Vacation rentals in Montalcino

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, 245 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, 182 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, 130 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.

4.97 out of 5 average rating, 260 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

Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.

4.92 out of 5 average rating, 93 reviews

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.

Apartment in Montalcino

Bruna's House

LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom

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"

The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

4.98 out of 5 average rating, 120 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.

Home in San Quirico d'Orcia

A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.

4.99 out of 5 average rating, 213 reviews

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.

5 out of 5 average rating, 119 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?

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, 294 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.

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"

The farm IL PODERUCCIO has several apartments, including: - A romantic apartment opened in 2019 consisting of a private bathroom and a single room with double bed, single sofa bed and equipped kitchen. Independent entrance, private loggia for outdoor dining, and a magical window overlooking a breathtaking view. Possibility of using the sweet and savory BREAKFAST service, served, at an additional cost of €12 per person per day.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Popular amenities for Montalcino vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Montalcino

5 out of 5 average rating, 8 reviews

A covered terrace is visible, featuring large sliding glass doors that provide a view of the fortress and surrounding greenery. Two bar stools sit beside a stone-topped table, inviting relaxation and enjoyment of the outdoor scenery.

Apartment in Montalcino

gazebo con vetrate scorrevoli

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

5 out of 5 average rating, 19 reviews

A breathtaking view of the sunrise over misty hills is captured, with soft light illuminating the landscape. Underneath, a spacious garden is visible, featuring a few lounge chairs and canopies, while vibrant greenery enhances the serene outdoor space.

Townhouse in Montalcino

Podere Ampella House with a Beautiful View

Villa in San Quirico d'Orcia

A two-story stone farmhouse is set against a clear blue sky, featuring a traditional tiled roof and green shutters. Lush trees and shrubs surround the building, with a gravel pathway leading to the entrance, emphasizing the serene countryside views.

4.98 out of 5 average rating, 51 reviews

Tuscan villa in the heart of the Val d'Orcia

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, 4 reviews

Stunning loft in Montalcino.

4.88 out of 5 average rating, 67 reviews

A fenced outdoor pool is surrounded by lush greenery, with tall trees lining the perimeter. Comfortable lounge chairs are positioned nearby under large umbrellas, offering shaded areas for relaxation. The pool area is designed for enjoyment and tranquility in a naturally scenic setting.

Farm stay in Montalcino

Ginepro Apartment Podere Giardino

5 out of 5 average rating, 6 reviews

A welcoming entryway transitions into an elegantly furnished space featuring a comfortable chair positioned near a plant. Bookshelves adorn the wall, while light enters through a doorway leading to a neatly made bed in a bedroom visible in the background.

Apartment in Montalcino

typical house with a view of Montalcino