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Holiday Homes in Montalcino

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Montalcino

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home in Poggibonsi
4.94 out of 5 average rating, 205 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

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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
5.0 out of 5 average rating, 129 reviews

L'Aquila e L'Ulivo

All'Aquila e l'Ulivo, un antico casale ristrutturato del 1200, troverai non solo tutti i confort necessari per uno splendido soggiorno, ma vivrai anche l'emozione di sentirti libero e immerso nella natura incontaminata della Val D'Orcia. Qui avrai la possibilita' di passeggiare con i due falchi Ayga e Sayen e interagire con le aquile, e perchè non sorseggiare un eccellente aperitivo a bordo piscina. Ti aspettiamo nel nostro mondo, fatto di animali, relax, natura e anche un pizzico di Magia.

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Guest favourite
A bright double bedroom is presented with a spacious bed featuring crisp white linens. Natural light floods the room through an open window, framing a view of the surrounding valley. Wooden beams add character to the ceiling, and bedside tables with lamps are positioned beside the bed.
Holiday home in Montepulciano
4.92 out of 5 average rating, 207 reviews

Stuart Jasmine central, panoramic top location

This abode boasts 1 double and 1 single bedroom, a spacious living room with a fully equipped kitchen, and 1 bathroom with shower. Every window frames a breathtaking view, filling the space with natural light. High-speed Wi-Fi ensures comfort for both work and leisure. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

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Superhost
A private swimming pool is surrounded by lush greenery and a well-maintained yard. The clear blue water reflects the sunny sky above. A ladder is positioned at the pool's edge, while the rustic exterior of a house can be seen in the background.
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.

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Top Guest favourite
An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.
Holiday home in Badia a Passignano
5.0 out of 5 average rating, 123 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

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Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 161 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

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Top Guest favourite
Holiday home in Petrignano
4.98 out of 5 average rating, 167 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.

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Superhost
Holiday home in Reggello
4.88 out of 5 average rating, 226 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

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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
4.96 out of 5 average rating, 137 reviews

In Toscana Camere

**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.

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Top Guest favourite
An expansive window offers a breathtaking view of rolling hills and valleys, extending into the distant horizon. A small table with a laptop is positioned in front, accompanied by a white chair. Soft light fills the inviting space, emphasizing the serene landscape outside.
Holiday home in Rosennano
4.99 out of 5 average rating, 103 reviews

La Loggia. House with pool and stunning view

LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.

FamilyLocationAccuracy

Guest favourite
The image depicts a historic church from the XVI century, characterized by its brick façade and charming architecture. Nestled among greenery, it stands against a serene sky during twilight, highlighting the surrounding hills and countryside.
Holiday home in Chianciano Terme
4.92 out of 5 average rating, 104 reviews

Villa Madonna della Rosa

Villa a few steps from the historic center but facing the countryside and the famous 16th century Madonna della Rosa church, there is a private parking for guests inside the property, the structure is surrounded by a garden and in front of an olive grove. there is a gazebo in the garden surrounded by Tiglio trees, a solarium on the top floor. The villa has all the comforts and large outdoor green spaces.

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Guest favourite
A spacious sleeping area features a decorative bed with light-colored bedding and plush pillows. Soft towels are neatly arranged at the foot of the bed. Natural light filters through a window adorned with dark curtains, highlighting the room's rustic charm.
Holiday home in Pienza
4.92 out of 5 average rating, 115 reviews

Pienzalettings

Rilassati in questo spazio tranquillo nel piccolo borgo. La nostra casa vacanze PienzaLettings è un'esplosione di unicità e bellezza, dotata di un fascino senza tempo. Dotato di ogni comfort, è pronto ad accogliervi e pronto a farvi vivere un'avventura rilassante ed emozionante in un luogo senza tempo. Non sono inclusi 1€ di tassa di soggiorno per persona a notte, esclusi minori di 15 anni

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