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Search results; Over 1,000 homes in Montepulciano

Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
4 bedrooms, 5 beds, 2.5 private bathrooms
4–9 Nov
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4.97 out of 5 average rating, 123 reviews
Top guest favourite
Guest house in Macciano
Tuscan cottage with an heavenly view
4.97 out of 5 average rating, 230 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
Top guest favourite
Villa in Chianciano Terme
Villa with View for Family & Friends, in Tuscany
4.97 out of 5 average rating, 126 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
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
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
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
4.98 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
4.97 out of 5 average rating, 321 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Nov
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
Top guest favourite
Tower in San Quirico d'Orcia
Luxurious Medieval Tower & Private Concierge
5.0 out of 5 average rating, 113 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Aug
Top guest favourite
Farm stay in Montalcino
Tuscan Farmhouse ~ Magic Sunsets ~ 360° view
4.98 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 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, 507 reviews, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Apartment in Pienza
Mascagni Farmhouse in Val d'Orcia, Pienza
5.0 out of 5 average rating, 154 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
Top guest favourite
Guest suite in Cetona
Cozy country house
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Aug – 1 Sept
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
Guest favourite
Flat in Montepulciano
Montepulciano – La Botte | Romantic, AC & Parking
4.85 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
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
11–16 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 Asciano
Celeste – The color of the summer sky in Tuscany
4.97 out of 5 average rating, 315 reviews, 2 bedrooms, 4 beds, 1 bathroom
10–15 Jul
Top guest favourite
Villa in Sinalunga
The twigs
5.0 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Oct