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.

4.97 out of 5 average rating, 242 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.

4.96 out of 5 average rating, 168 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, 126 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.

A spacious living area showcases a modern sectional sofa accented by decorative throw pillows. A glass coffee table sits in front, and a large TV is mounted on the wall opposite. Soft lighting highlights the charming ceiling details and a marble fireplace adds an elegant touch.

5 out of 5 average rating, 9 reviews

New Palazzo in City Center: 4 King Bedrms 6 Bath

Experience this newly restored historic home in the center of Montalcino, built for one of the most influential families in Montalcino. Imagine having dinner in the 500 year old wine cellar or relaxing in bed as you look up at beautiful frescos on the ceiling. This four bedroom home complete with a large living room, dining room/kitchen, and wine cellar dining room is updated with the latest amenities, appliances, high-speed internet, and comfortable lush bedding. Opening July 4, 2024

5 out of 5 average rating, 461 reviews

An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.

Loft in Montepulciano

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

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, 117 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.

4.96 out of 5 average rating, 354 reviews

A scenic view captures a rustic stone house set amid rolling hills and olive trees. The expansive landscape features golden fields and lush green foliage, with a winding path leading to the home. The sky is clear, enhancing the serene countryside atmosphere.

Condo in Asciano

Romantic Yellow apartment in Crete Senesi

Apartment consisting of a comfortable double bedroom (it is possible to make 2 single beds on request), an equipped kitchen, a living room, and a bathroom. TV, BBQ, (if needed, we have a washing machine available from 9 a.m. to 8 p.m., which is in our laundry room). A car is recommended as we are in the countryside, so you can be self-sufficient and visit the magnificent Tuscan countryside as well. Free parking and wifi. I look forward to showing you the real Tuscany!

4.99 out of 5 average rating, 114 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, 210 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.

Superhost

An outdoor seating area is presented beneath a spacious gazebo, featuring a wooden table and chairs. A hanging chair offers a comfortable spot for relaxation. A grill stands ready for cooking, with expansive views of the surrounding vineyards and rolling hills visible in the background.

4.89 out of 5 average rating, 9 reviews

NEW Panoramic loft with garden in Montalcino

Nestled among vineyards and centuries-old olive trees in Montalcino, Tuscany. For those seeking modern comfort and rustic charm, our loft is the perfect choice! Carefully renovated, it offers a cozy and refreshing space with a spacious living room for conviviality and relaxation, and a romantic loft with a double bed. Outside, a panoramic garden with a furnished gazebo and private parking. Ideal for couples or families who love nature, wine, and fine cuisine.

Condo in Castelnuovo dell’Abate

A welcoming living area showcases wooden beams across the ceiling and a charming fireplace, adding warmth to the space. A television is mounted on the wall, while a stylish white cabinet and comfortable armchairs are arranged around the central hearth, inviting relaxation.

4.9 out of 5 average rating, 307 reviews

Il Borghetto: Alice's House, charm and relaxation

Alice's House is located in the central area for the visit of Valdorcia and Montalcino with its Brunello wineries. All renovated and very bright, it can sleep 2 to 4 people. Entirely covered by Wifi, it has two double bedrooms, each with a private bathroom, a kitchen equipped with a relaxing living room with LED TV, armchairs, wood-burning fireplace for the cold evenings in winter. Heated with clean energy and restored with eco-friendly materials.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

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Convenient locations with everyday essentials

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Luxurious estates for the ultimate escape

Popular amenities for Montalcino vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Montalcino

A shared fenced pool is surrounded by lush greenery and stone pathways. Sun loungers and an umbrella provide shaded seating, while tall trees frame the backdrop against a clear blue sky. The pool is designed for seasonal use and is accessible during designated hours.

Farm stay in Montalcino

4.81 out of 5 average rating, 36 reviews

Glicine Apartment Podere Giardino

4.9 out of 5 average rating, 360 reviews

A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.

Apartment in Montalcino

Panoramic Country Suite Montalcino

5 out of 5 average rating, 114 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

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

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.

4.88 out of 5 average rating, 100 reviews

agriturismo il poderuccio "sweet apartment"

4.98 out of 5 average rating, 182 reviews

The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.

Home in Monticchiello

"La Lambarda" tower Suite

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.