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Vacation rentals in Montefollonico

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montefollonico

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

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

Wine Experience Villa in Montepulciano

🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

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Top guest favorite
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.
Apartment in Montepulciano
4.98 out of 5 average rating, 163 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

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Top guest favorite
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, 332 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

ValueFamilyHeating

Top guest favorite
A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.
Vacation home in Monticchiello
5.0 out of 5 average rating, 36 reviews

Elegant farmhouse overlooking Pienza

Podere Fonte Bernardi is an authentic Tuscan country house. Surrounded by the nature of the Val d'Orcia, an ideal place to relax. Located a few km from the most beautiful places in Tuscany such as Pienza, the medieval village of Monticchiello, the thermal site of Bagno Vignoni and the homeland of Montepulciano wine. Perfect for taking long walks and discovering local wines and food. You will be able to enjoy the most beautiful sunset over Pienza in the silence of the most authentic nature.

LocationFamilyNearby

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.
Apartment in Montefollonico
4.85 out of 5 average rating, 80 reviews

Charming Tuscan Home with Splendid Terrace

Benvenuti al Belvedere Toscano, un rifugio charming e autentico nel cuore di Montefollonico, uno dei borghi più suggestivi e senza tempo della Toscana. Immerso nell’atmosfera storica del centro, l’appartamento è la base perfetta per esplorare alcune delle destinazioni più iconiche della zona, come Montepulciano, Pienza, San Quirico d’Orcia e Torrita di Siena. Il vero gioiello della casa è la sua incredible terrazza panoramica: uno spazio intimo, rilassante e semplicemente indimenticabile.

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Guest favorite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano
4.96 out of 5 average rating, 167 reviews

A paradise in Montepulciano...

Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. IN JULY AND AUGUST WE LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY. Exceptions are possible only if don't create unrentable gaps between one guest and the next.

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Top guest favorite
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.

LocationFamilyWifi

Guest favorite
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.
Apartment in Montepulciano
4.91 out of 5 average rating, 304 reviews

I Tramonti di Eramo, Montepulciano centro.

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.

LocationValueLong stay

Top guest favorite
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.
Vacation home in Monticchiello
4.96 out of 5 average rating, 137 reviews

In Toscana Camere

**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.

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Top guest favorite
Condo 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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Guest favorite
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.
Condo in Montefollonico
4.91 out of 5 average rating, 95 reviews

Tuscan Dream Apt with Pool, View & Tennis Court

Scopri Il Chicchino, un rifugio iconico e autentico ricavato in un antico monastero del 1170 nel cuore di Montefollonico, tra Val d’Orcia e Valdichiana. Qui storia, quiete e fascino toscano si fondono con comfort, piscina olimpionica, campo da tennis e giardini curati. Un luogo incredible per coppie o amici in cerca di relax, bellezza e un soggiorno davvero indimenticabile immerso nell’anima più vera della Toscana.

ValueLocationSleep quality

Guest favorite
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, Appartamento panoramico,Val d'Orcia Pienza

Questo affascinante podere con una vista mozzafiato su Pienza e le dolci colline della Val d’Orcia vi farà immergere nella vita in campagna grazie alle tipiche travi a vista, i pavimenti in cotto, i camini in pietra e gli arredamenti originali recuperati da mani esperte. L'appartamento è composto da due camere matrimoniali con bagno, cucina e soggiorno con caminetto.

LocationFamilyHospitality

Popular amenities for Montefollonico vacation rentals