Chianti Villas & Luxury Vacation Rentals

Your Guide to Chianti Luxury Villas

Located in the heart of Tuscany between Florence and Siena, Chianti is one of the most celebrated wine regions in the world. Rolling vineyards, cypress-lined ridges, and stone hamlets define its landscape, while centuries of winemaking tradition shape its identity.

Viticulture here dates back to the Etruscans and Romans, and during the Renaissance, the Medici family formalized the region’s reputation, investing in estates and promoting Chianti wines across Europe. Today, the Chianti Classico designation reflects strict production standards and a continued commitment to quality.

Chianti villa rentals allow you to experience this heritage from within the countryside itself. Rather than visiting for a tasting or day trip, you wake among vineyards, dine outdoors overlooking olive groves, and return each evening to your own private estate.

Rental Escapes curates a collection of Chianti villas selected for their architectural character, panoramic settings, and service level, offering a refined base for exploring one of Tuscany’s most iconic regions within Italy.

Chianti Villa Rentals

Like the region itself, Chianti estates are steeped in history. Restored farmhouses with stone walls, terracotta roofs, and expansive terraces are common throughout the countryside. At the same time, many properties incorporate modern amenities such as heated pools, private gyms, gourmet kitchens, and full staff support.

Villas are spread across the region’s most desirable villages, including Greve, often considered the gateway to Chianti; Panzano, known for its culinary reputation; Castellina, with its Etruscan roots; Radda, encircled by medieval walls; and Radicondoli, a serene hilltop retreat.

Wherever you stay, panoramic vineyard views and fresh countryside air define the experience. Dedicated Concierge service ensures each stay is both seamless and personalized.

Luxury Villas in Chianti

Chianti is synonymous with fine wine, exceptional cuisine, and sweeping landscapes. Luxury villas in Chianti place you directly within this setting, offering stays that balance historic character with modern refinement. Featured estates include:

Vinia: A recently restored farmhouse, Vinia offers an elevated rustic experience in the heart of Chianti. With a modern interior and features like a unique pool, a large outdoor dining area, and a covered fireplace, Vinia has everything you need for the ultimate Tuscan holiday.

Castellare de‘ Sernigi: A true family villa that has been passed down through the generations, Castellare de’ Sernigi evokes a timeless beauty thanks to its many unique touches. A swimming pool surrounded by a stone terrace. Centuries-old cypress trees. Authentic artwork throughout. You’ll find it all here.

Leonardo: A spacious country home, Leonardo has been restored inside and out to create a simple elegance. Take a dip in the pool. Enjoy a meal al fresco. Admire the stunning views. This is Tuscan living.

Montosca: A ten-bedroom Chianti estate designed to accommodate extended families and large groups comfortably, with space for twenty guests across the main villa, a guest house, and an independent annex. The layout gives families natural separation while keeping everyone connected through shared spaces like the infinity pool and outdoor dining areas.

Chianti Villas with Pools

The Tuscan climate brings Chianti to life in the warmer months. A private pool becomes the focal point of a countryside stay, whether for long afternoons overlooking vineyards or evening swims beneath open skies. Featured villas include:

Trionfante: A traditional Tuscan villa surrounded by a verdant Mediterranean garden, Trionfante is the perfect place to relax and take in the Tuscan sun. It’s also just a short drive to the village of Sambuca, where you can enjoy narrow streets, stone buildings, and an authentic Tuscan atmosphere.

Verdiana: Nestled along vineyards and olive trees, Verdiana offers a dreamy atmosphere. It combines rustic surfaces with plush furnishings for comfort, while the swimming pool, gym, and Turkish bath promise further renewal. A great choice for wine lovers.

Fleda: Spread across twenty acres of vineyards and olive groves, Fleda offers outdoor spaces that pull you outside from breakfast through dinner. The property includes a heated pool, outdoor dining terrace, sauna, and multiple lounging areas scattered through gardens where ancient olive trees provide shade between wine tastings. A tower bedroom offers 360-degree countryside views, while ground-floor rooms open directly to the gardens, making it easy to move between indoor and outdoor living throughout the day.

Davinia: Set between Greve and Panzano, Davinia is composed of three separate buildings brought together by communal spaces. It’s all punctuated by panoramic views of the surrounding valleys and vineyards, including from the terraced swimming pool. A great choice for groups traveling together.

Chianti Villas FAQ

Book a Chianti Villa with Rental Escapes

Our curated collection of Chianti villa rentals includes restored stone farmhouses, expansive vineyard estates, and panoramic countryside retreats set between Florence and Siena. Each residence is selected for its architectural character, setting, and level of service within our broader portfolio of villas in Tuscany and villas in Italy.

Your Villa Specialist will guide you in selecting the right estate based on your group size, preferred village or vineyard setting, and desired amenities. After booking, your Concierge can arrange private wine tastings, chef service, vineyard tours, airport transfers, and curated countryside experiences throughout Chianti.

Chianti offers a slower rhythm, defined by vineyards, stone villages, and open horizons. The right villa transforms your stay from a visit into a fully immersive Tuscan experience.

Contact a Villa Specialist to begin planning your Chianti villa stay.