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Holiday houses in Castiglioncello di Trinoro

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Top-rated holiday rentals in Castiglioncello di Trinoro

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Top Guest favourite
Villa in Chianciano Terme

Charming Tuscan Villa in Val d'Orcia with a view

Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

4.97 out of 5 average rating, 130 reviews
Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.97 out of 5 average rating, 251 reviews
Top Guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

4.98 out of 5 average rating, 165 reviews
Guest favourite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suites & Views

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

4.98 out of 5 average rating, 187 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

4.92 out of 5 average rating, 337 reviews
Top Guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
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.

4.98 out of 5 average rating, 160 reviews
Top Guest favourite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Holiday home in Monticchiello

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

4.96 out of 5 average rating, 137 reviews
Guest favourite
The image depicts a serene swimming pool surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and the distant Monte Amiata. The clear water reflects the sky, offering a tranquil atmosphere for relaxation and enjoyment.
Farm stay in Montepulciano

Unique view 3 bdr villa with pool & A/C in Pienza

Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.

4.95 out of 5 average rating, 104 reviews
Top Guest favourite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza

Spedaletto Castle, Val d'Orcia, Pienza

The Castello di Spedaletto farmhouse is located in the building that once housed the granary of the ancient medieval castle and has been recently renovated in perfect balance between modernity and tradition: stone, bricks, exposed beams blend with the characteristic crystal and wrought iron staircase. The farmhouse consists of 5 double bedrooms with bathrooms and 2 apartments. Come, See, Live...

4.97 out of 5 average rating, 185 reviews
Top Guest favourite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

4.96 out of 5 average rating, 170 reviews
Top Guest favourite
Farm stay in Campiglia D'orcia

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 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.

4.95 out of 5 average rating, 579 reviews

Popular amenities for Castiglioncello di Trinoro holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Castiglioncello di Trinoro

Top Guest favourite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Holiday home in Chianciano Terme

The Eagle and the Olive Tree

5.0 out of 5 average rating, 129 reviews
Top Guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

4.99 out of 5 average rating, 233 reviews
Top Guest favourite
A spacious room features a double bed with an orange bedspread, complemented by two wooden nightstands. Natural light floods in through a large window with orange curtains, while a wooden beam ceiling adds character. Vintage decor elements are showcased on the walls.
Farm stay in Chiusi

Breeder's Room - Triple room breakfast included

5.0 out of 5 average rating, 108 reviews
Guest favourite
A spacious pool area surrounded by a wooden fence features lounge chairs and shade umbrellas. The inviting water reflects the clear sky, while a well-maintained garden and a rustic stone villa are visible in the background, creating a serene outdoor setting.
Villa in Sarteano

Villa with private pool, air conditioning, Wi-fi

4.92 out of 5 average rating, 12 reviews
Guest favourite
A welcoming living area features a large fireplace with a warm fire flickering, surrounded by light-colored sofas. A wooden table is centered among the seating, adorned with magazines and a small vase of flowers. Natural light filters in through the windows, highlighting the room's cozy atmosphere.
Apartment in Chianciano Terme

Ronda apartment in Chiarentana, Val d'Orcia

4.95 out of 5 average rating, 22 reviews
Top Guest favourite
A spacious living area is defined by a vaulted ceiling with exposed wooden beams. A green sectional sofa is positioned around a circular table, offering a comfortable seating arrangement. A TV console and a vintage chest contribute to the inviting decor, while natural light enters from a nearby window.
Home in Sarteano

The Court of the Podestà

4.96 out of 5 average rating, 26 reviews
Top Guest favourite
A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.
Holiday home in Monticchiello

Elegant farmhouse overlooking Pienza

5.0 out of 5 average rating, 37 reviews
Guest favourite
An indoor pool is surrounded by rustic stone walls and a vaulted brick ceiling. Soft lighting enhances the tranquil ambiance. A shallow section of the pool is visible, along with steps leading to another area. Cozy cushions are placed nearby, inviting relaxation.
Apartment in Monteleone d'Orvieto

Elegant historic Palazzo, views of Tuscan valley

4.97 out of 5 average rating, 86 reviews