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Search results; Over 1,000 homes in Roccastrada
Over 1,000 homes in Roccastrada
Photo 1 of 6
Superhost
Superhost
Tent in Roccastrada
Bell tent in Tuscany
1 bedroom
,
·
1 bed
,
·
1 bathroom
1–6 Sept
1–6 Sept
$1,245 SGD
Show price breakdown
for 5 nights
$1,245 SGD for 5 nights
,
·
Photo 1 of 6
Top guest favourite
Guest favourite
Holiday home in Roccastrada
Linda's Holiday Home
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
4–9 Sept
4–9 Sept
$1,182 SGD
$963 SGD
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for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Photo 1 of 6
Guest favourite
Guest favourite
Apartment in Roccatederighi
Holiday in an antique farm, The Arches
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
3–8 Oct
3–8 Oct
$1,415 SGD
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for 5 nights
$1,415 SGD for 5 nights
4.86 out of 5 average rating, 21 reviews
4.86 (21)
Photo 1 of 6
Guest favourite
Guest favourite
Home in Sassofortino
The Casetta by Interhome
2 bedrooms
2 bedrooms
,
·
1 single bed
1 single bed
23–28 Oct
23–28 Oct
$590 SGD
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for 5 nights
$590 SGD for 5 nights
4.92 out of 5 average rating, 12 reviews
4.92 (12)
Photo 1 of 6
Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
1–6 Sept
1–6 Sept
$979 SGD
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for 5 nights
$979 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 6
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
1–6 Sept
1–6 Sept
$4,060 SGD
Show price breakdown
for 5 nights
$4,060 SGD for 5 nights
New place to stay
New
Photo 1 of 6
Superhost
Superhost
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
1 bedroom
1 bedroom
,
·
2 beds
2 beds
17–22 Oct
17–22 Oct
$1,277 SGD
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for 5 nights
$1,277 SGD for 5 nights
4.96 out of 5 average rating, 109 reviews
4.96 (109)
Photo 1 of 6
Top guest favourite
Guest favourite
Farm stay in San Quirico d'Orcia
Podere Pereti Nuovi – Modern Tuscan Villa
5 bedrooms
5 bedrooms
,
·
5 double beds
5 double beds
18–23 Nov
18–23 Nov
$3,041 SGD
$2,708 SGD
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for 5 nights
4.98 out of 5 average rating, 115 reviews
4.98 (115)
Photo 1 of 6
Top guest favourite
Guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
9–14 Oct
9–14 Oct
$1,135 SGD
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for 5 nights
$1,135 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Photo 1 of 6
Top guest favourite
Guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
12–17 Oct
12–17 Oct
$1,397 SGD
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for 5 nights
$1,397 SGD for 5 nights
4.98 out of 5 average rating, 82 reviews
4.98 (82)
Photo 1 of 6
Top guest favourite
Guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
8–13 Sept
8–13 Sept
$3,733 SGD
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for 5 nights
$3,733 SGD for 5 nights
4.99 out of 5 average rating, 137 reviews
4.99 (137)
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
1–6 Sept
1–6 Sept
$2,644 SGD
$2,380 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 6
Top guest favourite
Guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
12–17 Oct
12–17 Oct
$1,766 SGD
$1,396 SGD
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for 5 nights
5.0 out of 5 average rating, 39 reviews
5.0 (39)
Photo 1 of 6
Superhost
Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
25–30 Sept
25–30 Sept
$2,934 SGD
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for 5 nights
$2,934 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 6
Top guest favourite
Guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
1–6 Sept
1–6 Sept
$8,887 SGD
$7,554 SGD
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for 5 nights
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Photo 1 of 6
Top guest favourite
Guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom
1 bedroom
,
·
4 beds
4 beds
8–13 Oct
8–13 Oct
$1,017 SGD
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for 5 nights
$1,017 SGD for 5 nights
4.98 out of 5 average rating, 64 reviews
4.98 (64)
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Home in Roccastrada
Appartamento "A room with a view"
1 bedroom
1 bedroom
,
·
3 beds
3 beds
1–6 Sept
1–6 Sept
$568 SGD
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for 5 nights
$568 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 79 reviews
4.92 (79)
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Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
6–11 Sept
6–11 Sept
$2,889 SGD
$2,370 SGD
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for 5 nights
New place to stay
New
Photo 1 of 6
Top guest favourite
Guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
23–28 Oct
23–28 Oct
$1,489 SGD
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for 5 nights
$1,489 SGD for 5 nights
5.0 out of 5 average rating, 32 reviews
5.0 (32)
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