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Search results; Over 1,000 homes in Castel San Gimignano

Superhost
Flat in Castel San Gimignano
Girasole large apartment in a Tuscan village
1 bedroom, 3 beds, 1 private bathroom
16–21 Sept, Individual host
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4.77 out of 5 average rating, 118 reviews
Guest favourite
Apartment in Castel San Gimignano
DeCipressi | Casa Gelsomino
Individual host
25–30 Sept
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in San Gimignano
"Vernaccia" by Podere la Fonte
Individual host
26 Sept – 1 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Villa in Volterra
Luxury A/C Villa + Annex with Jacuzzi + Pool, Chef
Business host
11–17 Oct
5.0 out of 5 average rating, 35 reviews
Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
20–25 Sept
4.95 out of 5 average rating, 178 reviews
Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
Individual host
10–15 Nov
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in San Gimignano
Tuscan Countryside Hideaway • La Casa Rossa n.3
Business host
18–23 Sept
Top guest favourite
Home in Volterra
Vacation home with private pool, view
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
9–14 Sept
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Home in Montaione
Cercis - La Palmierina
Individual host
24–29 Oct
4.96 out of 5 average rating, 146 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
19–24 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
10–15 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Volterra
Charming Tuscan Villa with pool
Individual host
20–25 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
9–14 Sept
4.99 out of 5 average rating, 114 reviews
Top guest favourite
Villa in Tignano
Villa Isabella
Individual host
20–25 Sept
4.96 out of 5 average rating, 208 reviews
Top guest favourite
Home in Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Colle di Val d'Elsa
Charming farmhouse "LA PIEVE - Duke Suite
Business host
1–6 Oct
4.98 out of 5 average rating, 48 reviews