Vacation rentals in Castel del Piano

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Top-rated vacation rentals in Castel del Piano

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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

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!

4.93 out of 5 average rating, 288 reviews

Top guest favorite

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

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!

4.92 out of 5 average rating, 620 reviews

Top guest favorite

A wooden dining table is positioned beneath shelves holding decorative items and books. A plant in a vase adds a touch of greenery. A staircase is visible in the background, along with a cabinet displaying more books and decor on nearby shelves.

Apartment in Castel del Piano

Casa Cecilia Farm

Apartment in a house surrounded by greenery, near the village of Castel del Piano. It overlooks the chestnut grove of the property and beyond the view is lost along the valley of the Ente river until you can see the Brunello vineyards and the centuries-old olive trees. The apartment consists of a living room, a kitchen, and a bedroom. Possibility to use the wood-burning oven and barbecue as well as the garage for bicycles and motorcycles ideal for discovering the wonders of Monte Amiata. Tourist tax to be paid on-site

4.99 out of 5 average rating, 288 reviews

Guest favorite

The stone villa is surrounded by lush greenery, showcasing rustic charm with wooden shutters. Sunlight filters through the trees, highlighting the well-maintained lawn and inviting outdoor areas that complement the serene, natural setting.

Villa in Arcidosso

Stone villa with a pool

The stone villa is isolated and surrounded by the greenery of the woods. Here you will find peace, privacy, silence and unspoiled nature. This is the ideal place for a relaxing vacation. The villa was built in the mid-1800s by my great-grandfather. Then over the years it has been restored, improved, always maintaining the classic Tuscan style. We are located between the Val d'Orcia, Monte Amiata, and the sea. We are located 870m above sea level. The villa is about a 15-minute drive from Arcidosso.

5.0 out of 5 average rating, 22 reviews

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

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.

4.94 out of 5 average rating, 145 reviews

Top guest favorite

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

4.92 out of 5 average rating, 331 reviews

Guest favorite

Villa in Poggioferro

Poggio Fra gli Ulivi

Nel cuore della Val d’Orcia, circondato da dolci colline e uliveti a perdita d’occhio, Poggio fra gli Ulivi offre la perfetta combinazione di comfort e relax. Finiture di pregio aggiungono un tocco di autenticità senza tempo a una dimora estremamente accogliente. La piscina e la zona relax godono di una vista mozzafiato. Dal poggio si possono facilmente raggiungere San Quirico, Bagno Vignoni, Pienza, Montalcino e Montepulciano, borghi ricchi di storia e tradizione enogastronomica.

4.83 out of 5 average rating, 12 reviews

Guest favorite

A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.

Cottage in Seggiano

EcoLodge – modern design in a peaceful panoramic location

The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.

4.94 out of 5 average rating, 110 reviews

Top guest favorite

An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.

Farm stay in Seggiano

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

4.99 out of 5 average rating, 290 reviews

Top guest favorite

An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.

Villa in Sarteano

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

4.97 out of 5 average rating, 158 reviews

Guest favorite

A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.

Condo in Castelnuovo dell'Abate

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

4.9 out of 5 average rating, 324 reviews

Top guest favorite

The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.

Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

4.99 out of 5 average rating, 117 reviews