Holiday rentals in Gaiole in Chianti

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Tuscany Country House, Central Chianti, Pano Views

Tour (no spaces) www. escapetochianti. com/experience Perfect central base in Tuscany! The Farmhouse at Vignale has spectacular views overlooking organic vineyards in the heart of Chianti Classico wine country. Our spacious, historic artist-inspired stone house has 3 bedrooms, 1 bath (add 1bd/1ba extra fee) large living room, massive fireplace & great kitchen. Minutes to top restaurants & Chianti hill towns; easy drive to Florence & Siena; an ideal location for day trips to all parts of Tuscany

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Charming estate with views. A/C in the bedrooms

The estate finely restored in 2016 is accessorized with all the confort you need for an holiday dedicated to the relax or to excursions The Breathtaking view on the Chianti Classico's vineyards give to the estate a unique feature perfect for a romantic holiday, small group of friend or a little family. The estate is provided of external Jacuzzi, private garden and we can arrange for you bike or hike excursions. The Village of Gaiole in Chianti is just 5 minutes away by car.

Villa Eroica

A charming house in the heart of Chianti Located at the entrance to the picturesque municipality of Gaiole in Chianti, this beautiful house offers a quiet and strategic location, a short walk from the center of the village. Ideal for those seeking relaxation and convenience, combining elegance and comfort. Experience having a home in the heart of Tuscany surrounded by a magnificent garden largely for exclusive use and with a large swimming pool shared with adjacent units.

The Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Sestuccina

Sestuccia Cantina is romantic cottage with two double bedrooms and sofa bed in the living room. The villa is located a few kilometers from Gaiole in Chianti and is surrounded by vineyards, with incredible views of Orchard Castle, The villa is completely built in stone with a beautiful shaded terrace. Guests have access to a relaxing bar area with heated Jacuzzi for 6 persons. Inside the park there is a Chicken Coop with fresh eggs every morning and organic garden.

Independent cottage surrounded by nature

The Cottage is located inside the Tiorcia farm, less than 4 km from Gaiole in Chianti, a village of the Eroica, surrounded by woods and overlooking the hills of Chianti Senese. The property consists of a spacious living room, kitchenette and bathroom with shower. A distinctive feature of the house is the mezzanine with a double bed; there is also the possibility of using a small sofa bed. The accommodation is ideal for a couple or a family with one/two children

Casa Dante – Authentic Chianti Stay | Views & Relaxation

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.