Search Radda in Chianti villas and holiday homes

663 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Radda in Chianti villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

663 Villa rentals in Radda in Chianti

Best Radda in Chianti villas and holiday homes with a pool

Among the 663 accommodations in Radda in Chianti, here are the 4 best villas and holiday homes with a pool

La Petrosa - Radda in Chianti
8.0 2 reviews
Radda in Chianti
11/09 – 14/09
A$906/nighttotal: A$2718 (3 )

La Petrosa

5 3
house , Radda in Chianti
La Petrosa, in Radda in Chianti, is ideally located 22.5km from Piazza Matteotti and 27.4km from Piazza del Campo, offering easy access to Tuscany's key landmarks.
This 200 square metre property sleeps 22 guests and boasts five bedrooms, a private swimming pool, a terrace, a garden, parking, and a fully equipped kitchen including a dishwasher; barbecue facilities are also available.
Il Poderino - Radda in Chianti
9.6 203 reviews
Radda in Chianti
27/06 – 04/07
A$257/nighttotal: A$1799 (7 )

Il Poderino

1 2
farm , Castellina in Chianti
Il Poderino is a farmhouse located in Monteriggioni, Tuscany, 19 kilometres from Siena and 50 kilometres from Florence.
The property offers a seasonal outdoor pool, a barbecue terrace and private gardens for each apartment, as well as wine tasting tours and the opportunity to sample homemade grappa, honey and wine.
70 M² House ∙ 2 Bedrooms ∙ 6 Guests - Radda in Chianti
10 2 reviews
Radda in Chianti
27/06 – 04/07
A$174/nighttotal: A$1218 (7 )

70 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Gaiole in Chianti
This apartment, 'Montechioccioli', is located in the Tuscan countryside, offering panoramic views and easy access to the historic town of Gaiole in Chianti.
This 70 square meter cottage accommodates up to 6 guests, featuring 2 bedrooms, 1 bathroom, air conditioning, Wi-Fi, a dishwasher, and a swimming pool, with private parking for 2 cars.
Holiday Home Le Bonatte By Interhome - Radda in Chianti
10 42 reviews
Radda in Chianti
27/06 – 04/07
A$256/nighttotal: A$1792 (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.

Best family friendly Radda in Chianti villas and holiday homes

Among the 663 accommodations in Radda in Chianti, here are the 4 best family friendly villas and holiday homes

Ancient House In Chianti Hills With Private Lake And Garden - Radda in Chianti
10 5 reviews
Radda in Chianti
27/06 – 04/07
A$238/nighttotal: A$1666 (7 )

Ancient House In Chianti Hills With Private Lake And Garden

2 2
farm , Radda in Chianti
This charming farmhouse is situated just 5km from the Il Molino di Grace Winery and the historic Borgo di Vescine, offering a tranquil escape in the heart of the Chianti region. It has received excellent reviews from previous guests.
The property spans 64 square metres and comfortably accommodates up to 4 guests in its 2 bedrooms. The farm stay offers a range of amenities, including a swimming pool, fitness centre, and a garden with barbecue facilities, perfect for enjoying the beautiful Italian weather.
Farmhouse In The Chianti "La Foresta 1" With Swimming Pool - Radda in Chianti
9.0 42 reviews
Radda in Chianti
11/09 – 14/09
A$287/nighttotal: A$861 (3 )

Farmhouse In The Chianti "La Foresta 1" With Swimming Pool

1 3
farm , Castellina in Chianti
This family-friendly farmhouse is located just 10 kilometres from Castellina in Chianti's City Hall, Castellina Fortress, and the Walls of Monteriggioni, offering a peaceful escape in the Tuscan countryside. The property has received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse offers a range of amenities to ensure a comfortable stay, including a kitchen equipped with a fridge and dishwasher, air conditioning, a swimming pool, a terrace, a garden, and parking. Guests can enjoy relaxing in the garden, taking a dip in the pool, or grilling a meal outdoors.
Casa Colle Petroso - Radda in Chianti
9.7 117 reviews
Radda in Chianti
27/06 – 04/07
A$955/nighttotal: A$6685 (7 )

Casa Colle Petroso

4 2
house , Radda in Chianti
Casa Colle Petroso is a charming villa located in the Chianti countryside, just 22.5 km from the town centre of Radda in Chianti and 27.3 km from Siena's Piazza del Campo. This property has received excellent ratings for location, cleanliness and overall experience.
The villa has 4 bedrooms and a fully equipped kitchen. Enjoy the private pool, hot tub, terrace, garden, barbecue facilities, restaurant and free parking, making it a perfect choice for a relaxing getaway.
Farmhouse In Chianti - Radda in Chianti
9.8 6 reviews
Radda in Chianti
11/09 – 14/09
A$936/nighttotal: A$2808 (3 )

Farmhouse In Chianti

4 3
farm , Gaiole in Chianti
This agriturismo in Lecchi in Chianti, within the Chianti Classico region, offers an immersive medieval Italian experience within 5 kilometers of Castello di Meleto and Castello di Brolio.
This family-friendly farm stay, spanning 160 square meters and accommodating up to 12 guests, features 4 bedrooms, 3 bathrooms, a kitchen with a fridge, microwave, and dishwasher, a swimming pool, a garden, and on-site cooking classes focusing on local cuisine, with breakfasts and dinners provided by the hosts.

Frequently asked questions about villa rentals in Radda in Chianti

  • What are the must-see attractions in and around Radda in Chianti?

    Radda in Chianti is a beautiful medieval town, and you must visit the imposing Rocca di Radda, the main square, Piazza Salvadori, and the church of San Niccolò. You should also take a day trip to the nearby town of Siena, which is about a 40-minute drive away.
  • What are the best villa rentals in Radda in Chianti?

    Among the villa rentals in Radda in Chianti, Castello Di Volpaia, Villa Sant’uberto Country Inn and Relais Santa Cristina are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Radda in Chianti?

    You're likely to see lots of birds, such as the Eurasian Sparrowhawk, the European Robin, and the Eurasian Jay. You'll also see deer, wild boar, and hares in the surrounding countryside.
  • What are the best villa rentals with a pool in Radda in Chianti?

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

  • What is the best time to visit Radda in Chianti?

    The best time to visit Radda in Chianti is during the spring (April-May) or autumn (September-October) when the weather is pleasant and the crowds are smaller. The summer months (June-August) are hot and busy, and the winter months (November-March) can be cold and wet.
  • What are the best villa rentals with a jacuzzi in Radda in Chianti?

  • When is it easiest to book a villa rental in Radda in Chianti?

    The easiest time to book a villa rental in Radda in Chianti is during the shoulder seasons (April-May and September-October) when demand is lower and prices are more affordable. You can often get good deals by booking several months in advance.
  • What are the best villa rentals for families and kids in Radda in Chianti?

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

  • What are the top hiking trails near Radda in Chianti?

    There are many great hiking trails in the area, but some of the most popular are the Sentiero degli Dei (Path of the Gods), the Via Francigena, and the Chianti Classico Trail. These trails offer stunning views of the rolling hills and vineyards.
  • What are the best pet friendly villa rentals in Radda in Chianti?

    The best pet friendly villa rentals in Radda in Chianti are Castello Di Volpaia, Relais Santa Cristina and Tuscany House "La Querce Sola".

  • What are the advantages of renting a house or a villa in Radda in Chianti

    Renting a villa in Radda in Chianti gives you more privacy and space than staying in a hotel. You can enjoy your own private pool, garden, and kitchen, and you can cook your own meals. It's also a great way to experience the local culture and way of life.
  • What are the best villa rentals with parking in Radda in Chianti?

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

  • Are there popular destinations near Radda in Chianti?

    Yes, there are many popular destinations near Radda in Chianti, including Florence, Siena, and San Gimignano. You can easily take a day trip to any of these places from Radda in Chianti.

Destinations nearby

Best Radda in Chianti villas and holiday homes with parking

Podere Terreno Alla Via Della Volpaia - Radda in Chianti
9.6 321 reviews
Radda in Chianti
27/06 – 04/07
A$339/nighttotal: A$2373 (7 )

Podere Terreno Alla Via Della Volpaia

1 2
farm , Radda in Chianti
Podere Terreno alla via della volpaia is a farm stay located in Radda in Chianti, 21 kilometres from Siena and 58 kilometres from Florence, offering a peaceful retreat in the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The farm stay features a shared lounge and garden, perfect for relaxing after a day of exploring the region. Guests can enjoy a range of breakfast options, take advantage of the on-site spa, and enjoy cycling trails in the surrounding area.
Villa Sant’uberto Country Inn - Radda in Chianti
8.2 329 reviews
Radda in Chianti
11/09 – 14/09
A$208/nighttotal: A$624 (3 )

Villa Sant’uberto Country Inn

1 3
house , Radda in Chianti
Villa Sant'Uberto, in the Chianti region near Radda in Chianti, enjoys a hilltop position offering stunning views and is within 0.4km of restaurants.
This one-bedroom, one-bathroom property boasts a swimming pool, terrace, garden, and on-site amenities including a restaurant, bar, and fitness centre, sleeping up to two guests.
Villa Al Bosco: An Elegant And Welcoming Three-story Villa Situated In A Secluded Location Surrounded By Meadows And By Green Hills, With Free Wi-fi. - Radda in Chianti
Radda in Chianti
11/09 – 14/09
A$1923/nighttotal: A$5769 (3 )

Villa Al Bosco: An Elegant And Welcoming Three-story Villa Situated In A Secluded Location Surrounded By Meadows And By Green Hills, With Free Wi-fi.

6 3
house , Radda in Chianti
Villa Al Bosco is a secluded six-bedroom villa located 5.8 kilometres from the centre of Radda in Chianti, close to several restaurants and within easy reach of the Castello di Radda Winery.
This spacious 290 square metre property features a private swimming pool, a large garden with a barbecue, and can accommodate up to twelve guests.
Wonderful  Villa For 12 People With A/c, Wifi, Private Pool, Hot Tub, Tv And Patio - Radda in Chianti
Radda in Chianti
11/09 – 14/09
A$699/nighttotal: A$2097 (3 )

Wonderful Villa For 12 People With A/c, Wifi, Private Pool, Hot Tub, Tv And Patio

6 3
house , Greve in Chianti
This farmhouse is situated in a secluded hilltop position 10 kilometres from Greve In Chianti, offering scenic views and easy access to Panzano (8 kilometres), Radda (12 kilometres), Florence (35 kilometres) and Siena (43 kilometres).
This 290 square metre property across three levels accommodates up to 12 guests in six bedrooms, featuring multiple kitchenettes, six bathrooms, a seasonal swimming pool (May 16 - Oct 3), hot tub, barbecue, garden furniture, and four bicycles.

Best Radda in Chianti villas and holiday homes with a garden

Antica Dimora A Campana - Radda in Chianti
9.9 125 reviews
Radda in Chianti
27/06 – 04/07
A$301/nighttotal: A$2107 (7 )

Antica Dimora A Campana

1 2
house , Greve in Chianti
This three-bedroom, two-bathroom house in Panzano in Chianti, approximately 10-15 minutes' drive (approx. 10-15 km) from Greve in Chianti, offers a private courtyard, garden, and solarium with panoramic views.
The property sleeps six guests and includes a well-equipped kitchen, private parking, and is close to local amenities; one double bedroom even boasts a walk-in wardrobe.
162 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Radda in Chianti
10 21 reviews
Radda in Chianti
11/09 – 14/09
A$473/nighttotal: A$1419 (3 )

162 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

3 3
house , Radda in Chianti
This 17th-century farmhouse, situated in the Chianti Classico region, is a 6km drive from Radda in Chianti and within a 100km radius of Florence, Siena, and Arezzo.
This 162 square metre property offers three bedrooms sleeping six, a well-equipped kitchen, private garden with BBQ, table tennis and badminton, plus free Wi-Fi and air conditioning.
Agriturismo Podere Tegline - Radda in Chianti
9.7 54 reviews
Radda in Chianti
27/06 – 04/07
A$312/nighttotal: A$2184 (7 )

Agriturismo Podere Tegline

2 2
farm , Radda in Chianti
Agriturismo Podere Tegline is located in Radda in Chianti, surrounded by vineyards, just 12 miles from Siena and 15 miles from San Gimignano. This farm stay has excellent user, location, and cleanliness ratings.
Each apartment has a comfortable seating area and a fully equipped kitchen. Enjoy the Tuscan sunshine on the sun terrace, relax in the garden, and take advantage of free Wi-Fi and parking.
Chianti Vineyards Olive Groves Food Tastings Scenic Views - Radda in Chianti
9.2 28 reviews
Radda in Chianti
11/09 – 14/09
A$328/nighttotal: A$984 (3 )

Chianti Vineyards Olive Groves Food Tastings Scenic Views

2 3
farm , Greve in Chianti
This charming gîte is situated in a peaceful rural setting just 5 kilometres from the popular Querciabella and Savignola wineries, as well as the charming Piazza Matteotti and the Wine Museum, making it an ideal base for exploring the beautiful region of Greve in Chianti. The property has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere.
The gîte spans 80 square metres and comfortably accommodates up to 4 guests in its two bedrooms and one bathroom. The property offers a range of amenities including a swimming pool, terrace, garden, fitness centre, and parking, perfect for a relaxing and enjoyable stay.
©2026 cozycozy.com