Chianti Area Holiday Villas, Tuscany
18 br, 22 ba (18 Ensuite)
Hold a family reunion, anniversary party, or wedding Tuscan-style at Villa Gaia. For centuries, Italian noble families celebrated at this eighteen-bedroom villa near Siena in the Chianti region; now, its grand interiors have been restored and offer a luxurious retreat.
7 br, 7 ba (7 Ensuite)
Get a taste of Italy’s aristocratic past and stylish present at Villa Vistarenni in Chianti. The stately seven-bedroom villa dates from the 17th century and has a 16th-century chapel perfect for special events.
6 br, 6 ba (3 Ensuite)
Live out a historic Italian fantasy in the luxurious, newly renovated Villa Palazzo. From its romantic stucco exterior, medieval stone tower and 13th-century chapel and crypt to its traditionally furnished interiors and on-site staff, there’s plenty to inspire and pamper.
10 br, 11 ba (7 Ensuite)
Soak in the Tuscan sun at villa Sole del Chianti. This ten-bedroom farmhouse near Florence dates from the turn of the century but has been recently renovated, with accommodations in both a main house and a separate cottage.
5 br, 5 ba (1 Ensuite)
With vine-covered stone walls and panoramic views of the Chianti countryside, villa Arianna couldn’t be more charming. Not only does this renovated five-bedroom farmhouse have cozy rustic interiors and inviting outdoor spaces, it’s just minutes from the sights of Siena and a short drive from other must-see Tuscan cities and towns.
5 br, 5.5 ba (5 Ensuite)
Set on a hilltop in Chianti, villa Le Pratola offers views in every direction and something for every member of the family. Kids will love the pool and games room, while adults will appreciate the proximity to Siena and Florence.
7 br, 6.5 ba (6 Ensuite)
From the outside, La Maccinaia looks like the well-preserved 17th-century Tuscan villa it is, with three stories of stone walls standing atop a hill in the heart of Chianti. On the inside, though, this seven-bedroom property is an intriguing mix of restored architectural features and modern furnishings, with a stunning kitchen at the center.
6 br, 5.5 ba (4 Ensuite)
Capanna Cerreto is a private country villa nestled in 50 acres of vineyards and woodlands in Chianti. This former hayloft to the Castle of Cerreto has been totally transformed into a luxurious yet relaxed country home by its decorator owner.
7 br, 5 ba (1 Ensuite)
Perfect for a quiet getaway, family reunion or tour of the Chianti Classico region, Il Colombaio is a secluded seven-bedroom farmhouse. Recently restored by an American family, the property features original Tuscan charm and stunning panoramic views as well as modern touches like a pool and spacious terrace.
7 br, 4 ba, Pool
Situated on a hilltop outside the village of Greve in Chianti, Montoro offers expansive views, manicured grounds and elegant, comfortable interiors. This handsome seven-bedroom stone villa was built in the 19th century and recently renovated.
6 br, 5 ba (2 Ensuite)
With its arched doorways, stone exterior and beautifully restored interiors, villa Camporempoli is a charming hideaway. Its secluded location in the hills outside Siena and panoramic views of the Chianti area offer peace and quiet.
6 br, 6 ba (5 Ensuite)
A renovated farmhouse nestled on a private estate, Villa Leonardo charms with cozy interiors and lush garden. The 12 acre grounds provide peace, quiet and spectacular views of the countryside near Montespertoli, in the heart of Chianti, but Florence is just 30 minutes away.
6 br, 5 ba (3 Ensuite), Pool
Whether you’re a connoisseur of wine or simply enjoy a glass with dinner, a stay at La Corte di Campalli in Chianti is an unforgettable experience. Located on a large wine estate, the six-bedroom farmhouse was built in the 16th century and restored in 2002.
5 br, 4 ba (2 Ensuite)
If Chianti doesn’t already mean “wine” to you, it will after you visit Campassole. Though this stone farmhouse has been impeccably restored, you’ll want to spend the day under the pergola or in the pool, gazing at the surrounding vineyards.
6 br, 5 ba (4 Ensuite)
Get a taste of rural Tuscan life at La Pozza di Volpaia. Located in the village of Volpaia, this six-bedroom stone villa is surrounded by a medieval fortified town, but has panoramic views of the countryside.
3 br, 3 ba (3 Ensuite)
Tucked between the villages of Gaiole and Radda in Chianti in the heart of Tuscany, Cavalcanti offers the privacy of a villa and the amenities of a larger estate. As part of the restored hamlet of Castello di San Donato in Perano, the three-bedroom property is surrounded by vineyards, a 10th-century castle and a church, among other historic buildings.