Holiday houses in Montalcino

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Top-rated holiday rentals in Montalcino

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Villa in Castiglion d'orcia

4.96 out of 5 average rating, 107 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 favourite

Home in Prato

4.98 out of 5 average rating, 128 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment, there might still be availability. Turquoise: https://www.airbnb.com/rooms/plus/9430389

Superhost

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.

Guest favourite

Villa in Figline Valdarno

4.98 out of 5 average rating, 44 reviews

Il Castellaccio di Figline

L'alloggio si trova al PRIMO PIANO di una villa immersa nel verde denominata “Il Castellaccio”, che deve il suo nome alla vicinanza con le rovine del vecchio castello appartenuto alla famiglia degli Uberti. La casa gode di una magnifica vista sulla campagna circostante ed è ideale per una vacanza rilassante per famiglie o gruppi di amici, con la possibilità di visitare città d’arte e godere degli splendidi paesaggi del Chianti, nonché delle specialità enogastronomiche della zona.

Guest favourite

Villa in Allerona

5 out of 5 average rating, 29 reviews

Vakantievilla Casale Colline Dolci

Located near the village of Allerona on the border of Tuscany and Umbria, this luxurious villa (casale) is 15 km from Orvieto, 100 km from Rome and 120 km from Firenze. Casale Colline Dolci is perfect for guests who want to enjoy the beauty of the Italian countryside and its excellent cuisine in every comfort and tranquility, but just as well ideal for those who want to soak up the beautiful culture of Italy.

Guest favourite

Apartment in Sasso D'ombrone

4.82 out of 5 average rating, 55 reviews

Holiday house "La Sartina"

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

Guest favourite

Apartment in San Gimignano

4.93 out of 5 average rating, 103 reviews

Apartment "Il Nespolo" - Sunflower Location

The apartment "Il Nespolo", location "Girasole", is located in the historic center of San Gimignano, just 150 meters from Piazza del Duomo, in a cross street of the main street. The property is located in the immediate vicinity of all points of interest and at the same time away from the noise of the busiest street in the country.

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.

Superhost

Farm stay in Pienza

4.8 out of 5 average rating, 165 reviews

Holidays in Piandimaggio in Val d 'Orcia.

Holidays in Piandimaggio The farmhouse "Piandimaggio" Tuscan farmhouse from the early 1900s with 4 new apartments The farmhouse is located in the heart of the Val d'Orcia natural park near Pienza and Bagno Vignoni and with a splendid view of Mount Amiata.

Guest favourite

Farm stay in Greve in Chianti

4.87 out of 5 average rating, 188 reviews

La Capanna delle Bartaline

L'appartamento si trova all'interno della nostra azienda agricola ad 1 Km. da Panzano. E' di nuova ristrutturazione e ben curato nei dettagli, confortevole e luminoso, adatto per ogni tipo di soggiorno. Vista mozzafiato sulle colline toscane.

Superhost

Apartment in Scrofiano

5 out of 5 average rating, 4 reviews

Apartment with patio, A/C

Newly renovated apartment for 4 people. With private patio, garden, located in medieval village. Every bedroom has air condition. Beautiful, quiet place, few steps from forest an d waterfalls.

Guest favourite

Farm stay in Roccatederighi

4.92 out of 5 average rating, 127 reviews

Holiday in antique farm, Belvedere

Fattoria di Peruzzo, Podere Serratina, Appartamento Il Belvedere The cottage in the front faces a terraced lawn from whose baluster a marvellous view can be enjoyed.