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Search results; Over 1,000 homes in Montepulciano

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Top guest favourite
Villa in Montepulciano
A paradise in Montepulciano...
5 bedrooms, 5 beds, 4 private bathrooms
8–13 Oct, Individual host
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4.96 out of 5 average rating, 168 reviews
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Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
Individual host
30 Oct – 4 Nov
4.97 out of 5 average rating, 328 reviews
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Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
Individual host
16–21 Sept
4.98 out of 5 average rating, 49 reviews
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Top guest favourite
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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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, 56 reviews
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Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Business host
30 Oct – 4 Nov
4.97 out of 5 average rating, 126 reviews
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Top guest favourite
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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Top guest favourite
Home in Cortona
Relais Tosca Slow and Rural Life
Individual host
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
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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Top guest favourite
Villa in Chianciano Terme
Charming Villa in Montepulciano for Fam & Friends
Business host
27 Sept – 2 Oct
4.97 out of 5 average rating, 129 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, 116 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, 116 reviews
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Top guest favourite
Farm stay in Sinalunga
Villa Panorama near Siena Tuscany
Business host
17–23 Sept
5.0 out of 5 average rating, 54 reviews
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Top guest favourite
Villa in Ambra
Chianti Villa in Tuscany near Siena and Arezzo
Business host
8–13 Oct
4.99 out of 5 average rating, 151 reviews
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Top guest favourite
Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
Business host
7–12 Nov
5.0 out of 5 average rating, 121 reviews
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Top guest favourite
Flat in Montepulciano
The source
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 215 reviews
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Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 67 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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Top guest favourite
Flat in Castiglioncello del Trinoro
Stunning Tuscan apartment in 14 Century Palazzo
Individual host
19–24 Oct
5.0 out of 5 average rating, 367 reviews