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

Home in Castel San Gimignano
Rustic Cavernous by Interhome
3 bedrooms, 4 beds, 2 private bathrooms
14–19 Sept, Business host
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4.84 out of 5 average rating, 25 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, 30 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, 181 reviews
Superhost
Flat in San Gimignano
Tuscan Countryside Hideaway • La Casa Rossa n.3
Business host
18–23 Sept
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
Business host
10–15 Oct
4.99 out of 5 average rating, 85 reviews
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
13–18 Sept
4.99 out of 5 average rating, 138 reviews
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, 141 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
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
Top guest favourite
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
19–24 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
Individual host
18–23 Oct
5.0 out of 5 average rating, 13 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
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 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