Radda in Chianti holiday lettings

We found 3,013 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Radda in Chianti that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. At the end of the day, 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 – Radda in Chianti

Showing deals for:16 Oct - 23 Oct

Image gallery for Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Villa Petrolo garden overview & pool
10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Bucine

24% off
Price is £13,259
for 7 nights, 1 home
£1,894 per night
includes taxes & fees
Exclusive Villa 18th century, with pool. Fine winery in Chianti central Tuscany

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Radda in Chianti

  • Charming medieval architecture: Radda in Chianti boasts picturesque streets lined with historic buildings that reflect its rich cultural heritage.
  • Stunning vineyards: The surrounding vineyards offer splendid views and opportunities for leisurely walks and outdoor adventures.
  • Local wine heritage: Delight in exquisite Chianti wines with tours that immerse you in the region's celebrated wine culture.
  • Enchanting piazzas: Vibrant public squares provide a perfect setting for relaxation, where you can savour local cuisine and mingle with friendly locals.
  • Serene atmosphere: The tranquil environment of Radda in Chianti makes it an ideal destination for romantic getaways and rejuvenating retreats.

Popular types of accommodation in Radda in Chianti

Radda in Chianti, nestled in the heart of Tuscany, offers an idyllic escape with its charming streets and stunning landscapes. Visitors can choose from an array of vacation rentals, including elegant apartments, beautiful villas, and houses that exude rustic charm. Experience the warmth of a patrician villa or indulge in a special stay surrounded by vineyards and rolling hills. Discover the rich history and breathtaking views that make Radda in Chianti a perfect destination for memorable holidays.

  • Apartments: The most sought-after option in Radda in Chianti, offering cosy and convenient living spaces for visitors.
  • Villas: Luxurious and spacious properties, ideal for those looking for an upscale experience amidst stunning landscapes.
  • Houses: Charming residences that provide a home-like atmosphere, perfect for families or groups.
  • Caravan Parks: A unique choice for adventurous travellers seeking a blend of nature and comfort.
  • Cottages: Quaint and rustic lodgings that embody the traditional Tuscan charm, perfect for a romantic getaway.**

Top attractions in and around Radda in Chianti

Radda in Chianti, nestled in the heart of Tuscany, offers a charming escape for romantic getaways and outdoor adventures. Discover its historic churches, enchanting castles, and vibrant piazzas that embody the region's rich culture. Enjoy delightful Chianti tours and immerse yourself in the local wine heritage, making your visit truly memorable. Whether you're seeking a serene retreat or an entertaining experience, Radda in Chianti promises captivating sights and experiences for every traveller.

  • Castello di Albola: A stunning castle nestled in the picturesque hills of Radda in Chianti, offering a romantic atmosphere and rich cultural heritage. Explore its vineyards and learn about traditional winemaking.
  • Piazza del Campo: Though located 19km away, this historic square is renowned for its medieval architecture and vibrant atmosphere, perfect for soaking up local culture.
  • Fortezza Medicea: Also 19km distant, this imposing fortress reflects the region's historical significance, providing insight into Tuscan history and stunning views.

Things to do recommended for couples

Ready for a romantic escape in Radda in Chianti? Savour a candlelit dinner at a local trattoria, explore the enchanting vineyards on a leisurely bike ride, and indulge in a wine tasting tour, all while surrounded by breathtaking Tuscan landscapes.

Things to do recommended for families

Your family will delight in exploring the charming medieval streets of Radda in Chianti, visiting local vineyards for family-friendly tours, and enjoying outdoor activities like cycling through the picturesque countryside. Don’t miss the chance to savour delicious gelato from local shops.

Things to do recommended for groups

Experience thrills at Saltalbero Adventure Park, a zipline and ropes course located 27km from Radda in Chianti. Enjoy the adventure and outdoor vibes with your group as you navigate through the treetops and embrace the beautiful Tuscan landscape.

*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 Radda in Chianti

When travelling with a group, family, or pets, or if you're considering extended stays, it's important to apply the appropriate filters to suit your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Radda in Chianti with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can apply filters for all of these options and more on Vrbo.
  • Traveling to Radda in Chianti with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Radda in Chianti: For many, a family holiday isn't truly complete without their furry companion. If that resonates with you, take a look at 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 Radda in Chianti: If you’re in search of holiday rentals that offer discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and benefit from savings on monthly rentals. We also recommend considering options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Radda in Chianti

Radda in Chianti, nestled in the heart of Tuscany, offers a romantic escape with its picturesque landscapes and charming medieval architecture. Stroll through the narrow streets, where friendly locals welcome you to enjoy local wines and exquisite cuisine. Explore the stunning vineyards surrounding the city, ideal for outdoor adventures or leisurely walks. With its serene atmosphere and rich history, Radda in Chianti promises an unforgettable experience for those seeking relaxation and cultural immersion.

  • Chianti Region: The picturesque Chianti Region is located approximately 5km from Radda in Chianti, renowned for its romantic charm and outdoor pursuits. This enchanting area offers a wealth of entertainment options, making it a perfect getaway for those seeking relaxation and adventure. Visitors can indulge in luxurious spa treatments and body therapies while surrounded by stunning landscapes. The region is dotted with historic landmarks, including ancient castles and monuments, allowing travellers to immerse themselves in the rich cultural heritage of Tuscany. The rolling hills and vineyards provide a breathtaking backdrop for leisurely strolls and wine tastings.
  • Villa: Nestled in the vicinity of Radda in Chianti, the quaint village of Villa is a treasure trove for those seeking a romantic and outdoor experience. With an array of guided tours available, visitors can explore the area's captivating history and stunning landscapes. The village boasts remarkable attractions, such as historic sites and a charming botanical garden, perfect for leisurely afternoons. Villa's serene atmosphere and welcoming community create an ideal setting for couples and families alike, offering a delightful escape into the heart of Tuscany.
  • Volpaia: The charming village of Volpaia is also located near Radda in Chianti and is celebrated for its romantic ambiance and outdoor activities. Travellers seeking entertainment can enjoy thrilling rides on the cable car or funicular, while those wishing to unwind can indulge in spa experiences that rejuvenate the senses. Volpaia is rich in history, with notable landmarks including a striking monument and an ancient castle. The stunning vistas and vibrant local culture make it a must-visit destination for anyone exploring the Chianti region.

Best time to go to Radda in Chianti

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January40.8°F (4.9°C)Light RainMostly SunnySlightly LowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to make your next holiday more affordable? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area for you to plan new getaways, refine your existing arrangements, or manage your bookings effectively. The properties you have saved or reserved are neatly categorised into Potential, Upcoming, or Current Trips. To delve into your Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Radda in Chianti

The area's wineries and churches are just some of the reasons to come on holiday to Radda in Chianti. This scenic and romantic city is well known for its local tours, coffee shops and spas. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Radda in Chianti

Are you searching for attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Radda in Chianti a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Castello di Radda Winery (0.7 mi / 1.2 km)
  • Borgo di Vescine - Tenute di Castelvecchi (2.2 mi / 3.5 km)
  • Castello di Albola (2.8 mi / 4.5 km)
  • Badia a Coltibuono (4 mi / 6.4 km)
  • Il Molino di Grace Winery (4.1 mi / 6.7 km)
  • Buondonno Winery (5.6 mi / 9.1 km)

Exploring the natural landscape of Radda in Chianti

Whether you're looking for fun outdoor activities or just want to take in the scenery, Radda in Chianti is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Chianti Sculpture Park (6.5 mi / 10.4 km)
  • Alta Val d'Elsa River Park (13.7 mi / 22.1 km)
  • Terme Antica Querciolaia (17.8 mi / 28.7 km)
  • Arno River (20.1 mi / 32.4 km)
  • Val di Merse (22.6 mi / 36.4 km)
  • Area Naturale Protetta di Interesse Locale Arboreto Monumentale di Moncioni (6.9 mi / 11.1 km)

How to get to and around Radda in Chianti

The nearest airport is in Peretola Airport (FLR), located 23.4 mi (37.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Radda In Chianti when booking a holiday rental?
When considering a holiday rental in Radda In Chianti, the historic centre is an excellent choice for its charming atmosphere and accessibility to local attractions. This area is characterised by its picturesque medieval architecture and offers a variety of properties, from cosy apartments to elegant villas. Staying here allows you to immerse yourself in the local culture, with easy access to delightful shops and traditional restaurants serving regional delicacies.

One of the top attractions nearby is the stunning Church of San Niccolò, which is a beautiful example of Romanesque architecture. Additionally, the surrounding vineyards offer opportunities for wine tours, allowing you to sample the renowned Chianti wines. The central square is a lovely spot for a leisurely coffee or gelato, providing a superb backdrop for relaxation after a day of exploring.
How much does it cost to rent a holiday home in Radda In Chianti?
Prices for holiday rentals in Radda In Chianti 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Radda In Chianti to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Radda In Chianti holiday house rentals?
You can find great discounts on house rentals in Radda In Chianti on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Radda In Chianti?
In Radda In Chianti, villas are the most popular type of holiday rental, with around 268 available in the picturesque countryside. These villas typically offer spacious interiors, multiple bedrooms, fully equipped kitchens, and private gardens with views of the stunning Tuscan landscape. Many also feature amenities such as swimming pools, outdoor dining areas, and BBQ facilities, great for enjoying the warm Italian evenings.

Holiday houses follow closely behind, with about 64 options that provide a homely atmosphere for families or groups. These properties usually come with comfortable living spaces and outdoor areas to relax after a day of exploring the charming village and surrounding vineyards.

Additionally, there are around 52 apartments available, often situated in the heart of Radda, allowing easy access to local shops, restaurants, and cultural sites. These apartments typically include essential amenities like kitchens and living areas, suiting visitors who prefer a more urban feel while still enjoying the beauty of Tuscany.
Are there any family house rentals in Radda In Chianti?
In Radda in Chianti, Tuscany, there are numerous family-friendly homes available, with around 46 options scattered throughout the area. This picturesque town, located in the heart of the Chianti wine region, is an ideal base for families looking to explore the beautiful Tuscan countryside. Many properties offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy the fresh air and stunning views.

Visitors can expect amenities such as private pools, which provide a wonderful spot for relaxation after a day of adventure, and ample gardens superb for outdoor activities. The charming village centre is within easy reach, where families can experience local shops and delightful eateries serving traditional Tuscan cuisine.

Additionally, the surrounding area is rich in history and natural beauty, with opportunities for vineyard tours, hiking trails, and visits to nearby attractions such as castles and historical sites.
Can I rent a holiday home with a pool or hot tub in Radda In Chianti?
In Radda In Chianti, there are plenty of holiday homes available for rent that come equipped with pools and hot tubs, with approximately 82 options to choose from. This picturesque village in Tuscany offers a stunning backdrop of rolling hills and vineyards, making it an ideal destination for relaxation and indulgence.

Travellers can expect a range of amenities in these properties, including private swimming pools, some of which are set within beautifully landscaped gardens, great for soaking up the sun. Many rentals also feature hot tubs, providing a luxurious way to unwind after a day of exploring the charming local wineries and historic sites. Inside, guests will typically find well-appointed kitchens, spacious living areas, and comfortable bedrooms, ensuring a homely atmosphere during their stay.

The surrounding area is rich in culture and natural beauty, with opportunities for hiking, wine tasting, and enjoying authentic Tuscan cuisine in nearby quaint restaurants.
Can I find long-stay holiday rentals in Radda In Chianti?
A long-stay holiday rental in Radda In Chianti 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Radda In Chianti?
In Radda In Chianti, there are numerous pet-friendly house rentals available, providing a delightful experience for both travellers and their furry companions. The area is renowned for its stunning landscapes, rolling hills, and picturesque vineyards, making it an ideal setting for a relaxing getaway. Many of the holiday rentals come equipped with essential amenities such as fully equipped kitchens, outdoor spaces, and sometimes even private pools, allowing guests to enjoy the beauty of the Tuscan countryside in comfort.

The charming village itself offers a variety of local shops, restaurants, and markets, great for exploring the regional cuisine and wines. Additionally, the surrounding countryside features numerous walking trails and opportunities for outdoor activities, including hiking and wine tasting, which are enjoyable with pets.
Are there any remote work holiday rentals in Radda In Chianti?
In Radda In Chianti, Tuscany, there are numerous remote work holiday rentals available, with around 364 options for travellers to choose from. This picturesque town, known for its stunning vineyards and rich history, provides an excellent backdrop for those looking to blend work and leisure. Many properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment.

In addition to a conducive work atmosphere, guests can enjoy the charm of Tuscan living, with nearby attractions such as the medieval architecture of the town centre and the beautiful landscapes of Chianti. Many rentals also offer features like fully equipped kitchens, outdoor terraces with views of the vineyards, and access to communal gardens, enhancing the overall experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Radda In Chianti holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Radda In Chianti 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 on Vrbo 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.
When is the best time to visit Radda In Chianti for a holiday rental?
The best time to visit Radda In Chianti for a holiday rental is during the peak season from July to September, when the stunning Tuscan countryside is in full bloom. This period draws many travellers eager to indulge in the region's renowned wines and exquisite culinary experiences. The warm summer temperatures, typically ranging from 20 to 30 degrees Celsius, create a friendly space for outdoor activities such as vineyard tours and leisurely strolls through charming, sun-soaked streets.

July stands out as the most popular month, offering numerous events and festivals that showcase local culture, including wine tastings and traditional feasts. It's a vibrant time to soak in the essence of Tuscany, surrounded by fellow visitors who share your passion for exploration and enjoyment.

For those keen on a quieter experience, consider planning your visit in November. This month offers an opportunity to enjoy the tranquillity of Radda In Chianti, with fewer tourists around and a chance to witness the beautiful autumnal scenery. The cooler temperatures, averaging around 10 to 15 degrees Celsius, can be quite refreshing, making it ideal for peaceful explorations of the surrounding vineyards and olive groves.
How early should I book a Radda In Chianti holiday rental?
Book your Radda In Chianti holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Radda In Chianti?
In Radda in Chianti, visitors can immerse themselves in the picturesque landscapes and historical charm of Tuscany. The town itself is known for its stunning medieval architecture, with highlights including the impressive Church of San Niccolò and the quaint streets lined with local shops and wine cellars.

Nearby, the Chianti Classico wine region offers numerous vineyards and wineries where travellers can partake in wine tastings and tours, celebrating the area's rich viticultural heritage. The scenic countryside surrounding Radda provides ample opportunities for hiking and cycling, with trails that lead to breathtaking views of rolling hills and olive groves.

For those interested in cultural experiences, the nearby Castello di Radda is worth a visit, showcasing the region's history and offering a glimpse into the life of a Tuscan castle.
Can I change or cancel my Radda In Chianti home rental booking on Vrbo?
To find Radda In Chianti holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Radda In Chianti holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas