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Search results; Over 1,000 homes in Montegabbro

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Top guest favourite
Villa in Volterra
Luxury A/C Villa + Annex with Jacuzzi + Pool, Chef
6 bedrooms, 8 beds, 6 bathrooms
11–17 Oct
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Castle in Poggibonsi
Castello Di Badia – Panoramic Pool Overlooking Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 72 reviews
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Guest favourite
Flat in Colle di Val d'Elsa
Charming farmhouse "LA PIEVE - Duke Suite
1 bedroom, 4 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 48 reviews
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Guest favourite
Flat in San Gimignano
Four-room villa (3 bedrooms and kitchen)
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Villa in San Gimignano
Exclusive Villa with pool in San Gimignano
10 bedrooms, 11 beds, 6.5 bathrooms
9–14 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds, 2.5 bathrooms
6–11 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Luxe
Villa in Volterra
Velari
3 bedrooms, 3 beds, 4 bathrooms
9–14 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
1 double bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 189 reviews
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Home in CASOLE D'ELSA
Casa Lucciana - Tuscan Holiday
2 bedrooms, 4 beds, 1.5 bathrooms
9–14 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Poggibonsi
Laura Chianti Holidays
2 bedrooms, 5 beds, 2 bathrooms
22–27 Nov
4.98 out of 5 average rating, 343 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 390 reviews
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Top guest favourite
Farm stay in San Gimignano
Casa Renai - holidays with friends in San Gimignano
13 bedrooms, 15 beds, 9 bathrooms
18–23 Oct
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Flat in San Gimignano
Apartment at ground floor with garden
2 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.97 out of 5 average rating, 184 reviews
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Villa in Radicondoli
Villa Le Bolli, a holiday to be loved
12 bedrooms, 21 beds, 13 bathrooms
2–7 Nov
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews