the best time to visit San Gimignano for a holiday rental?
The best time to visit San Gimignano for a holiday rental is during the enchanting month of November. This period marks the peak season, running from November to January, when the charming medieval town is adorned with festive decorations, and the atmosphere is filled with warmth and celebration.With mild temperatures ranging from 5 to 15 degrees Celsius, November provides a comfortable climate for outdoor activities and sightseeing. You can explore the town's iconic towers and winding streets, and enjoy the stunning Tuscan countryside, all while indulging in local wine tastings and delicious cuisine.If you're looking for a more budget-friendly option, consider visiting in October. This month is less crowded but still offers delightful experiences, such as the grape harvest festival, where you can immerse yourself in the local culture and enjoy the vibrant autumn colours.Ultimately, your choice will depend on whether you prefer the bustling energy of the peak season in November or the quieter charm of October, where you can enjoy the beauty of San Gimignano at a more relaxed pace.
What are the top attractions in San Gimignano?
In San Gimignano, visitors can engage in a rich tapestry of history and culture. The town is famed for its medieval towers, with the Torre Grossa being the tallest and offering stunning views of the surrounding countryside. The historic centre, a UNESCO World Heritage Site, is filled with charming cobblestone streets and ancient buildings that showcase the town's architectural heritage.The Piazza della Cisterna is a central gathering place, surrounded by delightful cafés and shops, making it a great spot to relax and enjoy local delicacies such as the renowned Vernaccia di San Gimignano wine. Nearby, the Collegiate Church of Santa Maria Assunta features impressive frescoes that captivate art enthusiasts.For those interested in local history, the San Gimignano 1300 Museum provides a fascinating glimpse into the town's past through intricate models and exhibits.
Are all fees included in the San Gimignano holiday homes prices shown on Stayz?
Stayz 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 San Gimignano holiday homes with parking?
Stayz offers a wide selection of holiday homes in San Gimignano 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 San Gimignano holiday homes?
You can find great discounts on holiday homes in San Gimignano on Stayz, 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 San Gimignano holiday home booking on Stayz?
To find San Gimignano holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in San Gimignano?
A long-stay holiday home in San Gimignano 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 Stayz?
Stayz'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 San Gimignano holiday home?
Book your San Gimignano 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in San Gimignano?
Prices for holiday homes in San Gimignano 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. Stayz offers something for every taste and budget, from affordable homes in San Gimignano to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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