Holiday rentals in Montefollonico

5 out of 5 average rating, 252 reviews

Apartment in Noce

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

4.96 out of 5 average rating, 165 reviews

Guest house 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

Apartment in Montepulciano

4.92 out of 5 average rating, 127 reviews

"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, 106 reviews

Villa in Montepulciano

Wine Experience Villa in Montepulciano

Villa Talosa è una residenza immersa tra i vigneti di "Fattoria della Talosa",Azienda vitivinicola di Montepulciano ove produciamo il Vino Nobile di Montepulciano d.o.c.g . Un luogo per godere di relax con una fantastica vista da ogni finestra della Villa. Distiamo 1.5 km dal centro storico,dove sarà possibile visitare la ns Cantina Storica risalente al 1500 A.D. e collocata sotto piazza Grande . Nota: Riscaldamento ed l’Aria condizionata sono dei costi aggiuntivi, in base al consumo.

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.

4.97 out of 5 average rating, 290 reviews

Apartment in Asciano

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

4.99 out of 5 average rating, 263 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. The apartment consists of: entrance, 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.

4.99 out of 5 average rating, 123 reviews

Guest house in Perugia

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

4.93 out of 5 average rating, 175 reviews

Stuart Jasmine central, panoramic top location

This abode boasts one double bedroom, a living room, fully equipped kitchen, one bathroom, and a charming studio room. Every window is adorned with a breathtaking view of the valley, enveloping the space in natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast Here, you can unwind and relax, study and learn, discover and explore, or create and dream.

Apartment in Castelnuovo dell’Abate

4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

4.82 out of 5 average rating, 104 reviews

Il Segreto di Agnaresi, 30 meters from Caffè Poliziano

Welcome to the beating heart of Montepulciano, where your stay becomes an unforgettable experience. Our newly renovated apartment, designed to accommodate two people, is located in the center of town, just 200 meters from Montepulciano's majestic Piazza Grande, one of the most beautiful squares in Italy, and only 30 meters from the famous Caffè Poliziano, Montepulciano's most historic bar and the third most beautiful bar in Italy.

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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 stars4 days 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.

Flat 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!

Flat in Castiglioncello del Trinoro

5 out of 5 average rating, 315 reviews

Stunning Tuscan apartment in 14 Century Palazzo

SharonRating, 5 stars5 days ago

A truly magical and unique stay in a castle apartment. After 24 days exploring the beauty of Italy, our arrival at Simone's third floor apartment in the village was breathtaking. This truly magnificent setting, nestled within a castle, immediately enveloped us in a serene and peaceful atmosphere. The apartment itself is not only beautifully appointed and meticulously cared for, but also boasts spectacular views across the mountain range that invited us to sit for hours, simply unwinding and soaking in the tranquility. While we ventured down the mountain a few times, we found ourselves drawn to the gentle rhythm of morning and evening walks, always culminating in a visit to the piazza to once again marvel at the stunning views Simone, our host, is simply the most considerate and attentive host I have encountered in 15 years of travel. His dedication ensured our stay was nothing short of exceptional. Grazie mille, Simone, for sharing this incredible piece of paradise with us. We depart

4.92 out of 5 average rating, 36 reviews

Farm stay in Cortona

Poggio Martino | Childfriendly Agriturismo

HenrikRating, 5 stars2 weeks ago

The accommodation and especially the garden looks even more beautiful in reality than in the pictures! The location is really beautiful, it is absolutely quiet and you have a breathtaking view of the Tuscan landscape. Perfect for relaxing and enjoying. The hostess was also super nice, helpful and warm! We will definitely come back:-)

Farm stay in Castiglion Fiorentino

5 out of 5 average rating, 8 reviews

Podere Il Belvedere Farmhouse - La Stalla

BrianRating, 5 stars1 month ago

Max’s place is beautiful like a dream. The accommodation is tastefully furnished with Tuscan charm. The interior is equipped with high quality cooking utensils and tablewares in the kitchen, comfortable bed, and sparkling clean bathroom. We enjoyed marveling at the beautiful wooden beam ceiling and terracotta tile floor. The exterior is elegant, well maintained, and exudes a pride in the care-taking of the property. Max and his wife Pamela were genuinely kind and helpful, and we enjoyed every interaction with them. It felt like talking with family. The location is convenient to explore central Tuscany. We made many day trips from Podere Il Belvedere su Cortona. Every time coming back to Max’s place felt like coming home!

5 out of 5 average rating, 54 reviews

Home in Pienza

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi

AaronRating, 5 stars4 days ago

One of the nicest places I’ve stayed. Like a luxury well decorated boutique hotel. But in Tuscany! We were 3 couples, each had their own room and bathroom.

4.97 out of 5 average rating, 73 reviews

Villa in Monticchiello

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars3 weeks ago

Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.