Vacation rentals in Montalcino

5 out of 5 average rating, 265 reviews

An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.

Condo in Noce

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

A spacious sleeping area features a large bed adorned with a white coverlet and numerous decorative pillows. Soft lighting is provided by two bedside lamps, creating a calm ambiance. A black and white artwork hangs above the bed, contrasting with the warm, neutral wall color.

4.96 out of 5 average rating, 243 reviews

Montalcino - Casa Gelsomino - garden and relaxation

Immerse yourself in the charm of Montalcino by staying in this enchanting stone vacation home with a private garden, ideal for relaxing moments. Right in the historic center, it offers an authentic and welcoming atmosphere, perfect for exploring the wonders of Tuscany. Take advantage of the central location to visit renowned wineries and enjoy delicious Tuscan cuisine. Discover the wonders of Val d'Orcia, a UNESCO heritage site, and let yourself be captivated by ancient local culture and tradition.

4.97 out of 5 average rating, 177 reviews

A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.

Guesthouse in Macciano

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.

A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.

5 out of 5 average rating, 128 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Home in Castiglione d'Orcia

A spacious living area features a gray sofa adorned with patterned cushions. A rustic wooden table and bookshelves filled with books are visible in the background, illustrating an inviting open layout that connects the living space to the dining area.

4.94 out of 5 average rating, 142 reviews

Apartment in a detached villa - Val d'Orcia

In a detached villa, a cozy Tuscan-style apartment recently and tastefully renovated and located in a land rich in history. A few kilometers from the city of art and on the Via Francigena, the apartment can be a base for nature or food and wine tours. From a beautiful terrace overlooking the panorama you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval fortress From 03/22/18, municipal tourist tax: €1 per person from 12 years old

4.99 out of 5 average rating, 118 reviews

A spacious terrace is showcased with two comfortable armchairs positioned around a glass table. Potted red flowers adorn the railing, overlooking a panoramic view of the rolling hills of the Tuscan countryside under a partly cloudy sky.

Condo in Montalcino

"Landscape Notes" Suite

The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

5 out of 5 average rating, 117 reviews

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.

Condo in Pienza

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?

The image presents a view of a serene outdoor space showcasing a swimming pool surrounded by lush greenery and rolling hills. A large tree provides shade, while flowering plants add color to the scene. The landscape features golden fields stretching into the distance.

4.96 out of 5 average rating, 73 reviews

Focolare for 4 people with swimming pool in Montalcino

Apartment furnished in a rustic style but comfortable and cozy for your vacation in Montalcino and Val D'Orcia. The comfortable kitchen-living room allows you to work remotely, study or devote yourself to your projects. Parking, Wi-Fi, equipped kitchen, air conditioning, heating and private veranda. Infinity pool overlooking the vineyards, shared with other guests of the property. The property is sorry, but pets are not allowed during guests' stay.

An open-concept kitchen and dining area are featured, showcasing modern cabinetry and a dining table with four chairs. Exposed wooden beams contrast with light-colored walls, while an archway adds architectural interest. Natural light fills the space, creating a welcoming environment.

5 out of 5 average rating, 71 reviews

Otello Guest House

L'Otello Guest House vi ospiterà all'interno del centro storico di Montalcino. La casa di Nonno Oti e Nonna Giuli, si presenta con un tradizionale soffitto travi a vista e rifiniture moderne. L'appartamento completamente ristrutturato a Maggio 2021, comprende ingresso al piano terra, luminoso salotto open space con ampio divano e cucina a vista ,camera da letto con armadio spazioso e bagno. A disposizione degli ospiti anche il garage ad uso privato.

Superhost

The bedroom features a spacious bed with light bedding. Natural light floods in through the windows, illuminating the wooden beams and antique furniture, including a tall wooden wardrobe and a small table with a chair. A mirror adds subtle charm to the room.

4.96 out of 5 average rating, 140 reviews

House of the Jujube

Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.

Superhost

A spacious bedroom features a double bed dressed in white linens, with a cozy armchair in the corner. Natural light enters through a window, illuminating the stone wall beside wooden beams above. A wooden table displays snacks and additional seating is available.

Condo in Castelnuovo dell’Abate

4.91 out of 5 average rating, 292 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

4.98 out of 5 average rating, 58 reviews

The image displays a charming Tuscan farmhouse with a stone facade and terracotta roof. An expansive green lawn surrounds the building, adorned with various shrubs and plants. The blue sky is dotted with wispy clouds, creating a serene backdrop to this traditional countryside setting.

Farm stay in Montalcino

Agriturismo MONSOLE - Sleep in a dream ...

Finding your place in the world is the result of the efforts and dreams of a lifetime. Today such a place exists, it is found halfway between Siena and Montalcino and is called Farfalle. Take the dirt road that from the small town of Torrenieri winds through the gentle hills of Val d'Orcia. After a few kilometres, halfway between the loose earth of the fields and the endless sky, you will find an ancient Tuscan villa.

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Popular amenities for Montalcino vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Montalcino

Farm stay in San Giovanni d'Asso

A spacious bed is adorned with a textured white bedspread. Neatly rolled towels are arranged on the bed, accompanied by fresh sunflowers, adding a touch of nature. A wooden nightstand is positioned nearby, accentuated by soft lighting from a lamp.

4.94 out of 5 average rating, 120 reviews

Flat, Agriturismo "Biofattoria l'Upupa"

A well-lit living area displays a comfortable sofa and a stylish armchair, complemented by a wooden coffee table. A smart TV is mounted on the wall, with artful decorations and plants enhancing the space. Three windows provide ample natural light, illuminating the warm wooden ceiling.

Condo in Montalcino

4.69 out of 5 average rating, 58 reviews

Fulvia's home

A spacious open-plan living area is displayed, featuring a modern kitchen with sleek cabinetry and an island. The dining table is set for meals, and a comfortable sofa is positioned in the background. Natural light fills the room, highlighting the wooden beams overhead.

4.92 out of 5 average rating, 92 reviews

Bruna's House

Apartment in Castiglione d'Orcia

The image showcases a sprawling rural landscape viewed from above, featuring a rustic stone building with a terracotta roof. Surrounding areas include lush green fields, trees, and hills in the distance, under a bright blue sky accented by soft, fluffy clouds.

4.89 out of 5 average rating, 105 reviews

agriturismo il poderuccio "sweet apartment"

5 out of 5 average rating, 6 reviews

The exterior of the villa showcases a rustic stone façade, accented by large arched windows and a warm earthy color palette. A well-maintained lawn surrounds the building, complemented by mature olive trees, creating a serene setting against a softly colored sky.

Villa in Montisi

Villa – Pool, Garden, and Tuscan Relaxation

4.97 out of 5 average rating, 255 reviews

A spacious bedroom features warm brick walls and a wooden beamed ceiling. A large bed with a striped blanket is positioned next to a cozy seating area. A desk and chair setup is visible, along with a Smart TV mounted above, completing the functional space.

Condo in Torrenieri

[9 minutes from Montalcino] Elegant House Mafalda

A dining area features a wooden table surrounded by elegant chairs. Large arched windows provide expansive views of the landscape, with rolling hills and distant towns visible. Soft light is diffused through round hanging fixtures, complementing the warm, earthy tones of the walls.

5 out of 5 average rating, 3 reviews

Stunning loft in Montalcino.

Two large arched windows are framed in dark materials, revealing flowing light curtains. The textured stone wall reflects a rustic charm, accompanied by two large planters with greenery placed at the base. A dark pathway leads to the entrance, enhancing the quiet ambiance.