Some info has been automatically translated. Show original language

Holiday rentals in Montefollonico

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Montefollonico

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

1 of 1 pages1 / 1
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.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 137 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
A charming terrace features a small round table and two white chairs, offering expansive views of the surrounding hills and distant landscape. A walnut tree stands nearby, enhancing the tranquil outdoor space bathed in natural light from the setting sun.
Apartment in Montepulciano
5.0 out of 5 average rating, 133 reviews

The walnut tree view, Montepulciano

The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

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, 242 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.

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, 328 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, 79 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, 508 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, 114 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.

Top guest favourite
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.
Apartment in Pienza
5.0 out of 5 average rating, 158 reviews

Tuscan country house at Mascagni Farmhouse 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?

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, 92 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.

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.

Guest favourite
A serene infinity pool reflects the clear blue sky, surrounded by olive trees and well-maintained greenery. Lounge chairs are placed around the pool, providing leisure seating with scenic views of the rolling hills beyond.
Farm stay in Monticchiello
5.0 out of 5 average rating, 13 reviews

Lamino, Panoramic apartment, Val d'Orcia Pienza

This charming farmhouse with a breathtaking view of Pienza and the rolling hills of the Val d'Orcia will immerse you in country life thanks to the typical exposed beams, terracotta floors, stone fireplaces and original furnishings recovered by expert hands. The apartment consists of two double bedrooms with bathroom, kitchen and living room with fireplace.

Popular amenities for Montefollonico holiday rentals