Radda in Chianti vacation rentals

We found 3,005 vacation rentals — enter your dates for availability

Discover a selection of 17 homes, 15 apartments, and other vacation rentals in Radda in Chianti that are perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, like WiFi and a washer and dryer. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Radda in Chianti

Showing deals for:Feb 27 - Mar 6

Image gallery for Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Private pool
9.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

San Casciano in Val di Pesa, Tuscany

20% off
Price is CA $844
CA $6,516 total
includes taxes & fees
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

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Find out more about Radda in Chianti

Why people love visiting cozy Radda in Chianti

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

Activities and attractions in Radda in Chianti

Are you looking for attractions to visit in the area? Venture out of your vacation home and experience everything that makes Radda in Chianti a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Cantalici Winery (5.3 mi / 8.5 km)

Exploring the natural landscape of Radda in Chianti

Whether you're an active traveler 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 eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Sentierelsa Trail (12.8 mi / 20.6 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)
  • Chianti Sculpture Park (6.5 mi / 10.4 km)
  • Le Caldane Thermal Baths (13.6 mi / 21.9 km)

How to get to and around Radda in Chianti

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

Frequently asked questions

What is the best area to stay in Radda In Chianti when booking a vacation rental?
When considering a vacation rental in Radda in Chianti, Tuscany, the historic centre is an ideal area to stay. This charming neighbourhood is characterised by its medieval architecture, cobblestone streets, and picturesque views of the surrounding vineyards and hills. Here, you'll find a variety of properties, ranging from cosy apartments to more spacious villas, making it a popular choice for visitors seeking a truly authentic Tuscan experience.

One of the top attractions in the historic centre is the Church of San Niccolò, which dates back to the 14th century and features stunning frescoes. Just a short stroll away, you can visit the Palazzo del Podestà, a beautiful medieval building that showcases the town's rich history. The central piazza is also a lovely spot to relax, with charming cafés and shops nearby, providing a superb place to enjoy a morning coffee or a glass of local Chianti wine.
How much does it cost to rent a vacation home in Radda In Chianti?
Prices for vacation 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 travelling 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.
Are there any discounts for Radda In Chianti vacation 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 vacation rental accomodation in Radda In Chianti?
In Radda In Chianti, villas are the most popular type of vacation rental, with about 79 available in the area. These splendid properties often boast spacious interiors, multiple bedrooms, fully equipped kitchens, and beautiful outdoor spaces featuring private gardens and swimming pools, superb for enjoying the stunning Tuscan landscape. Additionally, there are around 16 apartments, which provide a more compact yet comfortable option, typically including living areas and kitchen facilities, ideal for couples or smaller groups. Vacation houses and several cottages are also available, offering a rustic charm and a homey atmosphere, suiting those seeking a peaceful retreat in the heart of Tuscany.
Are there any family house rentals in Radda In Chianti?
In Radda In Chianti, Tuscany, there are numerous family-friendly vacation rentals available, with around 48 options to choose from. This charming town, located in the heart of the Chianti wine region, offers a superb backdrop for family getaways. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor terraces or gardens for children to enjoy.

Visitors can explore the beautiful countryside, with vineyards and olive groves offering stunning views and opportunities for wine tastings. The area is also rich in history, with nearby attractions such as the medieval castles and the picturesque town centre, where local shops and eateries provide a taste of authentic Tuscan life.
Can I rent a vacation home with a pool or hot tub in Radda In Chianti?
In Radda In Chianti, there are plenty of vacation homes available for rent that feature pools or hot tubs, with around 91 options to choose from. This picturesque town in Tuscany is renowned for its stunning vineyards and rolling hills, making it a superb getaway for those seeking relaxation and natural beauty. Many of these properties come with amenities such as private swimming pools, outdoor terraces with breathtaking views, and hot tubs for unwinding after a day of exploring the Chianti region.
Can I find long-stay vacation rentals in Radda In Chianti?
A long-stay vacation 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, travellers can find a variety of pet-friendly house rentals that offer a charming Tuscan experience. With around 59 options available, many of these properties are located among the picturesque vineyards and rolling hills of the Chianti region. Expect amenities such as spacious outdoor terraces, private gardens, and fully equipped kitchens, great for enjoying the local cuisine. Some rentals even feature swimming pools, making them ideal for a relaxing vacation.
Are there any remote work vacation rentals in Radda In Chianti?
In Radda In Chianti, Tuscany, there are numerous remote work vacation rentals available, with around 106 options to choose from. This picturesque village, located in the heart of the Chianti wine region, provides an inspiring backdrop for those looking to blend work and leisure. Many properties cater specifically to remote workers, featuring dedicated workspaces equipped with desks and chairs, high-speed Wi-Fi, and safety deposit boxes for peace of mind. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Radda In Chianti vacation rentals with parking?
Vrbo offers a wide selection of vacation 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.
What are popular rental amenities in Radda In Chianti?
In Radda In Chianti, popular rental amenities typically include private pools, kitchens, and refrigerators, making them ideal for those looking to self-cater during their stay. Many properties also feature dishwashers for added convenience. These amenities are particularly desirable as visitors often enjoy preparing meals with local ingredients while soaking in the stunning Tuscan countryside views.
When is the best time to visit Radda In Chianti for a vacation rental?
The most popular time to visit Radda In Chianti is during the summer months, particularly in July. This period marks the peak season, attracting travellers eager to immerse themselves in the stunning Tuscan landscape and enjoy the region's renowned wine culture. With warm temperatures averaging around 30°C, visitors can partake in outdoor activities such as vineyard tours, wine tastings, and exploring the charming medieval streets of Radda.

From July through September, the atmosphere is vibrant and lively, great for those looking to engage with local festivals and events celebrating the rich heritage of the area. The warm evenings are ideal for al fresco dining, allowing you to savour exquisite regional cuisine while surrounded by breathtaking views of the rolling hills.

If you're seeking a more tranquil experience, consider visiting in November. This month not only offers a quieter ambiance but also a unique opportunity to explore the beauty of the vineyards as they prepare for the winter months. The fall colours can still be stunning, and you'll enjoy a more intimate experience with the local culture, often with fewer crowds.
How early should I book a Radda In Chianti vacation rental?
Book your Radda In Chianti vacation 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 vacation 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 take part in the charm of this picturesque Tuscan village. The historic centre, with its narrow streets and medieval buildings, is home to the beautiful Church of San Niccolò, which dates back to the 14th century. Nearby, the Piazza Ferrucci offers a lovely spot for enjoying local wines and delicacies at quaint cafes and eateries.

For wine enthusiasts, exploring the surrounding Chianti Classico region is a must. Many vacation rentals in Radda provide easy access to renowned vineyards and wineries, where guests can indulge in tastings and tours. The scenic countryside, dotted with olive groves and vineyards, invites leisurely walks and cycling adventures, showcasing the stunning landscapes of Tuscany.
Can I change or cancel my Radda In Chianti home rental booking on Vrbo?
To find Radda In Chianti vacation 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 vacation 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.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.

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