Villa holiday rentals in Casentino

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Top-rated villa rentals in Casentino

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Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 193 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 188 reviews

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Guest favourite

Villa in Siena

4.98 out of 5 average rating, 170 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Guest favourite

Villa in Siena

4.89 out of 5 average rating, 273 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time passes slowly according to ancient traditions. One of the most beautiful views that the Tuscan panorama can offer, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, parking free, WI-FI internet.

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 133 reviews

A paradise in Montepulciano...

Villa Il Cubo is a full centralized air conditioned private house with large private swimming pool placed in the best garden spot for incredible views on the countryside around. Decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY!!!!!!

Superhost

Villa in Rignano sull'Arno

4.95 out of 5 average rating, 131 reviews

Experience the Authentic Charm of Tuscany!

Welcome to Villa La Conigliera, a charming retreat in the heart of the Tuscan countryside. Located next to an old courtyard, this bright and charming farmhouse offers a perfect mix of rustic authenticity and modern comfort, making it the ideal place for a romantic escape or a quiet stay. Same property: Villa La Colonica and Il Fienile, both villas can host 6 people both. It is mandatory to have a car or a motorcycle to move around independently in the surrounding area

Guest favourite

Villa in San Casciano

4.97 out of 5 average rating, 105 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Guest favourite

Villa in Montespertoli

4.94 out of 5 average rating, 164 reviews

Colonica in the Chianti

Beautiful portion of farmhouse immersed in Chianti with beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with large garden and parking spaces. It is 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (hometown of Boccaccio) and Vinci (hometown of Leonardo Da Vinci). the house is halfway between Montespertoli and San Casciano (7km).

Guest favourite

Villa in Monteroni D'arbia

4.95 out of 5 average rating, 114 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance within the "Caggiolo" farm, brought back to light with careful and deep renovation that has kept the typical features of a Tuscan farm intact. Beautiful panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Guest favourite

Villa in Siena

4.95 out of 5 average rating, 136 reviews

The Lemonhouse: A Tuscan dream ~

If you are looking for a calm yet stimulating space to treat yourself while discovering Tuscany, this is the place for you. Formerly home of my family, we recently adibited the spaces of the lemonhouse to welcome guests in a warm yet professional manner. Hopefully you will not miss out on comfort while staying here. Siena 10' - Firenze 50'h - Montalcino 1h - Montepulciano 45' - Grosseto 1h 20'

Guest favourite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 128 reviews

Villa Poggio a Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

Guest favourite

Villa in Bagno a Ripoli

4.97 out of 5 average rating, 118 reviews

Quite old farmhouse on the hills of Florence

Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 25 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more!