
House holiday rentals in Castiglione d'Orcia
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Top-rated house rentals in Castiglione d'Orcia
Guests agree: These houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!
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Apartment in a detached villa - Val d'Orcia
In a detached villa, a cozy Tuscan-style apartment, recently and tastefully renovated, located in an area rich in history. Located just a few kilometers from cities of art and on the Via Francigena, the apartment can serve as a base for nature trails or food and wine tours. From a lovely terrace overlooking the panorama, you can enjoy your meals, admire the sunset, and gaze at the majestic and magnificent medieval fortress. .As of March 22, 2018, a municipal tourist tax of €2 per person applies. See additional notes.
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Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in beautiful Tuscany. Ideal for couples. It has a living area, an equipped kitchen, a bathroom, heating, a courtyard, private parking, and a large, panoramic garden with sun loungers and a hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia, and Monte Amiata. Unforgettable.
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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.
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House Rigomagno Siena
Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.
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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.
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TERRAZZA PARADISO- House + roof terrace + parking
Our house is located in the heart of the historic town of Orvieto, at just 5 minutes from the Duomo. A large living area with a fully equipped kitchen is on first floor, on the second floor there are two bedrooms, a bathroom and a small balcony. A huge flowered terrace on Orvieto rooftops will make your stay a memorable one! The terrace is fully furnished and lit: the place where relax and sunbathe during the day or enjoy intimacy at night! Private parking is available at no extra cost.
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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.
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Jenny's Barn
The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.
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The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
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Conca d'Oro villa with private pool, sleeps 4
Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi
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At the Sassone Holiday Home, Val d'Orcia, Tuscany
Treat yourself to relaxing days in contact with nature! Apartment in villa, large garden with hammocks and large volcanic rocks. Direct access to the woods, with a pond and waterfalls, from which a series of paths and hiking trails lead to the free spas of Bagni San Filippo and the summit of Mount Amiata. DISCOUNTS FOR MEDIUM TO LONG PERIODS!
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Popular amenities for Castiglione d'Orcia house rentals
House rentals with a pool

Casa Lucy
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Podere Scorno country house with swimming pool
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Infinity pool in Chianti 1
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Private Chianti Cottage, Garden & Vineyard Views
LocationFamilyHot tub

Vineyards Paradise
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Explore Chianti from a Charming Stone House
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Borgo Ripostena – No. 8 Casa Vecchia
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Country House in the Crete Senesi
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Weekly house rentals

La casa nel Borgo - Superior Tuscany Apartment
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Casa d'Orcia
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Lovely home to dream
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Borgo71 - In the Heart of the Val d'Orcia
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The Bandita dei Bovi
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Raffaella's House in Chianti
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Country chic house in a village,private pool,wiFi
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"La Casa di Maria Luce"® with panoramic terrace
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Private house rentals

Hidden gem in Tuscany
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Maria's home in Awesome Tuscan Unesco location
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Casa San Ripa: Relax Oasis with Private Pool
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Dimora del Poggio: Garden View Suite
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Spacious Luxury Stay in Pienza | 3BR 3BA
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Domus Antiqua
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Tosco Suite "Solis"
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The little house in the banditelle
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Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Cala Violina
- Feniglia
- Del Chianti
- Le Cannelle
- Centro Storico Orvieto
- Cascate del Mulino
- Mount Amiata
- Terme Dei Papi
- Villa Lante
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Antinori nel Chianti Classico
- Vulci
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Terme San Filippo
- Valdichiana Outlet Village
- Riserva Naturale Diaccia Botrona
- Saturnia Thermal Park
- Abbey of Sant'Antimo





