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Search results; Over 1,000 homes in San Gimignano

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Top guest favourite
Home in San Gimignano
La Moraiola - Characteristic Tuscan barn
2 bedrooms, 4 beds, 2 private bathrooms
1–6 Sept
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4.99 out of 5 average rating, 68 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Apartment in San Gimignano
Casaglia Residence
2 bedrooms, 4 beds
5–10 Oct
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Holiday home in San Gimignano
Breathe in Tuscany: 180° view of the hills
2 bedrooms, 3 beds
9–14 Sept
4.98 out of 5 average rating, 162 reviews
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Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds
1–6 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Apartment in San Gimignano
"HOME SWEET HOME" appartamento a San Gimignano
1 bedroom, 2 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 53 reviews
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Flat in San Gimignano
Apartment at ground floor with garden
2 bedrooms, 4 beds
9–14 Nov
4.97 out of 5 average rating, 181 reviews
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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, 97 reviews
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Farm stay in Lastra a Signa
Farmhouse in Tuscany hills
2 bedrooms, 3 beds
18–23 Oct
4.97 out of 5 average rating, 118 reviews
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Superhost
Flat in San Gimignano
Tuscan Countryside Hideaway • La Casa Rossa n.3
2 bedrooms, 2 beds
18–23 Sept
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Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds
6–11 Sept
4.99 out of 5 average rating, 113 reviews
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Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in San Gimignano
Casa Margheri
2 bedrooms, 2 beds
1–6 Dec
4.99 out of 5 average rating, 88 reviews
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Flat in San Gimignano
Teruzzi Country House - Apartment Il Caminetto
2 bedrooms, 3 beds
1–6 Sept
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Flat in San Gimignano
Cantina Suite
2 bedrooms, 1 king bed
14–19 Sept
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Top guest favourite
Apartment in Gambassi Terme
Cosy Tuscan Home near Florence & San Gimignano
1 bedroom, 2 beds
16–21 Oct
4.99 out of 5 average rating, 127 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
15–20 Sept
New place to stay
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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
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Flat in Colle di Val d'Elsa
Charming farmhouse "LA PIEVE - Duke Suite
1 bedroom, 4 beds
24–29 Sept
4.98 out of 5 average rating, 48 reviews