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Search results; Over 1,000 homes in Roccastrada

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Superhost
Tent in Roccastrada
My Olivenhain Glamping
1 bedroom, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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Top guest favourite
Holiday home in Roccastrada
Linda's Holiday Home
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
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Guest favourite
Home in Sassofortino
The Casetta by Interhome
2 bedrooms, 1 single bed, 2 bathrooms
1–6 Apr
4.92 out of 5 average rating, 12 reviews
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Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
3 bedrooms, 4 beds, 4 bathrooms
17–22 Sept
4.99 out of 5 average rating, 138 reviews
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Top guest favourite
Home in Monteroni d'Arbia
Discover Tuscany • Peaceful Country Retreat
2 bedrooms, 2 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 18 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
New place to stay
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Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
2 bedrooms, 2 beds, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 26 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, 5.5 bathrooms
18–23 Nov
4.98 out of 5 average rating, 116 reviews
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Top guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom, 4 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 65 reviews
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Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms, 4 beds, 3 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 reviews
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Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms, 4 beds, 3 bathrooms
24–29 Oct
5.0 out of 5 average rating, 4 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, 1 bathroom
23–28 Oct
4.98 out of 5 average rating, 48 reviews
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Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms, 7 beds, 7 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 116 reviews
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Guest favourite
Apartment in Roccatederighi
Tuscany Retreat & Panoramic Vineyard Views
3 bedrooms, 3 beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Roccastrada
Appartamento "A room with a view"
1 bedroom, 3 beds, 1 bathroom
18–23 Sept
4.92 out of 5 average rating, 79 reviews
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Guest favourite
Villa in Sovicille
Farmhouse Podere Il Moro in the nature of Siena
9 bedrooms, 16 beds, 9 bathrooms
16–21 Sept
4.95 out of 5 average rating, 20 reviews
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Top guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms, 2 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 33 reviews