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Villa Luigi – A Majestic Restored Farmhouse with Wellness Spa

chianti holiday rentals outdoor pool area

Villa Luigi is a fabulous choice for travelers seeking chianti holiday rentals that combine privacy, elegance, and access to world-class amenities. It sits in the rolling Tuscan hills within 740-acre estate. This restored 18th-century farmhouse exudes traditional charm with modern luxury. Moreover, it offers panoramic countryside views, outstanding services, and easy access to Florence and […]

Luxury Eco Chianti Holiday Villa – Villa Belvedere Oasis

chianti holiday villa pool

Slow Living in Chianti Villa Belvedere is where simplicity and the power of nature reign. Cradled between Florence and Siena, this chianti holiday villa invites you to slow down and tune in to nature’s rhythm. Spanning 50 hectares, it’s a mini utopia where regenerative and permaculture farming thrives, inspired by pioneers like Masanobu Fukuoka and […]

Il Mulino Dell’Abate: Villa in Chianti with Riverside Charm

Villa in Chianti Outdoor Pool

Il Mulino Dell’Abate (“Mill of the Abbot”) is a charming historic villa in Chianti, located in Tavarnelle Val di Pesa between Florence and Siena. Originally a historic mill, this beautifully restored property blends modern amenities with rustic Tuscan charm. The villa sits along the peaceful Pesa River, surrounded by lush gardens, olive trees, and rolling […]

Casolese di Vignamaggio – Greve in Chianti Villa Rental

Greve in Chianti Villa Rental - aerial

The allure of Tuscany lies in its rich tapestry of art, culture, and history, where every corner seems to be touched by a thousand years of fascinating stories. Among its many storied properties, the Vignamaggio estate stands out as one of the most intriguing. This historic estate was once the family home of the noble […]

Molino del Chianti – Villa with Heated Swimming Pool

villa il molino outdoor white flowers

The phenomenal air-conditioned five-bedroom Villa il Molino del Chianti is a lovingly renovated, gorgeous modern villa with an open floor plan, located just a short drive from Siena. This outstanding 320-square meter home is built on two stories and charming blends beautiful Tuscan antiques with modern conveniences to produce the perfect vacation for its lucky […]

la Veduta di Vertine – Staffed Villa in Gaiole Chianti

Luxury Villa in Gaiole in Chianti - Poolside

La Veduta di Vertine is a stunning luxury villa in Gaiole in Chianti. It is a five-bedroom, air-conditioned with swimming pool located in the heart of Chianti, within walking distance of the charming town of Gaiole – recently named “The Most Idylic Place to live in Europe” by Forbes magazine. This spectacular, immaculately restored 16th […]

Premium Wine Estate Villa – 7 bedroom with AC

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If you have ever wondered what it is to live on a premium vineyard estate, the luxurious seven bedroom air conditioned Villa Capannelle is the perfect place for your holiday! Located in the heart of Chianti Classico this estate presides over some of the best vineyards of all of Tuscany! Located within walking distance to the […]

Villa Pianora – 6 bedroom Tuscany Villa

villa Pianora Pool Jacuzzi

Villa Pianora is an ancient semi-detached villa nestled amongst the vineyards and olive groves of the Elsa valley. It has been recently restored and equipped with any comfort you may need make which makes it perfect place for a relaxing getaway. The property’s rustic stone-walled exteriors have a lovely charm to spare. Rich in history, and sleeping […]

Rent Italy’s Finest Luxury Villas in Chianti Tuscany: Sleeps 12

Villa la fornace aerial view

Villa La Fornace is a luxury villa in Chianti for rent with six bedrooms offering the lucky guest a phenomenal vacation. Perfectly situated in Tavarnelle Val di Pesa, less than half an hour from both Florence and Siena and adjacent to Castello Nero, this newly renovated 17th Century villa features clean architectural lines, modern furniture, […]

Castellare, 7 bedroom Chianti Air Conditioned Villa

chianti villa 7 bedroom with AC

Castellare is a recently renovated (in 2016) 7 bedroom Chianti air-conditioned villa, an oasis of Tuscan charm located in the quaint village of Palazzuolo just outside of Tavarnelle in Chianti, 40 minutes south of the city of Florence and 40 minutes from the city of Siena. Adjacent to the one-thousand-year-old church of Sant Bartolomeo, this […]

Villa il Prato, Chianti Villa Rental

Chianti Villa Rental - Villa il Prato view

Villa il Prato is a phenomenal air conditioned 11 bedroom Chianti villa rental located just outside the picturesque town of Greve in Chianti, about 40 minutes from the city of Florence. This fantastic staffed mansion traces its origins back one thousand years when a tower was erected on the site, and probably was first used […]

Modern Luxury Villa in Chianti for Rent [Villa Torre il Santo]

villa torre il santo pool with sunbeds

Villa Torre il Santo is a newly renovated eight bedroom air-conditioned modern luxury villa located overlooking the UNESCO world heritage site of San Gimignano. Originally built in 1,000 A.D., this spectacular villa was meticulously restored in 2013 using its original stones and beams to create a bright and luminous home with architecturally clean lines and […]

Sole Del Chianti – Tuscan Villa With Spa & Vineyard

Sole Del Chianti pool

The charming Villa Sole del Chianti is a nine-bedroom + 2 bedroom in the annex air-conditioned Tuscan villa with spa and vineyard nestled in the lush vineyards of Chianti just outside the picturesque town of Tavarnelle Val di Pesa, in close proximity to both Florence and Siena. Built in the early 19th century, this elegant […]

Casa Fabbri, Villa with Horseback Riding Nearby

Casa Fabbri Horseback villa with pool Outside Lounge

Imagine yourself in a villa with horseback riding nearby. The place is just 20 minutes from Siena and less than an hour south of Florence in a magnificent 12th-century tower on top of a hill and looks down at a 360-degree panoramic view of vineyards and olive trees. Here you can watch deer and wild goats […]

Villa Il Palagio, Sting’s Estate in Tuscany

Villa Palagio Facade

Sting’s villa in Tuscany, the magnificent il Palagio Estate may be one of the most fabulous villas and estates we have visited in Tuscany! This stellar air conditioned nine bedroom 16th Century villa is owned, and often inhabited, by rock and roll icon, Sting and his wife movie producer, Trudie Styler and features spectacular and […]

Rent Chianti Villa with Private Pool

Borgo Gerlino swimming pool

Borgo Gerlino is a delightful 9 bedroom chianti villa with pool situated in a hills top position, between the provinces of Siena and Arezzo, just outside the picturesque villages of Ambra & Montebenichi. Tracing its origins back to the Middle Ages, this Chianti villa with pool was recently rebuilt to create a luxurious and comfortable mansion […]

Villa Spino, Yoga Retreat Villa

villa spino yoga retreat in tuscany

Amidst the award-winning vineyards of Chianti’s fertile Val d’Ambra region, the magnificent ten-bedroom 16th Century Villa Spino is one of the most elegant and beautifully furnished large villas in the region. It is a villa of historical importance – it was built by the Medici family, the family that financed and inspired the Renaissance. This […]

Villa Felciai, Authentic Tuscany

villa felciai exterior

If your idea of a perfect holiday is a villa located in the middle of a fabulous vineyard producing some of the finest Chianti and Supertuscan wines in the world, then Villa Felciai and its twin sister villa, Casa Fabbri located two hundred meters away, are two of the best ways to experience what we […]

il Borgo – Holiday Villa in Tuscany

il borgo pool side

Villa il Borgo is one of the most ideal villa for family reunions among our the large holiday villas in Tuscany. Its stellar 15 air-conditioned bedrooms and location, perfectly nestled in the Chianti countryside, less than 20 minutes south of Florence, make it the perfect fit for large groups. This luxury villa was beautifully renovated in 2012. […]