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Vacation rentals in Sassofortino

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Top-rated vacation rentals in Sassofortino

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Top guest favorite
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 agritourism property 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 warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

Top guest favorite
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 an enviable 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 good glass of wine, cheers. Have a good trip!

Guest favorite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia
4.95 out of 5 average rating, 146 reviews

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.

Guest favorite
Cottage in Monticiano
4.95 out of 5 average rating, 41 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

Guest favorite
Home in Massa Marittima
5.0 out of 5 average rating, 76 reviews

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.

Guest favorite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia
4.94 out of 5 average rating, 203 reviews

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 107 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Top guest favorite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.98 out of 5 average rating, 129 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Guest favorite
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.

Guest favorite
Dome in Volterra
4.95 out of 5 average rating, 185 reviews

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Top guest favorite
Farm stay in Campiglia D'orcia
4.95 out of 5 average rating, 577 reviews

Poggio Bicchieri Holiday Farm - Poesia Apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large, well-equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Top guest favorite
A spacious living area is fitted with comfortable seating arrangements, including two sofas and a wooden coffee table. Natural light enters through a window covered with light curtains, highlighting the rustic ceiling beams and the textured walls. A decorative rug adds a warm touch to the terracotta floor.
Home in Roccatederighi
4.96 out of 5 average rating, 50 reviews

A HOUSE WITH A PANORAMIC VIEW OF MEDIAEVAL TOWN

The house is located at the heart of the small mediaeval town of Roccatederighi, at 537 m above sea level, with a panoramic, uninterrupted view overlooking the Maremma plain all the way to the sea. It has three floors, accommodates 6 persons, has a large kitchen and a spacious living room with top quality finishes.

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