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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
5.0 out of 5 average rating, 508 reviews, 2 beds, 1 bathroom
16–21 Jul
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
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
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 3 bathrooms
16–21 Jul
Top guest favourite
Guest house in Macciano
Tuscan views, pool, and pizza oven
4.97 out of 5 average rating, 231 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
Home in Montepulciano
Casa dolce casa
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
20–25 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
Superhost
Flat in Scrofiano
Tuscan countryside views and a fireplace
New place to stay, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Flat in Montepulciano
Top-floor views beyond the city walls
4.99 out of 5 average rating, 296 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov
Top guest favourite
Flat in Montepulciano
Renovated 1300s building with lake views
4.97 out of 5 average rating, 266 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
Top guest favourite
Apartment in San Quirico d'Orcia
Panoramic views in Val d’Orcia’s heart
4.99 out of 5 average rating, 96 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Top guest favourite
Guest house in Montefollonico
Stone farmhouse with Val d’Orcia views
4.98 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Top guest favourite
Flat in Montepulciano
Sofia in Montepulciano
4.99 out of 5 average rating, 72 reviews, 1 bedroom, 1 bathroom
23–28 Oct
Top guest favourite
Flat in Montepulciano
Vaulted ceilings and contemporary design in Montepulciano
5.0 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Apartment in Asciano
Celeste – The color of the summer sky in Tuscany
4.97 out of 5 average rating, 317 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Aug
Top guest favourite
Farm stay in Montalcino
Hilltop farmhouse with 360° Val d’Orcia views
4.98 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 2 bathrooms
31 Jul – 5 Aug
Guest favourite
Flat in Montepulciano
Montepulciano – La Botte | Romantic, AC & Parking
4.87 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Sept