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Holiday houses in Roccastrada

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Top-rated holiday rentals in Roccastrada

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

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 292 reviews

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

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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, 625 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!

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Top Guest favourite
A private swimming pool is visible amidst lush greenery, framed by vibrant flowers in shades of pink and purple. The serene landscape stretches into the distance, revealing rolling hills under a soft evening sky.
Loft in Roccastrada
5.0 out of 5 average rating, 67 reviews

"Casa Chiassarello" with pool

Casa Chiassarello is located in a quiet and panoramic location, a short walk from the center of Roccastrada. The house, entirely made of stone, is built from an old oil mill. The accommodation is an open space of about 80 square metres with a very spacious kitchen, a bathroom, a sleeping area with TV and fireplace; it overlooks a spacious veranda that can be used as a dining area and relaxation area. Guests have access to the garden and swimming pool, both for exclusive use, there are no other guests on the property.

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Guest favourite
Villa in Ribolla
5.0 out of 5 average rating, 6 reviews

Podere Raspollino | Maremma 10 people

Podere Raspollino is a Maremma farmhouse. It consists of two floors. On the ground floor, there are two bedrooms and two bathrooms with an independent entrance! In the loggia overlooking the pool, you can find a barbecue and a fully equipped kitchen (without an oven)! Dining table and armchairs! On the second floor, there are three bedrooms and three bathrooms, a living room and a full kitchen! The farmhouse is located between Ribolla and Montemassi! About 55 minutes from Siena The nearest airport is Pisa

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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, 332 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

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Top Guest favourite
Apartment in Roccatederighi
4.98 out of 5 average rating, 42 reviews

Domus Olea BnB

The Domus Olea apartment is part of a Tuscan stone farmhouse that overlooks the Maremma from a prime location. It takes its name from the wonderful restored oil mill, set into the marble base that has been embedded in the floor for over a century. It will be an experience of relaxation and greenery, of sunsets over the sea on the horizon, amidst timeless architecture and a minimalist approach to space. A hot tub to pamper yourself, time for a nice glass of wine, cheers. Have a good trip!

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Guest favourite
Condo in Roccastrada
4.92 out of 5 average rating, 39 reviews

Casa Mary, independent entrance, private garden

Exclusive fenced garden, open space, double room, large bathroom. Park your car for free, visit the village, and enjoy evocative food and wine experiences (excursions, tastings, natural, historical, and architectural sites). Take a walk to discover natural and historical wonders with stunning views. LACASASALUTARE® Mary, restyling in Color and Shabby style by ARCHFMS®️-ARCHITETTURA SALUTARE®️, Emotional Design, Furnishing Objects by Spolverati Francesca Maria, Holistic Bio-Architect.

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Top Guest favourite
Cottage in Monticiano
5.0 out of 5 average rating, 40 reviews

Typical Tuscan Cottage with swimming pool and park

The Country Cottage is located in the heart of authentic Tuscany, in an unspoiled area, with a unique biodiversity. Located just a 5-minute drive from the famous Abbey of San Galgano and the Hermitage of Montesiepi, where the prestigious "Sword in the Stone" is kept. The entire property is rented: the typical Tuscan country house, the swimming pool, the garden and the fenced park. A perfect location to relax with maximum privacy, without the stress and wear and tear of modern life

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Guest favourite
Two comfortable loungers are positioned on a stone terrace, offering an expansive view of rolling green hills and the distant village of Roccatederighi. Sunlight streams across the scenery, while a small table holds a bottle and glass, inviting relaxation amidst nature.
Villa in Roccatederighi
4.94 out of 5 average rating, 18 reviews

Villa Casale "Il Diaccio" with views of the Maremma

Villa Casale with large garden partly in grass and partly in stone slabs. Immersed in nature and lying on a comfortable sunbed, the town of Roccatederighi divides the horizon, on one side the view of the sea with the Gulf of Follonica and beyond the Island of Elba and Corsica, on the other the Maremma plain and the island of Giglio. You can walk in nature, admire the local fauna, go by bike, relax by taking a bath in the mini pool or reach the cities of art.

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Top Guest favourite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento
4.89 out of 5 average rating, 100 reviews

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

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Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 21 reviews

Luxury penthouse with a view of Piazza del Campo

There are many houses in Siena. But very few can say they are here. Overlooking the city's most iconic square, this penthouse offers a rare experience: waking up with the golden light that caresses the Palazzo Pubblico and falling asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you are immersed in history, among restaurants, wines and timeless atmospheres.

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Guest favourite
Home in Monteroni d'Arbia
4.97 out of 5 average rating, 64 reviews

Golden View - Dream Farmhouse in Tuscany

A peaceful corner among beautiful cypress trees, where silence and tranquility reign. Relax in the hydromassage waterfall in the garden, light the fireplace on cooler evenings, or enjoy a barbecue. The master bedroom pampers you with a hot tub and private sauna. The outdoor tub will be usable from May 1 to November 1 of each year, then it can be used on request but the internal water will not be able to exceed 25 degrees.

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