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Search results; Over 1,000 homes in Roccastrada

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Home in Roccastrada
Casale Vezzoli with pool
2 bedrooms, 3 beds, 1 private bathroom
3–10 Oct
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3.5 out of 5 average rating, 4 reviews
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Holiday home in Roccastrada
Linda's Holiday Home
2 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Roccastrada
Suite-apartment in Maremma
2 bedrooms, 3 beds
21–26 Jan
4.95 out of 5 average rating, 19 reviews
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Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Room in Gavorrano
B&B S. Beatrice, Camera N. 1
1 double bed
4–9 Oct
4.95 out of 5 average rating, 40 reviews
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Top guest favourite
Apartment in Montieri
Cupiano Farm "Querciolettaia/Legnaio"
2 bedrooms, 4 beds
1–6 Oct
4.96 out of 5 average rating, 57 reviews
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Flat in Montemassi
Poggio Piero Estate 1
1 bedroom, 1 sofa bed
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Sassofortino
The Casetta by Interhome
2 bedrooms, 1 single bed
1–6 Apr
4.92 out of 5 average rating, 12 reviews
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Home in Monteroni d'Arbia
Discover Tuscany • Peaceful Country Retreat
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Villa in Siena
Exclusive Villa Mami
6 bedrooms, 6 beds
18–23 Oct
5.0 out of 5 average rating, 25 reviews
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Flat in Siena
San Francesco Penthouse
3 bedrooms, 3 beds
26–31 Oct
4.98 out of 5 average rating, 88 reviews
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Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms, 5 double beds
18–23 Nov
4.98 out of 5 average rating, 116 reviews
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Flat in Roccastrada
Apartment with private veranda
2 bedrooms, 3 beds
10–15 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Montepulciano
Montepulciano – La Botte | Romantic, AC & Parking
2 bedrooms, 2 double beds
1–6 Nov
4.95 out of 5 average rating, 55 reviews
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Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds
21–26 Oct
4.95 out of 5 average rating, 42 reviews
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Farm stay in Montalcino
Farmhouse surrounded by vineyards - Salvia
2 bedrooms, 4 beds
18–23 Oct
4.98 out of 5 average rating, 49 reviews
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Home in CIVITELLA MARITTIMA
TUSCANY, VIOLAPO COTTAGE, B&B
3 bedrooms, 3 double beds
1–6 Oct
4.75 out of 5 average rating, 8 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
7–12 Oct
5.0 out of 5 average rating, 3 reviews