Holiday houses in Monterongriffoli

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Top-rated holiday rentals in Monterongriffoli

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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

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and 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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

LocationValueGetting around

4.97 out of 5 average rating, 194 reviews

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.

Condo in Asciano

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!

LocationFamilyAmenities

4.99 out of 5 average rating, 233 reviews

Guest favourite

Home in Asciano

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.

FamilyLocationGetting around

4.96 out of 5 average rating, 138 reviews

Guest favourite

Farm stay in Montalcino

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.

FamilyLocationBackyard

4.98 out of 5 average rating, 44 reviews

Superhost

Home in Monterongriffoli

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.

LocationComfortBiking

4.8 out of 5 average rating, 5 reviews

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

"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.

FamilyValueGetting around

4.98 out of 5 average rating, 49 reviews

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

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

LocationValueBreakfast

4.92 out of 5 average rating, 331 reviews

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.

Condo in Torrenieri

[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.

LocationFamilyBackyard

4.97 out of 5 average rating, 312 reviews

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

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.

LocationValueView

4.97 out of 5 average rating, 69 reviews

Top Guest favourite

Home in San Giovanni d'Asso

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

LocationValueView

5.0 out of 5 average rating, 81 reviews

Top Guest favourite

A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.

Farm stay in San Quirico d'Orcia

Podere Pereti Nuovi – Modern Tuscan Villa

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.

ValueFamilyAmenities

4.98 out of 5 average rating, 116 reviews

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.

Condo in Pienza

Tuscan country house at Mascagni Farmhouse in 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?

FamilyLocationWi-Fi

5.0 out of 5 average rating, 159 reviews