
Holiday rentals in Montefollonico
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Top-rated holiday rentals in Montefollonico
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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.
4.97 out of 5 average rating, 126 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
4.98 out of 5 average rating, 165 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
4.93 out of 5 average rating, 334 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
4.95 out of 5 average rating, 146 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.
5.0 out of 5 average rating, 36 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.
4.85 out of 5 average rating, 80 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.
5.0 out of 5 average rating, 116 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.
4.91 out of 5 average rating, 97 reviews
In Tuscany Rooms
**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.
4.96 out of 5 average rating, 137 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.
5.0 out of 5 average rating, 33 reviews
Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.
4.95 out of 5 average rating, 579 reviews
Podere Lamino, Val d'Orcia, Pienza
This charming farm with a breathtaking view of Pienza and the rolling hills of the Val d'Orcia consists of two apartments equipped with all the comforts that will make you immerse in the country life thanks to the typical exposed beams, the terracotta floors, the fireplaces in stone and the original furnishings.
4.99 out of 5 average rating, 67 reviewsPopular amenities for Montefollonico holiday rentals
Other great holiday rentals in Montefollonico

Luxury Penthouse with Incredible View & A/C 300mq
4.98 out of 5 average rating, 99 reviews
Villa with garden. The Cardinal's Garden.
4.97 out of 5 average rating, 97 reviews
Charming Tuscan Home · Montepulciano & Val d'Orcia
5.0 out of 5 average rating, 5 reviews
Beautiful apartment+terraces+A/C in 13th century town
4.62 out of 5 average rating, 69 reviews
Tuscan Village Apartment, Montefollonico, Pienza
5.0 out of 5 average rating, 5 reviews
At Gabri's house, hospitality and simplicity
5.0 out of 5 average rating, 16 reviews
Villa Banditello, view over Montepulciano valley
4.84 out of 5 average rating, 32 reviews
[15 min from Montepulciano] Villa Chiara
4.91 out of 5 average rating, 23 reviewsDestinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Eremo Di Camaldoli
- La Scarzuola
- Antinori nel Chianti Classico
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Mount Subasio
- Basilica Di San Miniato A Monte
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Abbey of Sant'Antimo
- Casa Barthel





