Holiday houses 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, 456 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, 191 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, 262 reviews

Montepulciano Centro 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, 127 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, 274 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 .

Apartment in Monticchiello

4.97 out of 5 average rating, 152 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

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Other great holiday rentals in Montefollonico

Farm stay in San Quirico d'Orcia

4.99 out of 5 average rating, 83 reviews

Podere Pereti Nuovi-modern Tuscan Villa

MichaelRating, 5 stars1 day ago

Fabulous. Spectacular. Breath taking. Phenomenal. Not sure what other superlatives I can use. Incredible stay at an incredible property with an incredible host in an incredible location. We will be back. Eight of us staying in this beautiful home. San Quirico d’Orcia is an absolute perfect place to stay in Tuscany if you are planning to go to the hill towns. Can’t recommend enough.

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 evocative, despite not being among the most "known", and located in a strategic position to spend a weekend in Val d 'Orcia!

4.91 out of 5 average rating, 22 reviews

Cottage in Montepulciano

Angalia Guesthouse

LauraRating, 5 stars1 week 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.

4.99 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!