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Search results; Over 1,000 homes in Montepulciano

Top guest favourite
Holiday home in Montepulciano
Stuart Jasmine central, panoramic top location
1 bedroom, 1 bed, 1 private bathroom
1–6 Jul
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4.92 out of 5 average rating, 204 reviews
Top guest favourite
Farm stay in Monticchiello
Podere Lamino, Val d'Orcia, Pienza
4.99 out of 5 average rating, 67 reviews, 4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
Guest favourite
Farm stay in Cortona
Relaxing-unspoiled country place La Valle...
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Superhost
Farm stay in Monte San Savino
(M) Luxury Villa | Infinity Pool, Sauna & Cinema
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 9 beds, 5.5 bathrooms
12–17 Aug
Top guest favourite
Loft in Montepulciano
La Piazzetta - Cozy open space in the historic center of Montepulciano
5.0 out of 5 average rating, 506 reviews, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Apartment in Asciano
Celeste – The color of the summer sky in Tuscany
4.97 out of 5 average rating, 314 reviews, 2 bedrooms, 4 beds, 1 bathroom
10–15 Jul
Top guest favourite
Flat in Cantagallina Alta
Il Gelsomino, apartment between Tuscany and Umbria
4.99 out of 5 average rating, 87 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
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
Guest suite in Cetona
Cozy country house
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Aug
Top guest favourite
Flat in Montepulciano
The source
5.0 out of 5 average rating, 208 reviews, 1 bedroom, 3 beds, 2 bathrooms
30 Oct – 4 Nov
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 4 bathrooms
21–26 Jul
Top guest favourite
Flat in Montepulciano
Montepulciano Historic Center
4.99 out of 5 average rating, 295 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov
Top guest favourite
Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct
Top guest favourite
Flat in Lucignano
Palazzo Trapani Luxury Residence
5.0 out of 5 average rating, 34 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
Top guest favourite
Apartment in Asciano
Casa Biancospino Crete Senesi | Podere Fossaccio
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Farm stay in Montepulciano
detached villa in private garden
4.88 out of 5 average rating, 17 reviews, 2 bedrooms, 6 beds, 2 bathrooms
11–16 Jul
Villa in Montepulciano
Podere Pisinano- Tuscan villa with swimming pool
5 bedrooms, 6 beds, 5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Cortona
Breathtaking views: Historic House w/Terrace & BBQ
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
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
11–16 Nov