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Search results; Over 1,000 homes in Montepulciano

Guest favourite
Villa in Montepulciano
Villa in Montepulciano with a Pool
2 bedrooms, 4 beds, 2 private bathrooms
27 Oct – 1 Nov, Business host
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4.92 out of 5 average rating, 148 reviews
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, 327 reviews
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
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, 55 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
Individual host
15–20 Sept
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Business host
30 Oct – 4 Nov
4.97 out of 5 average rating, 125 reviews
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
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
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
Top guest favourite
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
Flat in Montepulciano
Dimora Nobile
Individual host
11–16 Sept
New place to stay
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, 114 reviews
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
Top guest favourite
Flat in Montepulciano
The source
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
Business host
7–12 Nov
5.0 out of 5 average rating, 120 reviews
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
Top guest favourite
Villa in Castiglion Fiorentino
Beautiful and cozy country-house, sleeps 11
Individual host
20–25 Sept
5.0 out of 5 average rating, 25 reviews
Home in Monticchiello
Casa Bianchini: ancient memories
Individual host
31 Oct – 5 Nov
Bed and breakfast in Siena
Abbadia Sicille Relais, Royal Suite with Jacuzzi
Business host
21–26 Oct
5.0 out of 5 average rating, 4 reviews