
Holiday houses in Montepulciano
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Top-rated holiday rentals in Montepulciano
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La Toscana in terrazza, Montepulciano centro
Benvenuti a Montepulciano, il gioiello nascosto della Toscana, dove il fascino storico si fonde armoniosamente con la bellezza naturale. Il nostro Airbnb nel cuore del centro storico incarna l'eleganza e l'autenticità di questa regione. Immersi nel suggestivo labirinto di stradine lastricate di pietra, sarete accolti dal suono rassicurante dei campanili che annunciano il passare del tempo, mentre il profumo invitante del pane appena sfornato si mescola con le note aromatiche dei nostri vigneti.

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.

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

Montepulciano Centro Storico
Grazioso appartamento di 60 mq situato nel corso principale del paese. Si trova al secondo ed ultimo piano di un palazzo storico. L'ingresso è situato sul corso principale della cittadina mentre le finestre si affacciano verso l'esterno delle mura offrendo un vista mozzafiato. L'appartamento è composto da: ingresso, soggiorno con divano letto matrimoniale, camera da letto, cucina, bagno con finestra a tetto. E' dotato di forno a microonde, forno grande, lavastoviglie, lavatrice e wi-fi.

"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.
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla 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, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

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.

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.

I Tramonti di Eramo , Montepulciano centro.
Benvenuti a Montepulciano, il gioiello delle colline toscane! Il nostro appartamento nel cuore del centro storico offre una vista mozzafiato sulla campagna circostante, regalando un'esperienza autentica e indimenticabile. Potrete uscire di casa e assaporare l'atmosfera storica di Montepulciano. A pochi passi avrete la straordinaria Piazza Grande, ristoranti di ottima qualità e servizi di ogni genere. La Toscana vi aspetta per vivere emozioni uniche.

Agriturismo Poggio Bicchieri ap. Poesia
Il nostro agriturismo è una finestra sulla val d'orcia, composto da 2 appartamenti con cucina, camera e bagno. Grande giardino attrezzato. Immerso nel silenzio, vicino a Pienza, Montalcino, Bagno Vignoni e le terme naturali di Bagno San Filippo. Per raggiungerci è molto semplice, l'ultimo km di strada è sterrata ma percorribile da tutti.

"La Lambarda" tower Suite
In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.
Popular amenities for Montepulciano holiday rentals
Other great holiday rentals in Montepulciano

Casa Tòrta - comfort room

Agriturismo Via della Stella | Casa le Rose

a.d. 1237

Dimora dell'Erbe - Rooftop Apartment

Magnificent 2 BR with Terrace and Air Conditioning

Hortus Conclusus House

Wine Loft tra le vigne

Mery's House: elegant apartment
Quick stats about holiday rentals in Montepulciano
Total rentals
310 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
17K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
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- Lake Trasimeno
- Lake Bolsena
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cala Di Forno
- Tenuta Le Velette
- Terme Dei Papi
- Marina di Grosseto beach
- Basilica of St Francis
- Castiglion del Bosco Winery
- Cantina Colle Ciocco
- Golf Club Toscana
- Santa Maria della Scala
- Pubblico Palace
- Mount Subasio
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Casa Del Cioccolato Perugina
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Azienda Agricola Montefioralle Winery