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Holiday rentals in Monterongriffoli

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Top-rated holiday rentals in Monterongriffoli

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

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 194 reviews

Casa al Gianni - The Simignano Barn

Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Top guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia
4.92 out of 5 average rating, 621 reviews

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Top guest favourite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Apartment in Asciano
4.99 out of 5 average rating, 233 reviews

Pink like the sunset sky

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 139 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
Farm stay in Montalcino
4.98 out of 5 average rating, 44 reviews

Tuscan Farmhouse ~ Magic Sunsets ~ 360° view

Apt. 'Maria'-Tucked away among the gentle hills of Montalcino and at the heart of the Brunello wine region, an authentic Tuscan farmhouse sits gracefully atop a hill, offering a stunning 360° panorama of the surrounding countryside. Here, amidst ancient vineyards and olive groves, time moves slowly, wrapped in the silence and beauty of the Val d'Orcia. It is the ideal refuge for those in search of tranquility and relaxation, where each sunset paints unforgettable scenes that linger in the heart.

Superhost
Home in Monterongriffoli
4.8 out of 5 average rating, 5 reviews

Truffle N Bed Full Tuscan Stay

Enjoy exclusive access to all three rooms at Truffle N Bed—Bella Vista, Morning Glory, and Intimate Nest. Each offers its own charm, from sweeping countryside views to cozy terrace mornings and romantic hideaways. Perfect for families or groups, this peaceful retreat is surrounded by olive trees, nature, and Tuscan beauty. Relax, reconnect, and experience the magic of slow living in the Val d’Orcia while still being close to all the popular attractions like Montalcino, Montepulciano and Siena.

Top guest favourite
A stone staircase leads to a second-floor entrance, surrounded by lush greenery and flowering plants. The building is partially illuminated, highlighting the texture of the stone. A small terrace with seating is visible at the top of the stairs.
Farm stay in Montalcino
4.98 out of 5 average rating, 49 reviews

"Lunetta" Private Apartment on Larger Property

Le Coppiole is an exciting new addition to our properties at the Ville Ferrano. This "agriturismo" is associated with our olive oil and wine activities. The property is situated in the midst of the most tranquil and breathtaking Tuscan countryside. We offer three homes for rent, either individually or together for a large group. The infinite edge pool is located to take advantage of the stunning views and sunsets. The Lunetta apartment is located on the second floor of the Lunette building.

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 331 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

Top guest favourite
A spacious bedroom features warm brick walls and a wooden beamed ceiling. A large bed with a striped blanket is positioned next to a cozy seating area. A desk and chair setup is visible, along with a Smart TV mounted above, completing the functional space.
Apartment in Torrenieri
4.97 out of 5 average rating, 315 reviews

[9 minutes from Montalcino] Elegant House Mafalda

Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.

Top guest favourite
A warm living area features a stone wall and wooden beams overhead. Comfortable seating includes a gray sofa and two light blue armchairs. A dining table is set with wine and glasses, while modern lighting adds a subtle glow. Natural light enters through a window with a plant view.
Home in Buonconvento
4.97 out of 5 average rating, 70 reviews

Wine House

Enjoy an authentic Tuscan experience in this private apartment within a renovated farmhouse, surrounded by the countryside. Just a few minutes by car from Montalcino and Buonconvento, it’s ideal for those seeking nature, wine and tranquility. Guests have exclusive use of a large fenced garden, outdoor lounge area, BBQ and wood-fired oven. The property is 2 km from Buonconvento (1 km unpaved road); restaurants and shops are in the village, a short drive away. Car recommended.

Top guest favourite
Home in San Giovanni d'Asso
5.0 out of 5 average rating, 81 reviews

Country chic house in a village,private pool,wiFi

La Capanna is a small house hidden at the sight in the very heart of the village of San Giovanni d'Asso in the Community of Montalcino.Private fenced pool (3x6 mt,1mt deep) ,astonishing view from the patio and terrace in front of the house. It can comfortably hold a party of 5 adults plus a child up to 12 . Central heating, fireplace (wood is provided at a little cost)AirCon in the bedrooms, (included in the price from June to mid September) WiFi good for home working

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5.0 out of 5 average rating, 159 reviews

Tuscan rural house in Mascagni Farmhouse Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

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