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Villa vacation rentals in Cortona

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Top-rated villa rentals in Cortona

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Villa in San venanzo

4.88 out of 5 average rating, 108 reviews

country house

Il chiericciolo è una casa di campagna sulle fantastiche colline umbre vicino a Todi e Perugia. La casa ha una vista a 360 gradi su vigne, noci e boschi. La casa è molto grande e accogliente con un bel camino, inoltre è attrezzata con una cucina per divertirsi a cucinare i prodotti tipici locali. La casa è stata ristrutturata lasciando tutti i muri in pietra, le travi di legno castagno a vista e il cotto originale. Mentre gli impianti di riscaldamento e i bagni sono completamente nuovi. Passare una notte al chiericciolo è un'esperienza unica.

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.

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

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.

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

Villa in San Venanzo

4.9 out of 5 average rating, 111 reviews

Casa Boschetto, villa with private pool

The rural house was built with ancient stone sourced locally in Umbria and offers a breath taking view overlooking the surrounding valley. The house encompasses a spacious living-room with two antique fire places, two kitchens, a recreation room, five bedrooms & four bathrooms. Outside there is a large swimming pool, dining area, a play house for children, multiple car-parking options and a 2 car fully enclosed garage. There are also a BBQ and a wood fire oven if you wish to cook outside.

Villa in Cortona

5 out of 5 average rating, 43 reviews

Casa Pietro Berrettini in Cortona

Casa Pietro Berrettini is located in the oldest and most characteristic neighborhood of the city of Cortona. Independent, immersed in an environment full of history and culture, ideal for spending pleasant and extremely relaxing stays. Bright living room area with panoramic terrace. Large private garden, very well maintained, with a view over the entire valley. Three bedrooms, each with private bathroom and hot tub/shower, well finished independent apartment ground floor of the villa.

Villa in Siena

4.89 out of 5 average rating, 274 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. 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, fireplace, parking free, WI-FI internet. In winter and early spring there is an extra charge of 40€ a day for heating.

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!!!!!!

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.

Villa in Sarteano

4.96 out of 5 average rating, 101 reviews

Casale in Val D’Orcia

Tuscan farmhouse of the 1800s with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-acre park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We have been in the beautiful Val d 'Orcia, a UNESCO World Heritage Site since 2004.

Villa in Monticchiello

4.99 out of 5 average rating, 139 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

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Popular amenities for Cortona villa rentals

Free parking on premises

Air conditioning

Private villa rentals

Villa in Castiglion Fiorentino

5 out of 5 average rating, 6 reviews

Podere Ortaglia Di Sopra

Villa in San Casciano dei Bagni

5 out of 5 average rating, 42 reviews

Luxury Retreat in the Tuscan Hills

Villa in Montepulciano

5 out of 5 average rating, 17 reviews

Villa Nobile - Private Jacuzzi

Villa in Gaiole In Chianti

4.89 out of 5 average rating, 19 reviews

Sestuccin

Villa in Civitella in Val di Chiana

4.9 out of 5 average rating, 71 reviews

Villa with Pool Casa la Quiete

Villa in Gaiole in Chianti

5 out of 5 average rating, 16 reviews

Montemarcoli

Villa in San Casciano dei Bagni

4.98 out of 5 average rating, 59 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

Villa in Arezzo

4.99 out of 5 average rating, 81 reviews

Tuscany View - Villa Arianna with indoor SPA

Luxury villa rentals

Villa in Pienza

4.91 out of 5 average rating, 32 reviews

Villa I Cipressini Tuscany Private luxury pool spa

Villa in Asciano

4.94 out of 5 average rating, 80 reviews

Casa Bianca gorgeous Tuscan home, Crete Senesi

Villa in Torrita di Siena

4.88 out of 5 average rating, 69 reviews

Villa Poggio Becchi. Infinity pool and valley view

Villa in Passignano sul Trasimeno

4.9 out of 5 average rating, 30 reviews

Villa with Panoramic Pool on Lake Trasimeno

Villa in Lisciano Niccone

5 out of 5 average rating, 8 reviews

Secret villa with tree house

Villa in Pergine Valdarno

4.95 out of 5 average rating, 86 reviews

La Vignaccia (Farmhouse) - villa w/private pool

Villa in Monte Vibiano Vecchio

5 out of 5 average rating, 5 reviews

Luxury Villa, Stunning Views in the heart of Italy

Villa in Asciano

4.95 out of 5 average rating, 75 reviews

Podere on the Crete Senesi

Villa rentals with a pool

Villa in Buonconvento

4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

Villa in La Cima

4.93 out of 5 average rating, 30 reviews

Idyllic stone villa with pool & Trasimeno panorama

Villa in Seggiano

5 out of 5 average rating, 7 reviews

Case Bianchi

Villa in Collazzone

4.95 out of 5 average rating, 44 reviews

VILLA ROSETO-TODI

Villa in Lucignano

4.94 out of 5 average rating, 17 reviews

Sasso Canaldo: Elegant Tuscan farmhouse

Villa in Loro Ciuffenna

4.98 out of 5 average rating, 41 reviews

The Lazy Oak

Villa in Castiglione del lago

5 out of 5 average rating, 5 reviews

Country Villa with private pool in Umbria/Tuscany

Villa in Paciano

4.98 out of 5 average rating, 40 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

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