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Search results; Over 1,000 homes in Roccastrada
Over 1,000 homes in Roccastrada
Photo 1 of 8
Superhost
Superhost
Tent in Roccastrada
My Olivenhain Glamping
1 bedroom
,
·
2 beds
,
·
1 private bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,073 SGD
Show price breakdown
for 5 nights
$1,073 SGD for 5 nights
,
·
Photo 1 of 29
Top guest favourite
Guest favourite
Holiday home in Roccastrada
Linda's Holiday Home
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
4–9 Oct
4–9 Oct
$1,202 SGD
$973 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
20–25 Oct
20–25 Oct
$3,588 SGD
$3,107 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 141 reviews
5.0 (141)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Sassofortino
The Casetta by Interhome
2 bedrooms
2 bedrooms
,
·
1 single bed
1 single bed
,
·
2 bathrooms
2 bathrooms
1–6 Apr
1–6 Apr
$628 SGD
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for 5 nights
$628 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 12 reviews
4.92 (12)
Photo 1 of 29
Top guest favourite
Guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
17–22 Sept
17–22 Sept
$4,073 SGD
Show price breakdown
for 5 nights
$4,073 SGD for 5 nights
4.99 out of 5 average rating, 138 reviews
4.99 (138)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Monteroni d'Arbia
Discover Tuscany • Peaceful Country Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$1,058 SGD
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for 5 nights
$1,058 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Photo 1 of 29
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
16–21 Sept
16–21 Sept
$5,132 SGD
Show price breakdown
for 5 nights
$5,132 SGD for 5 nights
New place to stay
New
Photo 1 of 29
Guest favourite
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
3–8 Nov
3–8 Nov
$867 SGD
Show price breakdown
for 5 nights
$867 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Photo 1 of 29
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
,
·
5.5 bathrooms
5.5 bathrooms
18–23 Nov
18–23 Nov
$3,054 SGD
$2,612 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 116 reviews
4.98 (116)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Chiusdino
Il Camino: cosy & artfully inspired country house
1 bedroom
1 bedroom
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$979 SGD
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for 5 nights
$979 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 65 reviews
4.98 (65)
Photo 1 of 29
Top guest favourite
Guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
29 Oct – 3 Nov
29 Oct – 3 Nov
$3,706 SGD
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for 5 nights
$3,706 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 36 reviews
5.0 (36)
Photo 1 of 29
Superhost
Superhost
Flat in Montalcino
Wp Relais Argante Apartment
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
24–29 Oct
24–29 Oct
$3,056 SGD
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for 5 nights
$3,056 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Photo 1 of 29
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
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$1,126 SGD
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for 5 nights
$1,126 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 48 reviews
4.98 (48)
Photo 1 of 20
Home in Il Terzo
Casa Bella Vita - Tuscan Escape - Private Terrace
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
16–21 Sept
16–21 Sept
$971 SGD
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for 5 nights
$971 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
6 bedrooms
6 bedrooms
,
·
7 beds
7 beds
,
·
7 bathrooms
7 bathrooms
30 Oct – 4 Nov
30 Oct – 4 Nov
$4,139 SGD
$3,644 SGD
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for 5 nights
Free cancellation
4.99 out of 5 average rating, 116 reviews
4.99 (116)
Photo 1 of 29
Guest favourite
Guest favourite
Apartment in Roccatederighi
Tuscany Retreat & Panoramic Vineyard Views
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
16–21 Sept
16–21 Sept
$1,930 SGD
$1,543 SGD
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for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Photo 1 of 25
Home in Roccastrada
Appartamento "A room with a view"
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
18–23 Sept
18–23 Sept
$565 SGD
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for 5 nights
$565 SGD for 5 nights
4.92 out of 5 average rating, 79 reviews
4.92 (79)
Photo 1 of 29
Guest favourite
Guest favourite
Villa in Sovicille
Farmhouse Podere Il Moro in the nature of Siena
9 bedrooms
9 bedrooms
,
·
16 beds
16 beds
,
·
9 bathrooms
9 bathrooms
16–21 Sept
16–21 Sept
$7,513 SGD
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for 5 nights
$7,513 SGD for 5 nights
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Photo 1 of 29
Top guest favourite
Guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
2 bathrooms
2 bathrooms
23–28 Oct
23–28 Oct
$1,691 SGD
$1,477 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 33 reviews
5.0 (33)
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