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Holiday rentals in Montefollonico

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Top-rated holiday rentals in Montefollonico

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Villa in Montepulciano
4.97 out of 5 average rating, 125 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

Superhost
Flat in Scrofiano
5.0 out of 5 average rating, 3 reviews

Panoramic View New Apartment with Balcony and A/C

This apartment is part of Anguria Toscana, a collection of charming stays in the medieval village of Scrofiano, in the heart of Tuscany. Spacious and full of natural light, the apartment features beautiful open views over the Tuscan countryside, a private balcony, air conditioning, and a traditional fireplace.The large living spaces and separate fully equipped kitchen make it ideal for longer stays, couples or families looking for comfort and authenticity Free public parking is available nearby.

Top guest favourite
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.
Guest house in Macciano
4.97 out of 5 average rating, 244 reviews

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.

Superhost
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat in Montepulciano
4.98 out of 5 average rating, 162 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 329 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Superhost
A charming terrace features a small table surrounded by comfortable chairs, offering a breathtaking view of the rolling Tuscan hills. Tall cypress trees frame the landscape, and natural light floods the space, creating a peaceful atmosphere for relaxation.
Flat in Montefollonico
4.85 out of 5 average rating, 80 reviews

Charming Tuscan Home with Splendid Terrace

Welcome to Belvedere Toscano, a charming and authentic retreat in the heart of Montefollonico, one of Tuscany's most evocative and timeless villages. Nestled in the historic atmosphere of the city center, the apartment is the perfect base for exploring some of the area’s most iconic destinations, such as Montepulciano, Pienza, San Quirico d’Orcia, and Torrita di Siena. The real gem of the house is its incredible panoramic terrace: an intimate, relaxing, and simply unforgettable space.

Top guest favourite
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
5.0 out of 5 average rating, 509 reviews

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.

Top guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5.0 out of 5 average rating, 115 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Guest favourite
A warm living space showcases exposed wooden beams and light-colored walls. A staircase leads to an upper level, while a cozy seating area features a light gray sofa. A dining table is positioned near windowed doors that offer views of the surrounding countryside.
Apartment in Montefollonico
4.9 out of 5 average rating, 93 reviews

Tuscan Dream Apt with Pool, View & Tennis Court

Discover Il Chicchino, an iconic and authentic retreat housed in an ancient monastery dating back to 1170 in the heart of Montefollonico, between Val d'Orcia and Valdichiana. Here, history, tranquillity and Tuscan charm blend with comfort, an Olympic-size swimming pool, a tennis court and well-kept gardens. An incredible place for couples or friends looking for relaxation, beauty and a truly unforgettable stay immersed in the true soul of Tuscany.

Guest favourite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Flat in Montepulciano
4.91 out of 5 average rating, 304 reviews

I Tramonti di Eramo, central Montepulciano.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

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, 136 reviews

In Tuscany Rooms

**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
Apartment in Montefollonico
5.0 out of 5 average rating, 31 reviews

Toskana Charme: Montefollonico!

Discover picturesque Montefollonico from our unique Airbnb. With breathtaking views of the Tuscan hills, our home is in a prime location. Enjoy the comfort of a large living room, kitchen, bedroom, and study/bedroom. A garden with a barbecue, dining area, and two balconies complete the dream. Montefollonico is the ideal base for exploring the region's beauty. Montepulciano, Pienza, and Montalcino are all within easy reach.

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