Villa vacation rentals in Montepulciano

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Top-rated villa rentals in Montepulciano

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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, 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 favorite

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 102 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

4.97 out of 5 average rating, 159 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 La Poggerina

4.97 out of 5 average rating, 37 reviews

Villa La Poggerina, private pool and amazing view

Living the Tuscan dream. Villa la Poggerina is a beautiful Tuscany Farmhouse villa for rent (300 sq.m inside and 400 sq.m outside) surrounded by hills and vineyards wih a spectacular view. The farm house is located at 300 meters above sea level in the heart of tuscany (Greve in Chianti and Valdarno countryside) where the guests can enjoy a fresh and peaceful environment, very close to the cities of Florence, Siena, Cinque Terre, Arezzo or the tuscan sea. Amazing view and Private pool.

Guest favorite

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!!!!!!

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 Todi

5 out of 5 average rating, 48 reviews

VILLA INCANTO-TODI

Villa Incanto è una nuova residenza esclusiva e di prestigio che ad oggi è limitata al solo piano terra del casale, la restante parte della struttura è ancora chiusa e chi deciderà di soggiornarvi avrà quindi la privacy più totale. Villa Incanto si trova all’interno di una tenuta di 20 ettari che gode di una posizione di mezza collina si gode di un meraviglioso affaccio panoramico di ampio respiro sulle colline umbre.

Guest favorite

Villa in Monteroni D'arbia

4.95 out of 5 average rating, 114 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 Monte Castello di Vibio

4.98 out of 5 average rating, 46 reviews

Totally private Villa 15mt heated pool on 2 acres.

Villa dolce vita is a totally private, elegant stone house situated on a private road immersed in the green Umbrian hills. The pool can be heated for maximum comfort in spring and autumn. The house is made in stone and shows the main characteristics of Umbrian rural architecture. Immersed in a breathtaking green landscape, Villa dolce vita offers an unforgettable vacation of relaxation and tranquility.