Holiday houses in Montalcino

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Top-rated holiday rentals in Montalcino

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Guest favourite

Home in San Casciano In Val di Pesa

4.84 out of 5 average rating, 92 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

Step under archways into a home where the original wood ceilings and tiled floors showcase Tuscan style. Enjoy delicious meals on the terrace with sweeping views of Tuscany, winters curled up in front of a huge fire place or relaxing on warm summer days by the pool. Savour the best of Tuscan food and wine with cooking classes with a Michelin chef, master classes in wine and visits to local artisan cheese and wine makers. Listed by Condé Nast as one of the most beautiful villas in Italy.

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Villa in Petrignano

4.98 out of 5 average rating, 51 reviews

Restored Farmhouse & Cottage with AC, Pool & WIFI

Villa La Quercia is a private 2 acre property consisting of a beautifully restored farmhouse and cottage- both exclusively for you during your stay. The property is surrounded by farmland and forest providing complete privacy and tranquility, yet the nearest village is only 3kms away. The property comfortably sleeps up to 12 people and has a large salt water filtered swimming pool. Fabulous restaurants, wineries and stunning Tuscan & Umbrian villages are but a short drive. Welcome.

Top Guest favourite

Loft in Scandicci

4.98 out of 5 average rating, 109 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

Guest favourite

Apartment in Sasso D'ombrone

4.81 out of 5 average rating, 59 reviews

"La Sartina" Vacation Home

Beautiful newly renovated house (2023) with a beautiful view of the Ombrone Valley, where you can admire a beautiful sunrise and appreciate the wonderful Tuscan Maremma. Excellent finishes, 4 beds, air conditioning, very central to the typical Tuscan village of Sasso D'Ombrone. 100 meters from the Bar/Market/Emporio, the post office and the bus stop. 1500m from Albus Alpacas (Alpaca Experience). Serious and helpful owner.

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Holiday home in Ortignano Raggiolo

5 out of 5 average rating, 16 reviews

Casa Paolina, typical Tuscan structure

Holiday home in Tuscan style, rustic and cozy, finely restored in accordance with the local tradition. Equipped with every comfort, it will give joy and relaxation to young and old with its large garden, pool and hot tub. Our guests can stay in complete privacy in our structure immersed in nature, in a small village of medieval origin, entirely pedestrian, forged by time and by past generations.

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Home in Castiglione della Pescaia

4.86 out of 5 average rating, 7 reviews

Vacation home in Castiglione

A corner of heaven and tranquility a stone's throw from the sea. A renovated apartment equipped with every comfort with a large garden available to spend summer evenings and enjoy the view of the Diaccia Botrona and the sea. In the hilly area, 2 km from the center of the village, to experience the sea and the village but with serenity.

Guest favourite

Villa in Loro Ciuffenna

4.91 out of 5 average rating, 23 reviews

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.