Villa holiday rentals in Montalcino

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Top-rated villa rentals in Montalcino

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Guest favourite

Villa in Montalcino

5.0 out of 5 average rating, 44 reviews

Breathtaking Views from a Tuscan Villa

We are offering our luxury villa as the setting for your dream Tuscan holidays. The restored tower-house is set within its own olive grove and surrounded by Brunello vineyards. High on the Val D'Orcia side of Montalcino, it enjoys picture perfect views. The village can be reached by a footpath in 15 minutes or by car in 5 mins. The villa benefits from air-conditioning throughout and underfloor heating; bedroom windows also have mosquito nets. The laundry room has a washing machine, iron and ironing board for guests’ use. The villa is perfect for a large family or two to four couples with children. The entire place is available to guests, with the exception of storage rooms in an annex outside the main building. Guests will enjoy exclusive use of the villa and its ground (including swimming pool). For extra safety, the swimming pool area is fenced and can be locked for children. Throughout the stay the guests will be able to contact our professional property managers who will also be able to help with extra activities (to be arranged separately). The villa is set high on the Val D'Orcia side of Montalcino and surrounded by Brunello vineyards. From here, the village is a picturesque 15-minute walk away where exceptional family-owned bistros and boutique shops are just waiting to be discovered. Notwithstanding the history of place, we strived to provide all modern comforts, such as TV with sound bar, a music system, a kitchen radio and a bluetooth speaker. Wifi is provided free of charge throughout the villa and also in the main outdoor spaces - including the pool area. The swimming pool is un-heated, however thanks to its natural, darker colour usually the water warms up more than white or light blue coloured pools. Please note that the swimming pool will be open from 15 May to 15 October - exceptions to be agreed upon based on length of stay / at extra cost.

4–11 Oct

$1,506 SGD per night

Guest favourite

Villa in Castiglion d'orcia

4.95 out of 5 average rating, 77 reviews

Villa Vignalunga

Discover paintings, found art, and original sculptures from room to room in this spacious villa. Old and new worlds collide as chic bathrooms share the space with ancient beamed ceilings. Admire sweeping countryside views from a stone terrace. Villa Vignalunga has been recently, uniquely constructed with traditional materials and preserves all the architectural details of the historic Tuscan farmhouses. Furnished with extreme taste with a mix of still old and modern but always in a rustic original style The villa is surrounded by 46 hectares of picturesque land boasting olive groves, lush vineyards, plentiful orchards, and meadows for grazing horses. Go for a scenic hike or drive to a nearby town for fresh local cuisine.

13–20 Nov

$1,055 SGD per night

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

13–20 Apr

$846 SGD per night

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 181 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

8–15 Feb

$533 SGD per night

Guest favourite

Villa in Siena

4.97 out of 5 average rating, 152 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

13–20 Nov

$244 SGD per night

Guest favourite

Villa in Buonconvento

4.96 out of 5 average rating, 45 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

A beautiful spot in the rustic Tuscan beauty. This untouched landscape of endless rolling hills covered with grain or sunflowers is the absolute protagonist in Valdorcia. Also a rich green valley encompasses the Orcia river, and don’t forget the vineyards for the renowned wines of Brunello or one of the many thermal baths of the region, such as the ones in Bagno Vignoni, where you can relax yourself. It is no wonder that this territory is protected as a World Heritage Site by UNESCO.

11–18 May

$470 SGD per night

Guest favourite

Villa in Montepulciano

4.95 out of 5 average rating, 116 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!!!!!!

2–9 Feb

$547 SGD per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 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. Here time passes slowly according to ancient traditions. 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, original and working fireplace, parking free, WI-FI internet.

24 Feb – 3 Mar

$1,043 SGD per night

Guest favourite

Villa in San Quirico D'orcia

4.98 out of 5 average rating, 52 reviews

I Pereti nuovi-modern Tuscan Villa stunning views

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

3–10 Mar

$487 SGD per night

Guest favourite

Villa in Monticchiello

4.98 out of 5 average rating, 111 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

9–16 Jan

$873 SGD per night

Guest favourite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 110 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.

3–10 May

$749 SGD per night

Guest favourite

Villa in Tignano

4.95 out of 5 average rating, 147 reviews

The best stay in Tuscany Spring

In the Chianti's heart, independent comfortable villa on top of a sunny hill surrounded by an astonish 360° view on the Tuscan Countryside btw Siena and Florence. 2800sqm fenced private garden with pool, wi-fi indoor & outdoor, sat TV, barbecue and wood pizza oven!

18–25 Apr

$679 SGD per night