Holiday houses in Castiglione 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!

La Sorpresa Studio Apartment

Studio apartment in the heart of Pitigliano, a short walk from the Synagogue and the Etruscan Vie Cave. The apartment offers a beautiful view of the Meleta valley. It is carefully furnished with antique and valuable furniture and objects. It offers a smart working station. The house is located in the center of Pitigliano, just a few meters from the Synagogue and the “Etruscan hollow streets”. It offers an amazing view of the Meleta Valley. The apartment is furnished with care and with fine antiques.

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Da nonna Ornella - nest in Val d'Orcia

Vista spettacolare e relax assicurato in questo romantico monolocale nel cuore della Val d’Orcia, provincia di Siena, immerso nella splendida Toscana. Ideale per coppie. Dispone di zona living, cucina accessoriata, bagno, riscaldamento, resede, parcheggio privato e un grande e panoramico giardino con lettini e amaca. Vicino a mete iconiche: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d’Orcia, Radicofani, Castiglione d’Orcia e Monte Amiata. Indimenticabile.

Fontarcella, H&R- mediterranean home with jacuzzi

Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

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.

Apartment in a detached villa - Val d'Orcia

In villetta indipendente accogliente appartamento in stile toscano recentemente e finemente ristrutturato e situato in una terra ricca di storia. A pochi km da città d'arte e sulla via Francigena, l'appartamento può essere base per percorsi naturalistici o enogastronomici. Da una bella terrazza sul panorama potrete godere i vostri pasti, ammirare il tramonto ed osservare la maestosa e magnifica Rocca medioevale .Dal 22/03/18 tassa di di soggiorno comunale2 € a persona. Vedi note aggiuntive

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Borgo71 - In the Heart of the Val d'Orcia

Immerse yourself in the authentic charm of the Val d'Orcia from this ideal house, nestled in a stunning Tuscan region famous for its gentle hills, medieval towns, and distinctive hues. Recently renovated in 2025, it offers modern technologies and comforts while preserving the characteristic stone features of the old village houses. This is the perfect base for exploring Montalcino, Pienza, Bagno Vignoni, San Quirico, Siena, and numerous other amazing destinations in the vicinity.

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

La casa nel Borgo - Superior Tuscany Apartment

La Casa Nel Borgo is located in the small medieval village of Monticchiello, inside the historic center, between the ancient walls, immersed in the classic and enchanting landscapes of Tuscany. Newly renovated, it perfectly blends its historical soul with modern decor, giving the environment personality and charm. The terrace with a view is equipped. NOTE: *Only one room will be available for 2 people, unless explicitly requested.*

La porta di Neno

Apartment in Val d'Orcia of 80 square meters, overlooking the beautiful valley located on the first floor of a small condominium in the center of the village of Castiglione d'Orcia. Bright and recently renovated apartment, very comfortable, suitable for families, couples or small groups of friends. It is equipped with everything you need to stay. Wi-Fi is available. Public parking 30 meters away. There is no air conditioning.