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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
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
Flat in Montepulciano
Suite for 3 · Heart of Old Montepulciano + AC
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
New place to stay
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
A view from the gate, Montepulciano.
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 322 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
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, 231 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
Holiday home in Monticchiello
Tuscan country house with views of Pienza
3 bedrooms, 4 beds, 3 bathrooms
16–21 Jul
5.0 out of 5 average rating, 33 reviews
Flat in Montepulciano
Serena Montepulciano Penthouse
2 bedrooms, 3 beds, 1 bathroom
15–20 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Farm stay in Montalcino
Hilltop farmhouse with 360° Val d’Orcia views
2 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
4.98 out of 5 average rating, 43 reviews
Home in Montepulciano
Walk to cafés, shops, and bike rentals
2 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
New place to stay
Top guest favourite
Flat in Montepulciano
Vaulted ceilings and contemporary design in Montepulciano
2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Flat in Montepulciano
17th-century Tuscan style near a vineyard
1 bedroom, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 209 reviews
Top guest favourite
Flat in Montepulciano
Renovated 1300s building with lake views
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jul
4.97 out of 5 average rating, 266 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
Apartment in Siena
Penthouse overlooking Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
19–24 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Asciano
Hilltop garden in the Crete Senesi
2 bedrooms, 4 beds, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 317 reviews
Top guest favourite
Guest house in Montefollonico
Stone farmhouse with Val d’Orcia views
1 bedroom, 1 bed, 1 bathroom
23–28 Jul
4.98 out of 5 average rating, 130 reviews