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Search results; Over 1,000 homes in Poggibonsi

Top guest favourite
Castle in Poggibonsi
Castle with panoramic pool in the heart of Tuscany
5 bedrooms, 6 beds, 5.5 private bathrooms
19–24 Oct, Business host
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4.97 out of 5 average rating, 72 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
Villa in Poggibonsi
Villa L'Olivo w/Private pool (Close San Gimignano)
Individual host
6–11 Nov
4.99 out of 5 average rating, 98 reviews
Guest favourite
Apartment in Poggibonsi
Gallery Apartment near Chianti
Individual host
11–16 Oct
4.95 out of 5 average rating, 151 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
2–7 Sept
4.98 out of 5 average rating, 60 reviews
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
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
Individual host
21–26 Sept
5.0 out of 5 average rating, 129 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 207 reviews
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
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
Top guest favourite
Apartment in San Gimignano
Casaglia Residence
Individual host
5–10 Oct
4.97 out of 5 average rating, 75 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
Flat in Poggibonsi
Laura Chianti Holidays
Individual host
9–14 Nov
4.98 out of 5 average rating, 338 reviews
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, 113 reviews
Top guest favourite
Villa in Impruneta
Private Estate - Personal Concierge & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
Top guest favourite
Apartment in Colle di Val d'Elsa
Florence & Siena • Terrace • Private Parking • A/C
Individual host
19–24 Oct
5.0 out of 5 average rating, 27 reviews
Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
2–7 Sept
5.0 out of 5 average rating, 3 reviews