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Holiday Homes in Montalcino

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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
4.95 out of 5 average rating, 201 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.

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, 123 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.

Top 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, 205 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.

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, 119 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

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, 159 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.

Top Guest favourite
A serene salt-water pool reflects the bright blue sky, surrounded by stone walls and green landscaping. Two lounge chairs offer spots for relaxation, while an umbrella stands nearby, enhancing the outdoor space. The tranquil setting invites peaceful moments by the water.
Holiday home in Orvieto
4.99 out of 5 average rating, 120 reviews

Casa Isla, near Orvieto, amazing views + pool

Located between the villages Viceno and Benano with incredible views of Orvieto and surrounded by olive trees. Casa Isla is a refurbished 70sqm 2 bedroom cottage next to the main house, completely self-contained with its own private garden and BBQ area. There is a double bedroom and a second with twin-beds, both with air-con. The lounge/kitchen comes with fridge, gas hob, oven, and dishwasher, a sofa bed, and a smart TV for movie nights. Relax in our salt-water/mineral pool.

Top Guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home in San Gimignano
4.98 out of 5 average rating, 158 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Top Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home in loc. Simignano
4.92 out of 5 average rating, 236 reviews

Casa al Gianni - Quercia

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Top Guest favourite
Holiday home in Petrignano
4.98 out of 5 average rating, 156 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.

Guest favourite
Holiday home in Porto
4.95 out of 5 average rating, 140 reviews

La Dimora del Lago - Lake views Tuscany and Umbria

Straddling the Tuscan-Umbrian border, sitting on a millennial Etruscan archeological heritage and surrounded by Montepulciano vineyards and Chianina cattle country, overlooking tiny Lake Chiusi — this authentically restored 500-year-old watchtower sits semi-detached in a quiet rural hamlet, halfway between Florence and Rome. Near Orvieto, Cortona and Lake Trasimeno. Under 2 hours by motorway or train from either city. Fast WiFi and Netflix included. .

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
4.97 out of 5 average rating, 133 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.

Top 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
4.93 out of 5 average rating, 110 reviews

Pienzalettings

Relax in this peaceful place in the small village. Our PienzaLettings vacation home is an explosion of uniqueness and beauty, with a timeless charm. Equipped with every comfort, it is ready to welcome you and ready to make you experience a relaxing and exciting adventure in a timeless place. Not included: €1 tourist tax per person per night, excluding children under 15 years of age

Popular amenities for Montalcino holiday homes

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Montalcino
  6. Holiday home rentals