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Search results; Over 1,000 homes in Montepulciano

Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Nov
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4.97 out of 5 average rating, 321 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
5.0 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 3 bathrooms
11–16 Aug
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
11–16 Jul
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
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, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Guest suite in Cetona
Cozy country house
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 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
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 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 Sinalunga
The twigs
5.0 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 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 San Quirico d'Orcia
Panoramic Apartment in Center Dimora del Poggio
4.99 out of 5 average rating, 94 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Guest favourite
Flat in Montepulciano
Authentic Tuscany House in the Center 120mq
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
4.98 out of 5 average rating, 112 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
20–25 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 Monticchiello
Casa Bonari - a paradise for the eyes
4.97 out of 5 average rating, 181 reviews, 3 bedrooms, 4 beds, 2 bathrooms
11–16 Aug
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
Dimora dell'Erbe - Rooftop Apartment
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Oct