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Search results; Over 1,000 homes in Poggibonsi

Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 private bathrooms
9–14 Nov, Individual host
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4.98 out of 5 average rating, 338 reviews
Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
Business host
19–24 Oct
4.97 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
11–16 Oct
4.95 out of 5 average rating, 151 reviews
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, 99 reviews
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
Top guest favourite
Apartment in Poggibonsi
Casa Amaryllis
Individual host
10–15 Oct
4.98 out of 5 average rating, 289 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
21–26 Sept
5.0 out of 5 average rating, 130 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 49 reviews
Guest favourite
Flat in Poggibonsi
Cozy tourist house for 4 guests, top relaxation!
Individual host
11–16 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Poggibonsi
cate house
Individual host
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Holiday home in Poggibonsi
Podere Chiocciola, 2 bedroom apartment
Individual host
6–11 Sept
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
Business host
23–28 Oct
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Gavignano
Poggio Massiccioli
Individual host
30 Oct – 4 Nov
4.92 out of 5 average rating, 386 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in San Gimignano
Casaglia Residence
Individual host
5–10 Oct
4.97 out of 5 average rating, 75 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
3–8 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
Individual host
22–27 Sept
5.0 out of 5 average rating, 11 reviews