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Radda in Chianti vacation rentals

We found 3,042 vacation rentals — enter your dates for availability

Discover a selection of 5 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:May 22 - May 29

Image gallery for Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Aereal view, total privacy and tranquility
9.8 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Pievasciata

9% off
Price is $423
$2,964 for 7 nights
All fees included
Villa with private pool on 25 acres in the heart of Chianti, close to Siena

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Find out more about Radda in Chianti

Why visit Radda in Chianti

  • Charming Atmosphere: Radda in Chianti offers a quaint and relaxing environment surrounded by lush vineyards and rolling hills.
  • Rich History: Explore historic churches, castles, and picturesque piazzas that reflect the town's cultural heritage.
  • Exquisite Wines: Savor local wines and indulge in wine tasting experiences at nearby vineyards.
  • Outdoor Adventures: Enjoy hiking and strolling through scenic landscapes, perfect for nature lovers.
  • Welcoming Locals: Experience the friendly hospitality of the locals, enhancing your stay in this Tuscan gem.

Popular types of accommodation in Radda in Chianti

If you’re exploring vacation rentals in Radda in Chianti, you’ll find a variety of options to suit your needs. The most popular accommodations include charming apartments, luxurious villas, and houses, all featuring inviting dining areas. While you’re here, don’t miss nearby attractions like Castello Monterinaldi, Palazzo Leopoldo Hotel, and Castello di Ama, which enhance your stay with local culture and stunning scenery.

  • Apartments: A top favorite among travelers, apartments in Radda in Chianti offer a stylish and convenient base for exploring the region.
  • Villas: Indulge in luxury with villas, providing spacious accommodations and stunning views of the Tuscan landscape.
  • Houses: Perfect for families or groups, these homes offer a cozy atmosphere and homey amenities.
  • Caravan Parks: For a unique experience, caravan parks provide a blend of outdoor adventure and comfort.
  • Cottages: These charming retreats offer a quaint and intimate setting, ideal for a peaceful getaway.**

Top attractions in and around Radda in Chianti

Radda in Chianti is perfect for romantic getaways and outdoor adventures, offering a blend of culture and entertainment. Visitors can explore charming churches, historic castles, and picturesque piazzas, making it an ideal destination for those seeking a rich city experience infused with romance. Whether you're wandering through the local streets or enjoying the stunning landscapes, Radda in Chianti promises unforgettable moments.

  • Castello di Albola: Nestled in Radda in Chianti, this romantic castle offers a captivating glimpse into the region's rich history and culture, complete with stunning views of the surrounding vineyards.
  • Piazza del Campo: Located 12 miles from Radda, this vibrant square is renowned for its unique shell shape and serves as a cultural hub, bustling with lively events and local gatherings.
  • Siena Cathedral: Just 12 miles away, this magnificent cathedral showcases stunning Gothic architecture and intricate artworks, providing a deep dive into the region’s artistic heritage.

Things to do recommended for couples

If you’re seeking a romantic getaway in Radda in Chianti, explore the charming Il Molino di Grace Winery and Badia a Coltibuono, both offering enchanting atmospheres. For a touch of luxury, visit the Villa a Sesta Polo Club, perfect for couples looking to unwind and indulge.

Things to do recommended for families

Families visiting Radda in Chianti can experience the excitement of the Siena Stadium and Stadio Artemio Franchi, both offering thrilling sports vibes, just 11 and 12 miles away. For an adventurous twist, try the nearby Siena Circuit for an exhilarating karting experience, located 13 miles away.

Things to do recommended for groups

Shop at The Mall Luxury Outlet for a blend of luxury and entertainment, hike the scenic Sentierelsa Trail for outdoor adventure, or savor local wines at Enoteca Italiana to experience the rich flavors of Tuscany. These activities promise a memorable group vacation in Radda in Chianti.

*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 planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your preferences in the search filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Radda in Chianti with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas 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 tough. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private 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 vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with food bowls and cozy beds, ensuring that all family members, including your pet, feel comfortable and at home.
  • Planning for a long term stay visiting Radda in Chianti: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Radda in Chianti

Radda in Chianti is a charming Tuscan gem perfect for a romantic and outdoor getaway. Nestled among lush vineyards and rolling hills, this quaint town offers a relaxing atmosphere with friendly locals and rich history. Explore nearby Chianti towns, savor exquisite wines, and immerse yourself in breathtaking scenery. With its picturesque streets and vibrant culture, Radda in Chianti is an ideal destination for travelers seeking both adventure and tranquility.

  • Chianti Region: The Chianti Region, located approximately 3 miles from Radda in Chianti, is renowned for its romantic landscapes and outdoor activities. This picturesque area invites travelers to indulge in spa treatments and explore charming local stores. You'll find a treasure trove of historic sites and landmarks, perfect for those who appreciate culture and history. From wine tasting to leisurely walks through vineyards, the Chianti Region offers a delightful blend of entertainment and relaxation, making it a must-visit for anyone seeking a taste of Tuscany.
  • Villa: Nestled within the enchanting area of Radda in Chianti, the village of Villa is a haven for those looking for a romantic getaway or an outdoor adventure. Visitors can immerse themselves in the local culture by exploring the vibrant public market, where fresh produce and artisanal goods abound. Guided tours provide insight into the fascinating history of the area, while nearby attractions such as captivating castles and serene lakes enhance the experience. The ambiance of Villa, with its charming streets and welcoming atmosphere, promises an unforgettable visit.
  • Volpaia: Volpaia is a quaint village located near Radda in Chianti that offers visitors a perfect blend of romance and outdoor experiences. Known for its tranquil environment, travelers can enjoy rejuvenating spa services while soaking in the stunning scenery. The village is home to significant historical monuments and a captivating castle, making it an ideal destination for history enthusiasts. Whether you’re wandering through the charming streets or savoring local wines, Volpaia provides an enchanting escape into the heart of Tuscany.

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

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a significant difference, as prices can vary. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.

Unlock savings with One Key

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

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform to plan new trips, manage your ongoing arrangements, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover Trip Boards, please 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:

  • Chianti Sculpture Park (6.5 mi / 10.4 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)
  • Sentierelsa Trail (12.8 mi / 20.6 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, 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.

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