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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
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4.77 out of 5 average rating, 117 reviews
Top guest favourite
Home in San Gimignano
"Vernaccia" by Podere la Fonte
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Villa in Volterra
Luxury Villa + Annex with Jacuzzi + Pool, Chef
6 bedrooms, 8 beds, 6 bathrooms
11–17 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Flat in San Gimignano
Four-room villa (3 bedrooms and kitchen)
3 bedrooms, 5 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Flat in San Gimignano
Tuscan Countryside Hideaway • La Casa Rossa n.3
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
Luxe
Villa in Volterra
Velari
3 bedrooms, 3 beds, 4 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Villa in San Gimignano
Fabulous 3Br Villa with 360° Views!
3 bedrooms, 5 beds, 3 bathrooms
3–8 May
4.95 out of 5 average rating, 74 reviews
Top guest favourite
Home in Simignano
Casa al Gianni - The Simignano Barn
5 bedrooms, 5 beds, 4 bathrooms
13–18 Sept
4.98 out of 5 average rating, 185 reviews
Top guest favourite
Holiday home in Lajatico
Rosa: Tuscan Views & Pool, Walk to Town
1 bedroom, 3 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 38 reviews
Superhost
Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 double beds, 6 bathrooms
2–7 Aug
Top guest favourite
Home in Volterra
Charming Tuscan Villa with pool
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
22–27 Aug
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Villa in Impruneta
The Tower
2 bedrooms, 3 beds, 2 bathrooms
6–11 Nov
5.0 out of 5 average rating, 183 reviews
Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
4.98 out of 5 average rating, 332 reviews
Top guest favourite
Villa in Impruneta
Luxury Estate | Heated Pool & Private Concierge
6 bedrooms, 6 beds, 7 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
4 bedrooms, 6 beds, 3 bathrooms
19–24 Sept
4.98 out of 5 average rating, 56 reviews
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
1 double bed, 1 bathroom
13–18 Aug
4.97 out of 5 average rating, 138 reviews