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Search results; Over 1,000 homes in La Gruccia

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Top guest favourite
Flat in La Gruccia
San Raffaele Estate
1 bedroom, 2 beds, 1 private bathroom
19–24 Oct, Individual host
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4.97 out of 5 average rating, 38 reviews
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Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
Business host
16–21 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 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
Individual host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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Flat in Poggibonsi
Suite Gaia With Holistic Rural wellness Access
Business host
1–6 Oct
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Villa in Poggibonsi
Castagneto Holiday house
Individual host
3–10 Oct
4.82 out of 5 average rating, 11 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 143 reviews
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Superhost
Flat in Poggibonsi
Sole: Rustic Escape Tuscany private park @ Chianti
Individual host
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
Business host
1–6 May
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Villa in San Gimignano
Fabulous 3Br Villa with 360° Views!
Individual host
3–8 May
4.95 out of 5 average rating, 75 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
27 Oct – 1 Nov
4.95 out of 5 average rating, 57 reviews
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Top guest favourite
Apartment in Siena
Luxury penthouse with a view of Piazza del Campo
Individual host
25–30 Oct
5.0 out of 5 average rating, 23 reviews
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Superhost
Flat in Poggibonsi
Il Casale di Villore, Poggibonsi, Siena, Tuscany, Prugnolo Apt.
Business host
20–25 Oct
5.0 out of 5 average rating, 9 reviews