Holiday rentals in Rocca d'Orcia

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Top-rated holiday rentals in Rocca d'Orcia

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

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to 'Casa al Gianni', our farmhouse 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 peaceful haven will stay in your heart. We look forward to welcoming you!

4.93 out of 5 average rating, 294 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.

Guest house 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

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

Guest favourite

A rustic stone building features a sloped roof and round windows, surrounded by lush greenery. A stone pathway leads to the entrance, where a vine-covered pergola provides shade. Two chairs are placed outside, inviting relaxation in a serene countryside setting.

Farm stay in Castiglione d'Orcia

Agriturismo Il Granaio della Fonte

If you want to spend your vacation in a farm stay in Val d 'Orcia, a few steps from the cities most rich in history, art and tradition in all of Tuscany such as Pienza, Montalcino and Montepulciano, Granaio della Fonte farmhouse is your ideal destination. A Tuscan-style apartment, with a comfortable and spacious double bed, antique furniture, satellite TV and bathroom equipped with all the comforts, will be waiting for you upon your arrival in this wonderful corner of Tuscany.

4.79 out of 5 average rating, 171 reviews

Top guest favourite

A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.

Home in Castiglione d'Orcia

Apartment in a detached villa - Val d'Orcia

A cosy apartment in a detached villa, in a Tuscan style, recently and tastefully renovated and located in an area rich in history. Just a few kilometres from cities of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a lovely terrace with a view, you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 22/03/18, the municipal tourist tax is €2 per person. See additional notes.

4.96 out of 5 average rating, 180 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

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

4.99 out of 5 average rating, 233 reviews

Top guest favourite

A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.

Flat in Castiglione d'Orcia

Mimosa Apartment - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

4.99 out of 5 average rating, 112 reviews

Top guest favourite

A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.

Farm stay in San Quirico d'Orcia

Podere Pereti Nuovi – Modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

4.98 out of 5 average rating, 116 reviews

Guest favourite

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.

Apartment in Castelnuovo dell'Abate

La Casetta di Brunello, very panoramic with terrace

WE'RE WORKING FOR YOU. ... 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 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

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

Guest favourite

A panoramic view of a rustic farmhouse is captured, surrounded by expansive green hills and fields under a bright blue sky. The structure features a traditional tiled roof and is set within a serene countryside landscape, offering a tranquil escape.

Flat in Castiglione d'Orcia

"il poderuccio" two-room farmhouse

The IL PODERUCCIO farmhouse has several apartments, for a total of 11 beds, including: a two-room apartment on the ground floor (sleeps 2) complete with double bedroom, private bathroom with shower and living room with double sofa bed, wood-burning fireplace and fully equipped kitchen. A truly comfortable environment, ideal for couples.

4.93 out of 5 average rating, 121 reviews