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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, 2 beds
4–9 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Apartment in Roccatederighi
Holiday in an antique farm, The Arches
2 bedrooms, 3 beds
3–8 Oct
4.86 out of 5 average rating, 21 reviews
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Guest favourite
Home in Sassofortino
The Casetta by Interhome
2 bedrooms, 1 single bed
23–28 Oct
4.92 out of 5 average rating, 12 reviews
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Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
1–6 Sept
New place to stay
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Superhost
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
1 bedroom, 2 beds
17–22 Oct
4.96 out of 5 average rating, 109 reviews
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Top guest favourite
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, 115 reviews
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Top guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
2 bedrooms, 3 beds
9–14 Oct
4.98 out of 5 average rating, 46 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
3 bedrooms, 4 beds
8–13 Sept
4.99 out of 5 average rating, 137 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds
12–17 Oct
5.0 out of 5 average rating, 39 reviews
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Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms, 4 beds
25–30 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom, 4 beds
8–13 Oct
4.98 out of 5 average rating, 64 reviews
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Home in Roccastrada
Appartamento "A room with a view"
1 bedroom, 3 beds
1–6 Sept
4.92 out of 5 average rating, 79 reviews
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Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds
6–11 Sept
New place to stay
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Top guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms, 2 beds
23–28 Oct
5.0 out of 5 average rating, 32 reviews