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Holiday rentals in San Giovanni d'Asso

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Top-rated holiday rentals in San Giovanni d'Asso

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 197 reviews

Casa al Gianni - The Simignano Barn

Converted from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, 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, with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this little slice of paradise!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 141 reviews

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.

Superhost
Holiday home in San Giovanni d'Asso
4.84 out of 5 average rating, 99 reviews

Cottage "Casa Luisa "with private pool

The house is independent and consists of 2 apartments. The house is located about 500 meters from the medieval village of S. Giovanni D'Asso. The apartment is very comfortable and bright and surrounded by a private garden with gazebo, barbecue. The swimming pool is private. In the village you can taste excellent dishes in the "La locanda del castello" restaurant and "Osteria delle Crete". The location allows you to quickly reach the most beautiful places in the Val d'Orcia , Crete Senesi.

Guest favourite
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
4.95 out of 5 average rating, 146 reviews

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.

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
4.92 out of 5 average rating, 332 reviews

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

Top guest favourite
Aerial view of a charming countryside villa surrounded by rolling hills and vineyards. Olive trees are visible lining the roads, which lead to the home nestled within a serene natural landscape. The colors and textures reflect the characteristic beauty of the Tuscan countryside.
Apartment in Asciano
4.98 out of 5 average rating, 324 reviews

Celeste – The color of the summer sky in Tuscany

The apartment is located on the 2nd floor and consists of 2 bedrooms (possibility of making single or double beds on request), a bathroom, a living room, and a kitchen equipped for cooking. (Washing machine available from 9 a.m. to 8 p.m. in the laundry room) Free parking and wifi. Convenient location for visiting Tuscany's tourist centers. We are in the countryside, in the heart of the Crete Senesi, a car is recommended to be independent and visit the magnificent Tuscan countryside

Top guest favourite
Home in San Giovanni d'Asso
5.0 out of 5 average rating, 81 reviews

Country chic house in a village,private pool,wiFi

La Capanna is a small house hidden at the sight in the very heart of the village of San Giovanni d'Asso in the Community of Montalcino.Private fenced pool (3x6 mt,1mt deep) ,astonishing view from the patio and terrace in front of the house. It can comfortably hold a party of 5 adults plus a child up to 12 . Central heating, fireplace (wood is provided at a little cost)AirCon in the bedrooms, (included in the price from June to mid September) WiFi good for home working

Superhost
A spacious living area showcases a staircase leading to the upper level. Natural light enters through large sliding glass doors that open to a scenic outdoor view. A dining table is positioned nearby, complemented by neutral-toned seating arrangements and modern decor elements.
Flat in San Giovanni d'Asso
4.94 out of 5 average rating, 36 reviews

Cozy apartment in the Crete Senesi

Marika's House is a bright and spacious apartment in San Giovanni d'Asso, in the heart of the Crete Senesi. Located in a strategic position, it allows for easy exploration of Montalcino, Pienza, Montepulciano, and the Val d'Orcia, and is also close to the thermal spas. Surrounded by Tuscany's rich food and wine traditions, amidst prestigious wine regions like Brunello and Nobile, it offers a tranquil and comfortable stay for an unforgettable experience.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5.0 out of 5 average rating, 161 reviews

Tuscan rural house in Mascagni Farmhouse 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?

Top guest favourite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento
4.89 out of 5 average rating, 100 reviews

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

Top guest favourite
A spacious bedroom features soft pink walls and warm lighting. A large bed with neutral bedding is set against a backdrop of draped curtains. A wooden vanity table, a mirror, and a decorative rug add to the room's charm, creating a cozy and inviting atmosphere.
Apartment in San Giovanni d'Asso
4.97 out of 5 average rating, 61 reviews

Apartment in the historic center of San Giovanni d'Asso

The ancient 13th-century building that houses the apartment "La Casa del Castello" overlooks the square of the historic center of San Giovanni d'Asso, an extremely quiet, peaceful and charming area. Closed to traffic. Kitchen, relaxation lounge, bathroom, one bedroom and study with sofa bed, are spread over 70 sqm. Convenient location to stay in a relaxing atmosphere and reach various, renowned tourist resorts or small villages to discover.

Guest favourite
Home in San Giovanni d'Asso
4.88 out of 5 average rating, 65 reviews

Ca' Montalcino

Ca' Montalcino is a delightful apartment located within the walls of the ancient castle of San Giovanni d'Asso, one of the beautiful hamlets of Montalcino, in the heart of Val d'Orcia. From San Giovanni d'Asso you can reach many of the most impressive destinations in the area: from Pienza to Bagno Vignoni, to Rapolano Terme, to Montepulciano and Montalcino itself. Siena, Arezzo, Perugia and the sea are about an hour's drive away.

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