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Search results; Over 1,000 homes in Roccastrada

Top guest favourite
Loft in Roccastrada
"Casa Chiassarello" with pool
1 bedroom, 1 bed, 1 private bathroom
2–7 May
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5.0 out of 5 average rating, 67 reviews
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
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
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
Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
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
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Monteroni d'Arbia
Discover Tuscany • Peaceful Country Retreat
2 bedrooms, 2 beds, 1 bathroom
15–20 Oct
5.0 out of 5 average rating, 18 reviews
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
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
3 bedrooms, 4 beds, 4 bathrooms
16–21 Sept
4.99 out of 5 average rating, 138 reviews
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, 115 reviews
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
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
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.97 out of 5 average rating, 327 reviews
Guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
3 bedrooms, 4 beds, 2 bathrooms
17–22 Nov
4.97 out of 5 average rating, 187 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 98 reviews
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