
Vacation rentals in Roccastrada
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Top-rated vacation rentals in Roccastrada
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Casa al Gianni - The Simignano Barn
Converted from an old 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
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"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 meters where there is 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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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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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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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.
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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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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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Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.
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Villa Il Diaccio with view of the Tuscan Maremma
Stone villa with special architectural finishes nestled in a chestnut forest. A large garden, partly paved with stone, accompanies the property from which you can admire a wonderful view of the Tuscan Maremma. Surrounded by nature, you can see the sea with the Gulf of Follonica, the island of Elba and Corsica on one side, and the island of Giglio on the other. You can take long walks in nature or reach seaside resorts or cities of art.
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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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L'Olivo: Apartment for 2 - Window on the Maremma
L'Alba, a mid-19th century stone farmhouse, finely restored, overlooks a spectacular panorama from which you can admire the Maremma coast, resting on a hill of Mediterranean scrub, almost dominating nature with strong colors and superfine air. The property is divided into only 3 apartments for maximum tranquility. Guests can enjoy a pond-style pool with a whirlpool, set in a fairy-tale lighting frame...
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Tuscany jem: The Chianti Farmer's House
This wonderful newly renovated apartment retains the charm of the Chianti farmhouses and the comforts of a modern apartment. The house is located within the complex of the Fattoria di Petroio, a Chianti Classico winery. You can enjoy the beauty and tranquility of the Chianti hills, while immersing yourself in the dynamic life of a company dedicated to the production of quality wines.
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Popular amenities for Roccastrada vacation rentals
Other great vacation rentals in Roccastrada

La Capanna: country house with magnificent view
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Luxury Penthouse Overlooking Piazza del Campo
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Tuscan Barn Apartment for 6 with panoramic pool
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XIII Century Tower with Private Panoramic Pool
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Podere la Pompa
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Linda's Holiday Home
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Fontino
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Casa Giovy - Relax with a view of the Tuscan hills
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Destinations to explore
- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Del Chianti
- Le Cannelle
- Spiaggia di Capo Bianco
- Mount Amiata
- Cascate del Mulino
- Antinori nel Chianti Classico
- Avignonesi Winery Fattoria Le Capezzine
- Siena Cathedral
- CavallinoMatto
- Vulci
- Val di Chiana
- Quercetano
- Palazzo Pubblico
- Saturnia Thermal Park
- Valdichiana Outlet Village





