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Search results; Over 1,000 homes in Montepulciano

Descriptions are based on details hosts provide
Top guest favourite
Loft in Montepulciano
The little house in Via Fiorita Tuscan charm
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.96 out of 5 average rating, 226 reviews
Guest favourite
Flat in Montepulciano
Authentic Tuscany House in the Center 120mq
2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
4.95 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Montepulciano
Spectacular hill views with designer furniture
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 322 reviews
Guest favourite
Flat in Montepulciano
Wine-inspired retreat near the historic center
2 bedrooms, 2 beds, 1 bathroom
2–7 Sept
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Loft in Montepulciano
Stone walls and a fireplace near vineyards
2 beds, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 508 reviews
Top guest favourite
Flat in Montepulciano
Rooftop terraces over Montepulciano’s roofs
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Farm stay in Pienza
Selvoli Farmhouse - La Chiocciola
3 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms, 4 beds, 3 bathrooms
16–21 Jul
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Villa in Sarteano
Stone farmhouse in Val D'Orcia
5 bedrooms, 9 beds, 6 bathrooms
17–22 Sept
4.97 out of 5 average rating, 156 reviews
Top guest favourite
Farm stay in Montepulciano
Tuscan villa among olive trees and vineyards
3 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Apartment in Montepulciano
The walnut tree view, Montepulciano
1 bedroom, 1 double bed, 1 bathroom
31 Oct – 5 Nov
5.0 out of 5 average rating, 121 reviews
Top guest favourite
Villa in Chianciano Terme
Charming Tuscan Villa with View forFamily&Friends
2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.97 out of 5 average rating, 126 reviews
Top guest favourite
Villa in Montepulciano
Vineyard villa with pool and hot tub
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Nov
4.97 out of 5 average rating, 123 reviews
Top guest favourite
Apartment in Montepulciano
High wooden ceilings with valley-view terrace
2 bedrooms, 2 beds, 2 bathrooms
20–25 Oct
4.97 out of 5 average rating, 340 reviews
Top guest favourite
Villa in Pienza
17th-century farmhouse amid olive groves
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Montepulciano
The source
1 bedroom, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 209 reviews
Top guest favourite
Guest house in Macciano
Tuscan views, pool, and pizza oven
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.97 out of 5 average rating, 232 reviews
Guest favourite
Home in Montepulciano
Two connected apartments near wineries
4 bedrooms, 8 beds, 4 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 9 reviews