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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
Wine-inspired retreat near the historic center
4.87 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Sept
Guest favourite
Flat in Montepulciano
Elegant Tuscan home in the historic center
4.95 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Flat in Montepulciano
Spectacular hill views with designer furniture
4.97 out of 5 average rating, 322 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Loft in Montepulciano
Stone walls and a fireplace near vineyards
5.0 out of 5 average rating, 508 reviews, 2 beds, 1 bathroom
16–21 Jul
Top guest favourite
Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
5.0 out of 5 average rating, 115 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Farm stay in Pienza
Selvoli Farmhouse - La Chiocciola
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Holiday home in Monticchiello
Tuscan country house with views of Pienza
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 3 bathrooms
16–21 Jul
Top guest favourite
Home in Lucignano
Historic Tuscan farmhouse with pool and olive groves
4.98 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
Top guest favourite
Farm stay in Montepulciano
Tuscan villa among olive trees and vineyards
4.95 out of 5 average rating, 110 reviews, 3 bedrooms, 3 beds, 1 bathroom
18–23 Oct
Top guest favourite
Villa in Sarteano
Stone farmhouse in Val D'Orcia
4.97 out of 5 average rating, 156 reviews, 5 bedrooms, 9 beds, 6 bathrooms
17–22 Sept
Top guest favourite
Apartment in Montepulciano
Hilltop terrace with Val d’Orcia views
5.0 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Oct – 5 Nov
Top guest favourite
Villa in Chianciano Terme
Hot tub with a view in Tuscany
4.97 out of 5 average rating, 126 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Montepulciano
17th-century Tuscan style near a vineyard
5.0 out of 5 average rating, 209 reviews, 1 bedroom, 3 beds, 2 bathrooms
30 Oct – 4 Nov
Top guest favourite
Apartment in Asciano
Hilltop garden in the Crete Senesi
4.97 out of 5 average rating, 317 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Aug
Top guest favourite
Apartment in Montepulciano
Residence In cerca d'Autore
4.97 out of 5 average rating, 340 reviews, 2 bedrooms, 2 beds, 2 bathrooms
20–25 Oct
Top guest favourite
Villa in Montepulciano
Vineyard villa with pool and hot tub
4.97 out of 5 average rating, 123 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Nov
Top guest favourite
Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
4.99 out of 5 average rating, 109 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Top guest favourite
Guest house in Macciano
Tuscan views, pool, and pizza oven
4.97 out of 5 average rating, 232 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov