Photo by Davide Taviani

Radda in Chianti vacation rentals

We found 3,033 vacation rentals — enter your dates for availability

Discover a selection of 6 homes 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:Jun 12 - Jun 19

Image gallery for PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Pool
10 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)

PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Castelnuovo Berardenga

9% off
Price is $899
$6,296 for 7 nights
All fees included
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Radda in Chianti

Why visit Radda in Chianti

  • Romantic Landscapes: Experience stunning views of the Chianti hills and picturesque vineyards, perfect for couples seeking a romantic getaway.
  • Cultural Richness: Explore enchanting churches, historic castles, and palatial sites that showcase the region's rich history.
  • Charming Streets: Wander through quaint streets filled with vibrant local culture and delightful shops.
  • Exquisite Wines: Indulge in world-class wines and local culinary delights that Radda is renowned for.
  • Luxurious Accommodations: Choose from stunning villas and cozy apartments for a perfect home base during your stay.

Popular types of accommodation in Radda in Chianti

If you're looking for the perfect getaway in Radda in Chianti, you're in the right place. Our vacation rentals include a variety of accommodations, with the most popular options being stunning villas, cozy apartments, and houses. Whether you're searching for a luxurious villa in Chianti or a charming apartment, we have a range of villa rentals to suit every traveler’s needs. Experience the beauty of Radda in Chianti with the perfect home base.

  • Apartments: The top choice for travelers in Radda in Chianti, offering convenient amenities and a home-like atmosphere.
  • Villas: A popular option providing spacious living and luxurious surroundings, perfect for families or groups.
  • Houses: Ideal for those wanting a personal touch, these homes offer comfort and privacy.
  • Caravan Parks: A unique choice for adventure seekers, combining outdoor experiences with cozy accommodations.
  • Cottages: Quaint and charming, these provide a cozy retreat amidst the beautiful Tuscan landscape.**

Top attractions in and around Radda in Chianti

Radda in Chianti is a charming destination perfect for a romantic outdoor getaway. Explore the enchanting churches, historic castles, and palatial sites that offer rich cultural experiences. Don't miss the stunning views of the Chianti hills and the picturesque vineyards. Whether you're wandering through the quaint streets or visiting the elegant Italian villas, Radda promises unforgettable moments for couples and travelers alike. Plan your trip to discover the beauty of this Tuscan gem.

  • Castello di Albola: Nestled in Radda in Chianti, this enchanting castle offers a romantic atmosphere and a glimpse into the region's rich culture. Explore its beautiful surroundings and indulge in local wine tastings.
  • Piazza del Campo: Located 12 miles away, this iconic square is renowned for its stunning medieval architecture and vibrant city vibes. It hosts the famous Palio horse race, bringing a unique cultural experience.
  • Fortezza Medicea: Also situated 12 miles from Radda, this historic fort features impressive architecture and a deep sense of history. Explore its grounds and enjoy panoramic views of the surrounding area.

Things to do recommended for couples

Ready for a romantic getaway in Radda in Chianti? Visit the luxurious Villa a Sesta Polo Club, located 12 miles away. Enjoy the stunning countryside while indulging in exceptional activities, perfect for couples looking to create unforgettable memories together.

Things to do recommended for families

Families will love exploring the charming streets of Radda in Chianti, visiting local vineyards for juice tastings, and enjoying scenic bike rides through the beautiful countryside. Don't miss the fun at nearby adventure parks, offering zip-lining and hiking trails suitable for all ages.

Things to do recommended for groups

Experience a guided wine tour at local vineyards, savoring Chianti's finest wines. Enjoy a hands-on cooking class to create authentic Tuscan dishes and explore the charming streets of Radda while discovering its rich history and stunning landscapes, perfect for group bonding and adventure.

*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 traveling with a group, family, pets, or planning an extended stay, it’s important to prioritize your filters accordingly. Here are some helpful tips for booking on Vrbo.

  • Traveling to Radda in Chianti with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Radda in Chianti with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Radda in Chianti: For many families, a getaway isn't truly special without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with 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 vacation rentals that offer great deals for stays of a month or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Radda in Chianti

Discover the enchanting charm of Radda in Chianti, where romantic landscapes and vibrant local culture await. This picturesque town in Tuscany invites you to explore its historical streets, indulge in exquisite wines, and enjoy the serene beauty of the surrounding countryside. Just a short drive away, you’ll find charming villages and luxurious accommodations, perfect for a secluded getaway. Experience the warm hospitality of friendly locals as you immerse yourself in the delightful atmosphere of this stunning region.

  • Chianti Region: Located a mere 3 miles from Radda in Chianti, the Chianti Region is a picturesque landscape characterized by rolling hills, vineyards, and olive groves. Travelers flock here for a romantic escape, outdoor adventures, and vibrant entertainment options. Enjoy rejuvenating spa treatments or explore the charming historic sites, including ancient castles and monuments that tell the story of this enchanting area. Whether you're wandering through the countryside or indulging in local cuisine, the Chianti Region offers a quintessential Tuscan experience.
  • Villa: Nestled within the Radda in Chianti area, Villa is a quaint village that invites visitors to immerse themselves in its romantic atmosphere and outdoor beauty. Known for its engaging tours, Villa showcases the rich history and cultural heritage of Tuscany. While exploring this charming village, be sure to visit its historic landmarks, including impressive castles and a serene botanical garden. Whether you're hiking through scenic trails or enjoying local delicacies, Villa promises a delightful getaway.
  • Volpaia: Volpaia is a charming village located close to Radda in Chianti, attracting travelers seeking a blend of romance, outdoor activities, and entertainment. Here, you can experience unique transportation options like cable cars and funiculars while enjoying stunning views of the surrounding countryside. Volpaia is also home to historic places, monuments, and castles that reflect its rich past. With a variety of spas and wellness experiences available, you can unwind after a day of exploration in this enchanting village.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 simple

Looking to cut costs on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. When you enroll in our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for planning your adventures. You can start new trips, resume your previous ones, or manage your itinerary all in one place. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring the features of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Chianti Sculpture Park (6.5 mi / 10.4 km)
  • Gianfranco Carla Fineschi Botanical Rose Garden (7.3 mi / 11.8 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, Tuscany, Italy when booking a vacation rental?
When considering the best area to stay in Radda In Chianti, Tuscany, you'll find that the historic center offers a charming experience with its picturesque streets and local ambiance. This area is packed with delightful eateries and quaint shops, allowing visitors to immerse themselves in the authentic Tuscan lifestyle. A must-visit attraction is the stunning Church of San Niccolò, which showcases beautiful architecture and provides a glimpse into the region's rich history.

Another fantastic option is the surrounding countryside, where you can find numerous vacation rentals located among the rolling hills and vineyards that define the Chianti landscape. This area is great for those looking to enjoy breathtaking views and partake in wine tasting experiences at local wineries, making it an ideal retreat for wine enthusiasts. With a variety of properties available, from rustic villas to modern apartments, you'll have plenty of choices to suit your preferences.
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 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 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 common type of vacation rental, with about 67 available throughout the picturesque Tuscan countryside. These villas often feature stunning views, spacious layouts, private pools, and outdoor dining areas, making them ideal for travelers looking to enjoy the serene landscape and local vineyards. Additionally, there are around 16 vacation houses that provide a similar charm, offering cozy interiors and garden spaces for relaxation. For those seeking a more compact option, approximately 13 apartments are available, typically equipped with kitchens and comfortable living spaces. A few cottages are also scattered around, providing a quaint and rustic atmosphere for a tranquil getaway.
Are there any family house rentals in Radda In Chianti?
In Radda In Chianti, Tuscany, there are numerous family-friendly houses available, with around 46 options for travelers to choose from. This charming town, located in the heart of the Chianti wine region, offers a picturesque setting for families seeking a memorable getaway. Many of these homes boast spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces where children can play and adults can unwind while soaking in the stunning landscapes.

Visitors can explore nearby attractions like the historic Castello di Radda and enjoy scenic walks through vineyards and olive groves. Additionally, the region is known for its culinary delights, with many local trattorias serving authentic Tuscan dishes just a short drive away.
Can I rent a vacation home with a pool or hot tub in Radda In Chianti?
In Radda In Chianti, there are numerous vacation homes available for rent with pools or hot tubs, with around 82 options to choose from. This picturesque town, located in the heart of Tuscany, offers a variety of charming properties that often feature stunning views of the surrounding vineyards and rolling hills. Many of these rentals come with private pools, inviting hot tubs, and spacious outdoor terraces, superb for enjoying the beautiful weather and scenic landscapes.

Travelers can expect amenities like fully equipped kitchens for preparing local Tuscan cuisine, air conditioning for comfort during warm months, and cozy living spaces that enhance relaxation after a day of exploring the region. The town itself is rich in history and culture, with local wineries and quaint shops nearby, making it an ideal destination for those looking to unwind while experiencing the beauty of Tuscany.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Radda In Chianti?
In Radda In Chianti, there are numerous pet-friendly house rentals available, offering a range of amenities and picturesque surroundings. Travelers can expect accommodations that often include features such as fully equipped kitchens, spacious living areas, and outdoor spaces like terraces or gardens, superb for relaxing while enjoying the stunning views of the Tuscan countryside.

The area is rich in vineyards and olive groves, providing an excellent backdrop for leisurely walks or hikes with pets. Nearby attractions such as the Chianti Classico wine region and charming medieval villages enhance the experience, allowing visitors to explore local culture and cuisine. Radda itself is a quaint town with pet-friendly cafes and restaurants, making it easy to include furry companions in your travel plans.
Are there any remote work vacation rentals in Radda In Chianti?
In Radda In Chianti, there are numerous remote work vacation rentals available, with around 91 options to choose from. This picturesque town in Tuscany is not only known for its stunning vineyards and rolling hills but also offers a variety of properties that cater to remote workers. Many rentals come equipped with high-speed Wi-Fi, dedicated workspaces, and comfortable seating to ensure an efficient working environment.

Travelers can expect to find charming accommodations ranging from rustic villas to modern apartments, often featuring amenities such as fully equipped kitchens, outdoor terraces, and beautiful views of the surrounding countryside. The local area provides a serene atmosphere ideal for balancing work and leisure, with opportunities to explore the historic town center, visit local wineries, and enjoy the rich culinary scene. 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 travelers 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 vacation rental amenities cater to travelers seeking a comfortable and relaxing stay in this picturesque Tuscan village. Many rentals feature well-equipped kitchens, allowing guests to prepare their own meals using local ingredients. A coffee and tea maker is commonly available for those who enjoy a warm beverage in the morning.

Private pools are also a sought-after amenity, providing a tranquil space to unwind while enjoying the stunning views of the surrounding vineyards and hills. Additionally, many properties come with fireplaces, creating a cozy atmosphere, especially during the cooler months. Onsite parking is another convenient feature, making it easy for visitors to explore the charming streets of Radda and the beautiful Chianti region.
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, Tuscany, Italy?
In Radda In Chianti, visitors can take part in the rich wine culture and stunning landscapes of Tuscany. The town itself is charming, with its medieval architecture and picturesque streets, offering attractions such as the historic Church of San Niccolò and the scenic views from the town's viewpoints.

Nearby, the Chianti Classico Wine Museum provides insight into the region's renowned wine production, and numerous vineyards offer tours and tastings, allowing travelers to experience the local varietals firsthand. The surrounding countryside is superb for outdoor enthusiasts, with opportunities for hiking and cycling along scenic trails that weave through the vineyards and olive groves.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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 Vacation Ideas