Villa vacation rentals in Arezzo

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Top-rated villa rentals in Arezzo

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Guest favorite

Villa in San Leolino

5 out of 5 average rating, 105 reviews

Poggio del Fattore-Villa with pool,hilltop,Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Guest favorite

Villa in Lisciano Niccone

4.85 out of 5 average rating, 41 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Guest favorite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 191 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 favorite

Villa in Impruneta

4.99 out of 5 average rating, 95 reviews

Welcome Home - 8 miles to Florence & heated pool

A truly indulgent getaway⁠, where every pristine detail is taken care of. The concierge service provided means you can rely on a dedicated team to anticipate your every need. Explore Florence Old Town at 20 minutes away by car. Raising a toast with a glass of Chianti on your private heated salted water pool - this 17th Century - Villa is the very definition of effortless Tuscan living. A unique experience and stay, ideal for those seeking their own private space on the Florentine hills

Guest favorite

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 106 reviews

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

Guest favorite

Villa in Montepulciano

4.96 out of 5 average rating, 166 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Guest favorite

Villa in Montepulciano

4.96 out of 5 average rating, 134 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!!!!!!

Guest favorite

Villa in Cortona

5 out of 5 average rating, 69 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Guest favorite

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 favorite

Villa in Barullo-Centoia

4.91 out of 5 average rating, 43 reviews

Bellora: A Perfect Villa in Cortona, Tuscany

Discover the epitome of Tuscan luxury at our exquisite villa, boasting an idyllic location near Cortona. A mere 15-20 minute drive to Cortona and 25 minutes to Montepulciano, it offers unparalleled convenience for exploring Tuscany. Nestled within a private gated estate, this opulent haven showcases 3 bedrooms, 2 pristine bathrooms, and a generously-sized swimming pool exclusively reserved for your indulgence. Youtube: "Villa Bellora Cortona Drone fly by"

Guest favorite

Villa in Monteroni d'Arbia

4.95 out of 5 average rating, 117 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" estate, returned to light with careful and deep renovation that has kept the typical guidelines of a Tuscan farm intact. Beautiful panoramic view of Siena. Located in the Villas of Corsano, only 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 favorite

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.