Vacation rentals in Montefollonico

4.96 out of 5 average rating, 165 reviews

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.

4.95 out of 5 average rating, 219 reviews

Villa in Montepulciano

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

5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

4.92 out of 5 average rating, 127 reviews

Condo in Montepulciano

"Dimora Valinda" Montepulciano Piazza Grande +A/C

🏠 Ideal location: within walking distance of stores, restaurants and attractions in the historic center. ❄️ Air conditioning for maximum comfort during hot days. 🛁 Washing machine for extended stays or simply for traveling light. 🌅 Private terrace for relaxing moments outdoors. 🍴 Full kitchen with dishwasher, perfect for those who love to cook even on vacation. 🌐 Ultra-fast 150 Mb/s Wi-Fi, ideal for smart working ☕ Well-stocked coffee station for a perfect start to the day.

4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2025 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Guesthouse in Montefollonico

4.97 out of 5 average rating, 103 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

5 out of 5 average rating, 457 reviews

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.

4.94 out of 5 average rating, 196 reviews

I Tramonti di Eramo, Montepulciano city center.

Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historical center offers a breathtaking view of the surrounding countryside, giving an authentic and unforgettable experience. You can leave the house and taste the historic atmosphere of Montepulciano. Within walking distance you will have the extraordinary Piazza Grande, high quality restaurants and services of all kinds. Tuscany awaits you to experience unique emotions.

4.99 out of 5 average rating, 263 reviews

Montepulciano Downtown Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. Apartment consists of: entrance hall, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

4.91 out of 5 average rating, 128 reviews

Tuscany on the terrace, downtown Montepulciano

Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region. Immersed in the charming labyrinth of cobblestone streets, you will be greeted by the reassuring sound of bell towers announcing the passage of time, while the inviting scent of freshly baked bread mixes with the aromatic notes of our vineyards.

4.99 out of 5 average rating, 275 reviews

Apartment in Sinalunga

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

5 out of 5 average rating, 111 reviews

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?

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Popular amenities for Montefollonico vacation rentals

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Free parking on premises

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Other great vacation rentals in Montefollonico

Apartment in Montefollonico

5 out of 5 average rating, 3 reviews

Lovely 'La Segreta' – Borgo di Sotto Tuscany

GretaRating, 5 stars1 month ago

My boyfriend and I stayed in Niccolò's apartment for two nights. Our experience was more than positive: the host was immediately very helpful and kind both in providing us with all the information and curiosities about the area, and in answering any questions or concerns. The village is very charming, despite not being among the most "known", and located in a strategic position to spend a weekend in Val d'Orcia!

Condo in Sinalunga

5 out of 5 average rating, 4 reviews

The Secret

JonathanRating, 5 stars2 days ago

We had a wonderful time in this charming accommodation in Tuscany! Everything was just like in the pictures – clean, tastefully furnished and with a lot of love for detail. The host and his wife were incredibly friendly and helpful, which made our stay even more enjoyable. We felt completely comfortable and can wholeheartedly recommend this place!

4.91 out of 5 average rating, 22 reviews

Cottage in Montepulciano

Angalia Guesthouse

LauraRating, 5 stars2 weeks ago

The accommodation was very clean, well-designed, comfortable and situated in a beautiful and authentic tuscan location. The hosts are lovely people who respond to everything within minutes and come up with interesting activity recommendations. We absolutely recommend this house to everyone who loves a peaceful place to stay at in the heart of Italy.

4.98 out of 5 average rating, 54 reviews

Farm stay in Montalcino

Agriturismo MONSOLE - Sleep in a dream ...

ScottRating, 5 stars1 week ago

Our stay at Agriturismo Monsole was fantastic! The house was very clean and well maintained. The views were amazing, and it was an extremely peaceful location. Carmela was a great host, very welcoming, and was very helpful in organizing a cooking class as well as providing recommendations of activities to do.

4.99 out of 5 average rating, 68 reviews

Condo in Montepulciano

a.d. 1237

HeatherRating, 5 stars1 week ago

What an incredible stay!! 10/10. We traveled all over Tuscany for 2 weeks and this stay ranks right up there at the top. From the communication and ease of getting to the apartment to the beautiful old history of the building and town. Just wow! Book it:) We loved the town and her people🫶🏼 The apartment was comfortable in every way. Grazie mille, Heather & Beth

Apartment in Montefollonico

4.87 out of 5 average rating, 38 reviews

Villa Andreucci

GytisRating, 5 stars1 month ago

Really great stay, and really nice apartment with wonderful hosts! The apartment has a huge garden and two terraces in a very quirky and nice building surrounded by nature. It's also nicely finished with interesting furniture, fireplaces - you can sense the history and that this was a living house not some cheap Ikea made Airbnb. The beds were really comfy. It's also very well stocked with tea, coffee, oil, and we even had sweet snacks and juice left for us for breakfast! Eva and Valerio were really really friendly and tried their best to accommodate us and checked-in constantly if everything was ok. There was one issue which could have waited til the morning but Valerio came and fixed it in the middle of the night, much appreciated. And Montefollonico is really tranquil and peaceful small town, we also saw the Vin Santo celebration which gave us a sneak peak at local life. We really enjoyed our stay here ... near the nature, very chick decor with great hosts. Highly recommended!

Farm stay in San Quirico d'Orcia

4.98 out of 5 average rating, 44 reviews

Wine Loft in the vineyards

HilaryRating, 5 stars2 weeks ago

The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.