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Search results; Over 1,000 homes in Roccastrada

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Superhost
Tent in Roccastrada
Bell tent in Tuscany
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
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Top guest favourite
Holiday home in Roccastrada
Linda's Holiday Home
2 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
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, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Roccastrada
Appartamento "A room with a view"
1 bedroom, 3 beds, 1 bathroom
1–6 Sept
4.92 out of 5 average rating, 79 reviews
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Top guest favourite
Room in Gavorrano
B&B S. Beatrice, Camera N. 2
1 queen bed, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Apartment in Montieri
Cupiano Farm "Querciolettaia/Legnaio"
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
4.96 out of 5 average rating, 55 reviews
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Guest favourite
Apartment in Roccatederighi
Tuscany Retreat & Panoramic Vineyard Views
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 10 reviews
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Superhost
Flat in Monticiano
small apartment
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 60 reviews
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Flat in Roccastrada
Noble - Borgo la Civitella by Interhome
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.25 out of 5 average rating, 4 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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Flat in Roccastrada
Apartment with private veranda
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Le Coste
Casa Vacanze In Maremma Il Seccatoio
2 bedrooms, 2 beds, 1 bathroom
23–30 Sept
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Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
2 bedrooms, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.96 out of 5 average rating, 26 reviews
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Home in Roccastrada
La Casetta dei Pereti
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
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Home in Torniella
Casa Reasco
5 bedrooms, 4 beds, 5 bathrooms
19–26 Sept
4.92 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Monteroni d'Arbia
Villa Canina - charm and rurality in the Crete Senesi
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 10 reviews
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Flat in Montemassi
Poggio Piero Estate 1
1 bedroom, 1 sofa bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom, 4 beds, 1 bathroom
8–13 Oct
4.98 out of 5 average rating, 64 reviews
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Top guest favourite
Flat in Roccastrada
Apartment in a wine estate
1 bedroom, 1 bed, 1 bathroom
15–22 May
5.0 out of 5 average rating, 30 reviews