Radda in Chianti vacation rentals

We found 2,986 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.
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Find out more about Radda in Chianti

Find out more about Radda in Chianti

Why visit Radda in Chianti

  1. Romantic atmosphere: Radda in Chianti is an idyllic destination for couples, offering a charming ambiance perfect for lovebirds.
  2. Rich cultural heritage: Explore stunning churches, picturesque piazzas, and engaging museums that showcase the area's history.
  3. Scenic countryside: Discover breathtaking landscapes dotted with stunning villas and vineyards in the beautiful Chianti region.
  4. Outdoor adventures: Enjoy hiking and exploring the picturesque nature surrounding Radda for an active getaway.
  5. Diverse accommodations: Choose from charming apartments, luxurious villas, and cozy retreats to enhance your stay.

Popular types of accommodation in Radda in Chianti

If you're planning a getaway to Radda in Chianti, the excitement begins with selecting the perfect accommodation. This charming Tuscan village offers a variety of vacation rentals, including cozy apartments, scenic caravan parks, and stunning houses. Whether you're dreaming of a luxurious Tuscany villa or a quaint villa Rignana, you'll find the ideal spot to unwind and soak in the beauty of the Chianti region.

  • Apartments: The top choice for travelers in Radda in Chianti, offering convenient amenities and a home-like atmosphere.
  • Caravan Parks: A popular option for those seeking a unique outdoor experience with facilities for camping and mobile homes.
  • Houses: Ideal for families or groups, these homes provide privacy and comfort during your stay.
  • Villas: Luxurious and spacious, villas offer a taste of the Tuscan lifestyle with stunning views.
  • Lodges: A cozy retreat option that combines rustic charm with modern comforts in a picturesque setting.**

Top attractions in Radda in Chianti

Radda in Chianti is a charming destination perfect for romance and outdoor adventures. Visitors can explore stunning churches, picturesque piazzas, and engaging museums that reflect the area's rich culture. Ideal for those seeking a romantic experience, Radda offers private tours and opportunities to delve into the beautiful Chianti region. Whether you're enjoying the local architecture or savoring the Tuscan landscape, this quaint village has something for everyone.

  1. Castello di Albola: Nestled in the heart of Radda in Chianti, this enchanting castle offers a romantic atmosphere and rich cultural heritage. Explore its stunning architecture and picturesque vineyards, perfect for wine tasting and soaking in the Tuscan countryside.
  2. Piazza del Campo: Located 12 miles from Radda, this vibrant square is famous for its unique shell shape and historic ambiance. It's a cultural hub where locals and tourists gather, providing a great spot to enjoy local cuisine and people-watch.
  3. Siena Cathedral: Also 12 miles away, this magnificent cathedral features stunning Gothic architecture and intricate artworks. A must-visit for its breathtaking interiors and spiritual significance, it embodies the rich cultural tapestry of Siena.

Things to do recommended for couples

Experience romance in Radda in Chianti! Visit Il Molino di Grace Winery for a cozy wine tasting, indulge in luxury at Villa a Sesta Polo Club, or unwind at San Giovanni Terme Rapolano for a blissful spa day. Each offers a unique touch to your couple's getaway.

Things to do recommended for families

In Radda in Chianti, families can explore the Chianti Observatory for a fun planetarium experience, race at the Siena Circuit for an adrenaline-filled karting adventure, or cheer on teams at the nearby Siena Stadium, making for an unforgettable family vacation in Tuscany.

Things to do recommended for groups

Explore the luxury shops at The Mall Luxury Outlet, savor exquisite wines at Enoteca Italiana, or embark on an adventure along the scenic Sentierelsa Trail. Each experience offers a unique taste of Radda in Chianti, perfect for group travelers seeking unforgettable moments.

What do I need to keep in mind when booking a vacation in Radda in Chianti

If you're traveling with a group, family, or pets, or if you're seeking longer stays, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Radda in Chianti with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Radda in Chianti with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with having 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 vacation isn’t truly complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Radda in Chianti: If you're in search of vacation rentals with discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider additional amenities like a parking space, a well-equipped kitchen, or a private pool when refining your search.

Where to stay in Radda in Chianti

Radda in Chianti is a gem in Tuscany, perfect for romantic getaways and outdoor adventures. Explore the charming towns of Gaiole in Chianti and immerse yourself in the beautiful countryside, where stunning villas dot the landscape. Experience the friendly atmosphere of the Chianti region, rich in history and secluded charm, offering a serene escape for travelers seeking unforgettable moments in the heart of Tuscany.

  • Florence: Located approximately 20 miles from Radda in Chianti, Florence is a cultural treasure trove that draws visitors from around the globe. This historic city is renowned for its art, architecture, and rich history, making it a perfect day trip for travelers seeking to immerse themselves in the Italian Renaissance. Stroll through the bustling shopping areas, visit the famous public markets, and explore iconic landmarks like the Duomo and Ponte Vecchio. Florence offers a vibrant atmosphere filled with museums, historic sites, and a variety of dining options, ensuring a memorable experience for families and outdoor enthusiasts alike.
  • Villa: Nestled in the heart of Chianti, Villa offers a charming escape known for its romantic ambiance and outdoor activities. This picturesque town is perfect for couples looking for a getaway, featuring lovely markets and public market venues where you can sample local delicacies. Enjoy scenic tours that showcase the stunning Tuscan landscape, dotted with castles and serene lakes. Villa is an ideal spot for those seeking entertainment and relaxation, making it a delightful addition to your Radda itinerary.
  • Volpaia: Located near Radda in Chianti, Volpaia is a quaint village that enchants visitors with its historic charm. Known for its romantic atmosphere and outdoor experiences, it invites travelers to explore its beautiful landscape and historic sites. Discover monuments and historic palaces that reflect the village's rich heritage. The picturesque streets and stunning views of the surrounding vineyards create a perfect setting for leisurely strolls, making Volpaia a must-visit for those seeking a blend of culture and tranquility.

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)SunnyAverageAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
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 aiming to cut costs on your upcoming journey? One helpful tip is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow down your options by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner definitely has its perks! By enrolling in our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can start new trips, continue from where you paused, or manage your existing plans all in one place. Your saved or booked properties will be neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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:

  • 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 (6.4 mi / 10.3 km)
  • Area Naturale Protetta di Interesse Locale Arboreto Monumentale di Moncioni (6.9 mi / 11.1 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 when booking a vacation rental?
If you’re thinking of a getaway to Radda in Chianti, Colle Petroso is one of the most popular places to stay. Whether you select a condo, cottage or another property type, you’ll always have the whole place to yourself.
What is the most popular type of vacation rental accommodation in Radda in Chianti?
According to our data, villas are considered the most popular property type in Radda in Chianti. But as you’d expect, everyone’s idea of an epic stay will differ. Vrbo has vacation homes of all shapes, sizes and budgets, so you’re sure to find the perfect fit for you.
How much does it cost to rent a vacation rental in Radda in Chianti?
Several things can affect the price of a vacation rental in Radda in Chianti, like the length of stay, type of property and season. Still, all Vrbo homes have something in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Radda in Chianti?
Prices for beach houses in Radda in Chianti vary depending on the type and size of the property and when you’re traveling. All you need to do is enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use our filter tool to narrow down your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Radda in Chianti?
Yes. There are. You can pick from 101 vacation rentals that allow pets in Radda in Chianti. Many of our pet-friendly vacation rentals come with an outdoor space for your furry friend to run around in, special dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Radda in Chianti?
Grab your swimming gear and inflatable unicorn, because there are 86 houses with a private pool in Radda in Chianti. Book a stay at one of these terrific vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then use the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Radda in Chianti?
When it comes to rental amenities that people prefer in Radda in Chianti, a swimming pool, a barbecue grill and a sauna rank highest. With Vrbo vacation homes, you’ll find options to fit your taste and style, whether you’re going on a vacation with friends, relatives or even pets.
Are there large group vacation rentals in Radda in Chianti?
You can choose from 42 vacation rentals in Radda in Chianti that can accommodate a group of 10 or more guests. Whether you’re planning time away with extended family or an event like an anniversary, there’s enough space to get your loved ones together under the same roof.
Are there vacation rentals in Radda in Chianti that welcome kids?
Radda in Chianti has 101 family-friendly vacation rentals to pick from. And finding a stay that welcomes youngsters is simple with Vrbo’s “Properties good for families” filter. On top of having the whole place to yourselves, you’ll get access to amenities and perks like extra bedrooms, full kitchens and yards.
What are the top attractions for families in Radda in Chianti?
If you’ve got the kids in tow, make sure you put these family-friendly attractions in Radda in Chianti on your list of things to do:

  • Castello di Albola
  • Castello di Radda Winery

Are there one-bedroom vacation rentals in Radda in Chianti?
Take your pick from 10 one-bedroom rentals in Radda in Chianti. Whether you’re on the lookout for a comfy cottage or an upmarket condo, our one-bedroom properties are ideal if you don’t require tons of space. One of the best parts about having your own pad? You won’t have to share your vacation with strangers.
Can I find two-bedroom vacation rentals in Radda in Chianti?
Choose from 19 two-bedroom rentals in Radda in Chianti. Give your little ones the second room or fill it with a couple of your best buddies. There’s ample space for whoever’s lucky enough to be coming along for the ride.
Are there vacation rentals with WiFi in Radda in Chianti?
Whether you’d like to keep up with the news, reply to emails or update your social media accounts, there are 44 vacation homes with WiFi in Radda in Chianti. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Radda in Chianti?
There are 36 vacation rentals with air conditioning in Radda in Chianti providing that cooling breeze and extra element of comfort. Simply enter your preferred travel dates and then take advantage of our filters to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in Radda in Chianti?
The age limit can differ between properties on Vrbo, so look at the rules of the vacation rental in Radda in Chianti you want. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Radda in Chianti for?
How long you can book a vacation rental in Radda in Chianti differs according to the property. Simply enter your preferred travel dates to display a list of options offering extended stays. With many creature comforts like air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you’re sure to get a terrific place to call your home away from home in Radda in Chianti.
Does Vrbo offer discounts for vacation homes in Radda in Chianti?
In Radda in Chianti, you’ll find great discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a weekend escape or a few weeks away, we have a variety of options that’ll suit your style.

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