Holiday Rentals in Radda in Chianti

1077 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Radda in Chianti holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Radda in Chianti

Best Holiday Rentals for Families in Radda in Chianti

Travelling to Radda in Chianti with children? A quality family holiday rental or Airbnb makes everything easier with city attractions nearby.

Borgo Livernano - Radda in Chianti
9.2 566 reviews
Radda in Chianti
05/09 – 19/09
£299/nighttotal: £4186 (14 )

Borgo Livernano

1 2
farm , Radda in Chianti
Borgo Livernano is a farmhouse located in the Chianti Hills, just 30km from Siena and 60km from Florence, surrounded by forests, vineyards, and olive groves, offering a peaceful escape in the Tuscan countryside. It has received very good ratings for its location, cleanliness, and overall experience.
The farmhouse has been carefully restored, preserving its original charm and character, and offers two guest houses furnished with local antiques. Guests can enjoy a swimming pool, a jacuzzi, a terrace, a garden, a spa, a restaurant, a bar, and parking, as well as the farm's own wine, olive oil, honey, vegetables, and fruits.
Relax & Piscina: Oasi Nel Cuore Del Chianti - Radda in Chianti
9.7 341 reviews
Radda in Chianti
27/06 – 04/07
£125/nighttotal: £875 (7 )

Relax & Piscina: Oasi Nel Cuore Del Chianti

2 2
apartment , Castellina in Chianti
This charming apartment is located in the Borgo di Tregole, a small village just 5km from Castellina in Chianti, offering a peaceful escape amidst the picturesque Chianti Classico hills. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The two-bedroom apartment comfortably sleeps four guests and is equipped with everything needed for a relaxing stay. Guests can enjoy a private garden, a shared pool, and a jacuzzi, making it perfect for families and groups looking for a memorable Tuscan getaway.
La Casina - Radda in Chianti
9.9 109 reviews
Radda in Chianti
27/06 – 04/07
£94/nighttotal: £658 (7 )

La Casina

1 2
apartment , Radda in Chianti
This recently renovated 70 sq m apartment is situated near Radda in Chianti's historic centre, only 0.1 km from a supermarket and bank.
The self-catering property offers one bedroom, one bathroom, sleeps four, and features a private entrance, spacious living room with a double sofa bed, a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking, and a loggia with views of the Chianti countryside.
Tenuta Il Poggetto - Radda in Chianti
9.2 20 reviews
Radda in Chianti
27/06 – 04/07
£173/nighttotal: £1211 (7 )

Tenuta Il Poggetto

1 2
house , Radda in Chianti
Tenuta il Poggetto, a self-catering house in Radda in Chianti, enjoys a peaceful countryside setting, conveniently located 21km from Piazza Matteotti and 32km from Piazza del Campo, offering easy access to major Tuscan landmarks.
This pet-friendly property features a fully equipped kitchen, private patio with barbecue, garden, free Wi-Fi, and parking, perfect for families seeking a relaxing Tuscan getaway with walking opportunities nearby.

Top Holiday Rentals with Parking in Radda in Chianti

A car park at your holiday rental in Radda in Chianti means exploring the city centre is easy every day with no extra faff. Find your perfect stay.

Holiday Home Le Bonatte By Interhome - Radda in Chianti
10 43 reviews
Radda in Chianti
27/06 – 04/07
£134/nighttotal: £938 (7 )

Holiday Home Le Bonatte By Interhome

2 2
house , Radda in Chianti
Holiday Home Le Bonatte is situated in Radda in Chianti, Tuscany, conveniently located 34km from Siena and 56km from Florence.
This five-bedroom, five-bathroom villa sleeps large groups, boasting a terrace, garden, swimming pool, Wi-Fi, parking, and a fully equipped kitchen including a fridge, freezer, and microwave; ideal for families seeking self-catering holidays in the Chianti region.
Charming Tuscan Suite With Pool 2 To 5 Persons Lamole Greve In Chianti - Radda in Chianti
9.5 15 reviews
Radda in Chianti
11/09 – 14/09
£182/nighttotal: £546 (3 )

Charming Tuscan Suite With Pool 2 To 5 Persons Lamole Greve In Chianti

2 3
apartment , Greve in Chianti
This Tuscan apartment, situated in Lamole, a district of Greve in Chianti, is 13.4 km from Piazza Matteotti and approximately 40 km from Florence's attractions including the Uffizi Gallery and Piazza Michelangelo.
The 80-square-metre self-catering suite sleeps nine, boasting two bedrooms, a bathroom, a private terrace with barbecue, a private pool, and access to nearby hiking and cycling trails.
Il Ghiro N°8 By Interhome - Radda in Chianti
9.0 2 reviews
Radda in Chianti
05/09 – 19/09
£98/nighttotal: £1372 (14 )

Il Ghiro N°8 By Interhome

2 2
apartment , Gaiole in Chianti
This detached villa, 'Il Ghiro n°8', is located 10 kilometres from Gaiole in Chianti's centre, offering panoramic views of the Chianti hills and is 18 kilometres from Castello di Brolio.
This 65 square metre apartment accommodates up to four guests across two bedrooms and features a living room with a double sofa bed, a kitchen with a fridge, free WiFi, and shared access to a 2-hectare garden with a swimming pool and volleyball court.
Aia 5 People In To The Heart Of Gallonero - Radda in Chianti
9.0 86 reviews
Radda in Chianti
05/09 – 19/09
£95/nighttotal: £1330 (14 )

Aia 5 People In To The Heart Of Gallonero

1 2
apartment , Greve in Chianti
"La Vigna" is a charming converted barn located just 15km from Figline Valdarno, with a train station offering frequent connections to Florence. This property has received consistently excellent ratings for its location, cleanliness, and overall experience.
The apartment features two bedrooms and two bathrooms, providing ample space for families or groups. Guests can enjoy a private garden with a barbecue, a shared swimming pool, and access to a tennis court, making it a perfect choice for those seeking a relaxing and active holiday.

Frequently asked questions about holiday rentals in Radda in Chianti

  • What are some interesting places to visit in or near Radda in Chianti?

    Radda in Chianti is a beautiful town with a rich history. You can visit the Castello di Radda, which dates back to the 11th century and offers stunning views of the Chianti region. The Museo del Vino e dell'Olio is a great place to learn about the local wine and olive oil production. For stunning views of the surrounding countryside, head to the Sanctuary of Santa Maria in Prato.
  • What are the best Airbnb and holiday rentals in Radda in Chianti?

    Castello Di Volpaia, Relais Santa Cristina and Villa Sant’uberto Country Inn are among the best Airbnb and holiday rentals in Radda in Chianti.

  • Which walking or cycling routes are the best in Radda in Chianti?

    The Chianti Classico Wine Trail is a popular cycling route that passes through vineyards and charming villages. The trail is about 130km long and can be done in stages. For walking, the Sentiero degli Dei, or Path of the Gods, is a breathtaking hike that offers panoramic views of the Tuscan countryside.
  • What are the most popular Airbnbs in Radda in Chianti?

  • What sports or outdoor activites can visitors enjoy in and around Radda in Chianti?

    The area is perfect for outdoor enthusiasts. You can go hiking, cycling, and horseback riding in the surrounding hills. There are also several tennis courts and a golf course nearby. For a more relaxing experience, you can go for a swim in one of the many natural swimming pools in the region.
  • What are the best holiday rentals with a pool in Radda in Chianti?

    Castello Di Volpaia, Relais Santa Cristina and Villa Sant’uberto Country Inn are the best holiday rentals with a pool in Radda in Chianti.

  • What other towns or cities can be easily accessed from Radda in Chianti?

    Radda in Chianti is well-connected to other towns and cities in Tuscany. You can easily visit Siena, Florence, and San Gimignano by car or public transport. These towns offer a wealth of historical and cultural attractions.
  • What are the best rentals for families and kids in Radda in Chianti?

    The best rentals for families and kids in Radda in Chianti are Castello Di Volpaia, Relais Santa Cristina and Villa Sant’uberto Country Inn.

  • What amenities are commonly available in vacation rentals in Radda in Chianti?

    Vacation rentals in Radda in Chianti usually come equipped with kitchens, bathrooms, and bedrooms. Many also have private gardens, swimming pools, and outdoor dining areas. Some rentals even offer Wi-Fi and satellite TV.
  • What are the best rentals or Airbnbs with a jacuzzi in Radda in Chianti?

    The best holiday rentals or Airbnb with a jacuzzi in Radda in Chianti are Relais Santa Cristina, In The Heart Of Chianti: View Over The Valley - Relaxation & Art - Wine & Sun and Casa Colle Petroso.

  • What time of year is best to rent a vacation rental Radda in Chianti?

    The best time to visit Radda in Chianti is during the spring or autumn. The weather is pleasant and the crowds are smaller. The summer months can be hot and crowded, while the winter months can be cold and wet.
  • What are the local dishes in Radda in Chianti region?

    Radda in Chianti is known for its delicious cuisine. Try the traditional dishes like Ribollita, a hearty bread soup, and Pici al Ragù, a pasta dish with a rich meat sauce. Don't forget to sample the local Chianti Classico wine, which is produced in the region.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Radda in Chianti

Choosing a holiday rental in Radda in Chianti with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

Casa Di Patti - Radda in Chianti
9.6 26 reviews
Radda in Chianti
05/09 – 19/09
£124/nighttotal: £1736 (14 )

Casa Di Patti

1 2
apartment , Cavriglia
Casa di Patti, situated in Meleto, a short drive from Cavriglia and approximately 21 kilometres from The Mall Luxury Outlet and 24 kilometres from Piazza Matteotti in Arezzo, offers a peaceful Tuscan countryside escape.
This recently renovated one-bedroom apartment, boasting 60 square metres of floor space, sleeps up to nine guests and includes a fully equipped kitchen, air conditioning, Wi-Fi, parking, a terrace, and a complimentary breakfast.
55 M² House ∙ 2 Bedrooms ∙ 4 Guests - Radda in Chianti
9.7 25 reviews
Radda in Chianti
27/06 – 04/07
£135/nighttotal: £945 (7 )

55 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Radda in Chianti
This renovated three-room cottage, offering 55 square meters of living space, is located on the ground floor, approximately 50 meters from the main house, providing a cosy base for exploring Radda in Chianti. The dwelling accommodates up to four guests and features two double bedrooms, a kitchenette, an open-hearth fireplace, WiFi, and a garden, with pets welcome.
200 M² Villa ∙ 5 Bedrooms ∙ 11 Guests - Radda in Chianti
8.8 4 reviews
Radda in Chianti
11/09 – 14/09
£397/nighttotal: £1191 (3 )

200 M² Villa ∙ 5 Bedrooms ∙ 11 Guests

5 3
house , Radda in Chianti
Villa La Petrosa, a 200 square metre, five-bedroom farmhouse in Radda in Chianti, offers easy access to the Chianti Classico wine region and its cultural attractions.
This pet-friendly property boasts a private pool, extensive gardens, three bathrooms, and can comfortably accommodate up to eleven guests, featuring a well-equipped kitchen and multiple balconies.
Uva - Radda in Chianti
Radda in Chianti
27/06 – 04/07
£129/nighttotal: £903 (7 )

Uva

2 2
house , Radda in Chianti
This Radda in Chianti holiday home, named Uva, is situated 18km from Piazza Matteotti and 37km from Piazza del Campo, offering easy access to Tuscan attractions.
The 80 square metre property boasts two bedrooms, one bathroom, a fully equipped kitchen, a swimming pool, and parking, comfortably accommodating up to seven guests.

Find the Best Dog-Friendly Self-Catering Rentals in Radda in Chianti

A quality pet-friendly holiday rental and Airbnb in Radda in Chianti offers city walks on the doorstep without compromising on your comfort. Start comparing our top picks now.

Limoni - Radda in Chianti
10 1 review
Radda in Chianti
27/06 – 04/07
£147/nighttotal: £1029 (7 )

Limoni

2 2
house , Radda in Chianti
Limoni, a holiday home in Radda in Chianti, is situated 18km from Piazza Matteotti and 37km from Piazza del Campo, offering easy access to major Tuscan landmarks.
This 80 square metre property boasts a two-bedroom layout sleeping seven, complete with two bathrooms, a fully equipped kitchen including a dishwasher, Wi-Fi, private parking, a swimming pool, and a terrace; perfect for families or groups exploring the Chianti region.
Apartment Laura By Interhome - Radda in Chianti
8.0 1 review
Radda in Chianti
11/09 – 14/09
£186/nighttotal: £558 (3 )

Apartment Laura By Interhome

2 3
apartment , Greve in Chianti
This Greve in Chianti apartment, situated in a peaceful rural setting within 15km of Castello di Albola, the Franciscan Monastery of St Francis, and the Wine Museum, offers easy access to Chianti Classico's key attractions.
The 140 square metre property boasts two bedrooms, three bathrooms, sleeps seven guests, and includes a swimming pool, garden, parking, Wi-Fi, and a fully equipped kitchen with dishwasher and fridge.
Guest House Il Gatto - Radda in Chianti
8.3 36 reviews
Radda in Chianti
27/06 – 04/07
£91/nighttotal: £637 (7 )

Guest House Il Gatto

2 2
house , Radda in Chianti
Guest House il Gatto, situated in Gaiole in Chianti, is a short drive (34km) from Siena and 60km from Florence, offering easy access to the Tuscan countryside and its attractions.
This 75 square metre property features two bedrooms, one bathroom, a fully equipped kitchen, terrace, garden, tennis court, free parking, Wi-Fi, and barbecue facilities, sleeping up to four guests and providing a peaceful retreat in the Chianti region.
Colombaio Di Cencio - Radda in Chianti
8.5 84 reviews
Radda in Chianti
05/09 – 19/09
£137/nighttotal: £1918 (14 )

Colombaio Di Cencio

1 2
apartment , Gaiole in Chianti
Colombaio di Cencio apartments in Gaiole in Chianti offer Tuscan-style accommodation with hill views, situated amongst vineyards, 31km from Greve in Chianti and a 30-minute drive from Siena.
These family-friendly self-catering apartments boast a swimming pool, garden with barbecue, on-site wine tasting, free parking, and are well-placed for day trips to Florence (approx. 1-hour drive).
©2026 cozycozy.com