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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
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
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
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
Farm stay in Pienza
Selvoli Farmhouse - La Chiocciola
4.97 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 3 bathrooms
15–20 Jul
Top guest favourite
Guest house in Montefollonico
Casale Santa Barbara - Exclusive Apartment
4.98 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
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
Home in Castiglion Fiorentino
Hidden gem in Tuscany
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 3 bathrooms
11–16 Aug
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
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
Apartment in Pienza
A 1500s barn on an organic farm
5.0 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
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
16–21 Jul
Top guest favourite
Villa in Chianciano Terme
Hot tub with a view in Tuscany
4.97 out of 5 average rating, 126 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Castiglione del Lago
Hilltop farmhouse with pool and panoramic views
4.93 out of 5 average rating, 152 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Oct
Top guest favourite
Tiny home in Pienza
Selvoli Farmhouse – The School
4.93 out of 5 average rating, 68 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Oct
Top guest favourite
Serviced apartment in Bettolle
Historic Apartment at Villa Vignacce
4.97 out of 5 average rating, 59 reviews, 2 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
Top guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
4.97 out of 5 average rating, 183 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
Top guest favourite
Guest suite in Cetona
Private pool and garden in Tuscany
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Villa in Poggioferro
Poggio among the olive trees
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 3 beds, 2 bathrooms
6–11 Oct