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Search results; Over 1,000 homes in San Gimignano

Guest favourite
Holiday home in San Gimignano
Tuscan House with Private Jacuzzi in Chianti
2 bedrooms, 2 beds, 2 private bathrooms
7–12 Jan
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4.95 out of 5 average rating, 95 reviews
Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in San Gimignano
AnticaVista, Luxury Apartment with Tower Views
1 bedroom, 1 double bed
1–6 Nov
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Farm stay in Lastra a Signa
Farmhouse in Tuscany hills
2 bedrooms, 3 beds
18–23 Oct
4.97 out of 5 average rating, 119 reviews
Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
3 bedrooms, 3 double beds
12–17 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in San Gimignano
Apartment at ground floor with garden
2 bedrooms, 4 beds
9–14 Nov
4.97 out of 5 average rating, 183 reviews
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds
18–23 Oct
5.0 out of 5 average rating, 14 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
15–20 Sept
New place to stay
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds
16–21 Oct
4.98 out of 5 average rating, 47 reviews
Superhost
Flat in San Gimignano
Tuscan Countryside Hideaway • La Casa Rossa n.3
2 bedrooms, 2 beds
18–23 Sept
Guest favourite
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds
2–7 Nov
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Farm stay in San Gimignano
Casa Renai - holidays with friends in San Gimignano
13 bedrooms, 15 beds
18–23 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Volterra
Vacation home with private pool, view
2 bedrooms, 3 beds
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Villa in Il Pino
Exclusive villa private pool florentine farmland
6 bedrooms, 9 beds
4–9 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Villa in San Gimignano
Exclusive Villa with pool in San Gimignano
10 bedrooms, 11 beds
14–19 Sept
4.97 out of 5 average rating, 37 reviews