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Search results; Over 1,000 homes in Poggibonsi

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Guest favourite
Apartment in Poggibonsi
PODERE VAL DI GALLO, CHIANTI, SIENA
2 bedrooms, 2 beds, 1 private bathroom
11–16 Oct, Business host
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4.74 out of 5 average rating, 277 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
Individual host
6–11 Nov
4.99 out of 5 average rating, 97 reviews
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Top guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
19–24 Sept
4.95 out of 5 average rating, 151 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
5–10 Sept
New place to stay
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
6–11 Oct
5.0 out of 5 average rating, 129 reviews
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Top guest favourite
Apartment in San Gimignano
Casaglia Residence
Individual host
5–10 Oct
4.97 out of 5 average rating, 75 reviews
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Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 385 reviews
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Guest favourite
Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
Individual host
9–14 Sept
5.0 out of 5 average rating, 8 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
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Flat in Poggibonsi
Modern and bright studio apartment! New!
Individual host
7–12 Oct
5.0 out of 5 average rating, 17 reviews