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Search results; Over 1,000 homes in San Gimignano

Top guest favourite
Villa in San Gimignano
Fabulous 3Br Villa with 360° Views!
3 bedrooms, 5 beds, 3 bathrooms
3–8 May, Individual host
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4.95 out of 5 average rating, 75 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
2–7 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in San Gimignano
Apartment at ground floor with garden
Business host
9–14 Nov
4.97 out of 5 average rating, 182 reviews
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 San Gimignano
Private Courtyard | 3BR/3BA | Garage
Individual host
2–7 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Farm stay in San Gimignano
Casa Renai - holidays with friends in San Gimignano
Business host
18–23 Oct
5.0 out of 5 average rating, 48 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Home in Volterra
Vacation home with private pool, view
Individual host
5–10 Oct
5.0 out of 5 average rating, 15 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
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
6–11 Sept
New place to stay
Top guest favourite
Farm stay in Lastra a Signa
Farmhouse in Tuscany hills
Business host
18–23 Oct
4.97 out of 5 average rating, 118 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
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
Individual host
13–18 Sept
5.0 out of 5 average rating, 4 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
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
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
Individual host
2–7 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Home in San Gimignano
Casa Margheri
Individual host
1–6 Dec
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Villa in San Gimignano
Exclusive Villa with pool in San Gimignano
Business host
2–7 Sept
4.97 out of 5 average rating, 37 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