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Search results; Over 1,000 homes in Montepulciano

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
La Piazzetta - Cozy open space in the historic center of Montepulciano
5.0 out of 5 average rating, 508 reviews, 2 beds, 1 bathroom
15–20 Jul
Flat in Montepulciano
Suite for 3 · Heart of Old Montepulciano + AC
New place to stay, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Flat in Montepulciano
Authentic Tuscany House in the Center 120mq
4.95 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 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
Guest house in Macciano
Tuscan cottage with an heavenly view
4.97 out of 5 average rating, 231 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
4.97 out of 5 average rating, 322 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Apartment in Montepulciano
The walnut tree view, Montepulciano
5.0 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Oct – 5 Nov
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
15–20 Jul
Top guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Flat in Montepulciano
Serena Montepulciano Penthouse
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
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
Charming House in Montepulciano
4.93 out of 5 average rating, 153 reviews, 2 bedrooms, 5 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Montepulciano
Mery’s House | Design stay in Montepulciano
5.0 out of 5 average rating, 80 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Villa in Sinalunga
The twigs
5.0 out of 5 average rating, 89 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Oct
Top guest favourite
Flat in Montepulciano
The source
5.0 out of 5 average rating, 209 reviews, 1 bedroom, 3 beds, 2 bathrooms
30 Oct – 4 Nov
Top guest favourite
Flat in Montepulciano
Casa Ricci Apartment in a 14th-century building
4.97 out of 5 average rating, 266 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
4.97 out of 5 average rating, 123 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Nov
Top guest favourite
Flat in Montepulciano
WiFiFiber LargeApartment with view inMontepulciano
5.0 out of 5 average rating, 50 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Nov – 6 Dec