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Search results; Over 1,000 homes in Montepulciano

Flat in Montepulciano
Casa Evelina - Incredible View, Central Location
3 bedrooms, 3 beds, 2 private bathrooms
23–28 Oct
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4.82 out of 5 average rating, 121 reviews
Guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
3 bedrooms, 4 beds
17–22 Nov
4.97 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
2 bedrooms, 3 beds
30 Oct – 4 Nov
4.97 out of 5 average rating, 327 reviews
Top guest favourite
Apartment in Montepulciano
The walnut tree view, Montepulciano
1 bedroom, 1 double bed
3–8 Nov
5.0 out of 5 average rating, 136 reviews
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms, 4 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 reviews
Villa in Pienza
Pennella | Private villa with panoramic pool
4 bedrooms, 6 beds
10–17 Oct
Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
4 bedrooms, 4 queen beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 67 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds
6–11 Oct
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Montepulciano
The source
1 bedroom, 3 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 215 reviews
Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
4 bedrooms, 5 beds
30 Oct – 4 Nov
4.97 out of 5 average rating, 126 reviews
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms, 5 double beds
18–23 Nov
4.98 out of 5 average rating, 116 reviews
Top guest favourite
Villa in Chianciano Terme
Charming Tuscan Villa with View forFamily&Friends
2 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 129 reviews
Guest favourite
Home in Montepulciano
Spacious Tuscan Home – 2 Connected Apts, 4BR/4BA
4 bedrooms, 8 beds
10–15 Nov
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Montepulciano
Montepulciano – La Botte | Romantic, AC & Parking
2 bedrooms, 2 double beds
1–6 Nov
4.94 out of 5 average rating, 49 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds
15–20 Sept
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds
26–31 Oct
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
1 bedroom, 2 beds
4–9 Oct
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Home in Cortona
Relais Tosca Slow and Rural Life
2 bedrooms, 2 double beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds
30 Oct – 4 Nov
4.99 out of 5 average rating, 115 reviews