Compare villa rentals in Radda in Chianti from 100+ providers!

The semi-detached house, 'Ridaldi', is located in Greve in Chianti, offering a rustic retreat with convenient access to local attractions within the renowned Chianti Classico wine region.
This 1830 square foot villa accommodates up to 8 guests across 4 bedrooms and 4 bathrooms, featuring air conditioning, a swimming pool, jacuzzi, garden with barbecue, and free WiFi.

This five-bedroom villa in Radda in Chianti, Tuscany, is located two miles from Castello di Albola and 2.5 miles from Castello di Radda Winery, offering easy access to renowned Chianti Classico wineries.
The 9690-square-foot (approximately 900-square-meter) property features a private pool, fitness center, sauna, and spa, accommodating large families or groups with a fully equipped kitchen, Wi-Fi, and ample outdoor space including a terrace and garden.

This family-friendly farm stay is located just six miles from the historic center of Castellina in Chianti, offering a peaceful escape from the town's bustle while still being close to its attractions. Guests have consistently rated the property excellent for its cleanliness, location, and overall experience.
The rental features a fully equipped kitchen with a fridge and dishwasher, as well as air conditioning, a private terrace, and a garden. Enjoy the outdoor pool, barbecue grills, and the surrounding countryside, perfect for relaxing and exploring the Chianti region.

This house in Cavriglia is 17 miles from The Mall Luxury Outlet and 29 miles from Piazza della Signoria.
This 1080 sq ft home offers 2 bedrooms, 1 bathroom, and accommodates up to 11 guests with a private pool, free WiFi, air conditioning, and a fully equipped kitchen.

Tenuta il Poggetto is a country house set amidst rolling hills, vineyards, and olive groves, 13 miles from the charming town of Radda in Chianti. It offers a serene escape for nature lovers and those seeking relaxation, while also being conveniently located for exploring the region.
The house has excellent user and location ratings and features generously sized rooms with comfortable seating areas, fully equipped kitchens, and private bathrooms. Guests can enjoy the stunning surroundings on the property's terrace, which offers panoramic views of the Tuscan landscape. The house also offers a range of activities, including darts, walking tours, and a picnic area, as well as modern amenities such as free Wi-Fi, cable flat-screen TVs, and fully equipped kitchens.

This farm stay in Gaiole in Chianti is centrally located in the Chianti Classico region, offering an immersive medieval Italian experience near Lecchi in Chianti, Meleto Castle, and Castle of Brolio.
The 1720 square foot property features 4 bedrooms and 3 bathrooms, accommodating up to 12 guests with amenities including a kitchen with a fridge, microwave, and dishwasher, a swimming pool, and a garden, with opportunities for local cuisine cooking classes.

L'arco della Fonte, located in Gaiole in Chianti, offers easy access to local amenities and public transportation.
This 93-square-meter house features two bedrooms, one bathroom, and accommodates four guests, boasting a fully equipped kitchen, private garden with terrace and barbecue, high-speed Wi-Fi, on-site parking, and even an in-house gym; plus, enjoy wine, vinsanto, grappa, and olive oil EVO tastings produced on the property.

This five-bedroom, five-bathroom villa, Solaria di Santa Maddalena 10, is situated in Castelnuovo Berardenga, Tuscany, approximately 10 miles from Siena's Piazza del Campo and 18 miles from Grosseto's Piazza Matteotti.
The spacious property boasts a fully equipped kitchen, private balcony, free Wi-Fi, free parking, a swimming pool, and a garden, perfect for families or large groups seeking a relaxing Tuscan getaway.

Villa Castiglioni, a luxurious Tuscan estate, is located 2.5 miles from Radda in Chianti, near Castello di Albola and Castello di Radda Winery, offering easy access to Greve in Chianti and Siena.
This five-bedroom, seven-bathroom villa sleeps up to 11 guests and boasts a private heated pool (May-September), a jacuzzi, sauna, spa, fitness center, and 5 hours of daily maid service (excluding Sundays), plus a fully equipped kitchen and extensive grounds with barbecue and playground.

Casa Valerian, a one-bedroom apartment in Castellina in Chianti, is a short distance from the town center and offers panoramic views of vineyards, olive groves, and woodlands.
The apartment features a fully equipped kitchen with a stove, oven, fridge, and other essentials, a garden, and can accommodate up to two guests.

This 16th-century Tuscan farmhouse rental in Crognole, 3 miles from Radda in Chianti and 1.2 miles from Castello di Albola, boasts stunning panoramic views of the Chianti hills.
This 1370-square-foot villa features three bedrooms, three bathrooms, a private pool (open late April to early October), and accommodates six guests, with amenities including a fully equipped kitchen, Wi-Fi, and air conditioning.

La Campesa, located in Vagliagli, offers a secluded country house experience 8.7 miles from Siena's Piazza del Campo, providing easy access to other Tuscan destinations.
This 650-square-foot (approximately 60-square-meter) vacation rental boasts two bedrooms, one bathroom, and accommodates four guests, featuring a Jacuzzi, garden, free Wi-Fi, parking, and complimentary welcome amenities.

Il Fico in Chianti, a spacious vacation home, is located 15 miles from Piazza Matteotti in Gaiole in Chianti, offering easy access to both the town and attractions like Piazza del Campo (19 miles) and The Mall Luxury Outlet (22 miles).
This 1610-square-foot house features 3 bedrooms, 2 living rooms, a swimming pool, a garden, and accommodates up to 11 guests, with amenities including a fully equipped kitchen, free Wi-Fi, and free private parking.

This Radda in Chianti villa, situated just 1.5 miles from the village, offers panoramic vineyard views and easy access to landmarks like Castello di Albola and Castello di Radda Winery, with Florence and Siena within driving distance.
This estate accommodates up to 9 guests in 4 bedrooms and 5 bathrooms, featuring a heated 39x16 foot swimming pool, a wellness center with a Turkish bath and sauna, on-site cooking lessons, and wine tastings, plus an EV recharge point.

Casa della fonte-Chianti is a 2-bedroom house located in Gaiole in Chianti, 19 miles from Piazza del Campo and 25 miles from Piazza Matteotti.
This 700 sq ft villa accommodates up to 11 guests, featuring a well-equipped kitchen, a fireplace, a terrace with mountain views, a garden, a swimming pool, a hot tub (closed April 19, 2027 - October 18, 2026), and complimentary Wi-Fi and parking.

This family-friendly farmhouse rental near Radda in Chianti, Italy is conveniently located 3 miles from Castello di Radda Winery and within 6 miles of Pieve di San Leolino and the Church of Santa Maria Assunta.
This 1120-square-foot vacation home boasts two bedrooms, two bathrooms, a private pool, jacuzzi, fitness center, and a fully equipped kitchen including a dishwasher, all within a beautifully maintained garden with barbecue grills and on-site water park.