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Search results; Over 1,000 homes in Montepulciano

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Top guest favourite
Nature lodge in Montepulciano
Bedroom w/Swimming Pool in Tuscany - Montepulciano
1 bedroom, 1 bed, 1 private bathroom
13–18 Oct, Business host
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4.93 out of 5 average rating, 56 reviews
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Flat in Montepulciano
A view from the gate, Montepulciano.
Individual host
15–20 Nov
4.97 out of 5 average rating, 326 reviews
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Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
Individual host
15–20 Sept
4.98 out of 5 average rating, 48 reviews
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Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 53 reviews
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Villa in Montepulciano
Wine Experience Villa in Montepulciano
Business host
16–21 Oct
4.97 out of 5 average rating, 125 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 113 reviews
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Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
Individual host
6–11 Oct
5.0 out of 5 average rating, 96 reviews
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Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
Individual host
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 reviews
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Flat in Montepulciano
The source
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 214 reviews
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Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
Business host
11–16 Nov
4.99 out of 5 average rating, 112 reviews
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Villa in Chianciano Terme
Charming TuscanVilla with View for Family&Friends
Business host
27 Sept – 2 Oct
4.97 out of 5 average rating, 128 reviews
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Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
Individual host
18–23 Nov
4.98 out of 5 average rating, 116 reviews
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Home in Cortona
Relais Tosca Slow and Rural Life
Individual host
26 Sept – 1 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
Individual host
4–9 Oct
5.0 out of 5 average rating, 115 reviews
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Flat in Montepulciano
Stuart Residence - William Stuart apartment
Business host
4–10 Nov
5.0 out of 5 average rating, 29 reviews
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Villa in Sinalunga
The twigs
Individual host
26–31 Oct
5.0 out of 5 average rating, 97 reviews
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Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
Business host
7–12 Nov
5.0 out of 5 average rating, 120 reviews
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Farm stay in Pienza
Selvoli Farmhouse - La Chiocciola
Business host
11–16 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Guest house in Macciano
Tuscan cottage with an heavenly view
Individual host
30 Oct – 4 Nov
4.97 out of 5 average rating, 246 reviews