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Search results; Over 1,000 homes in Montegabbro

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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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Top guest favourite
Townhouse in Quartaia
Casa Lida [Garden+Parking]
2 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 85 reviews
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Top guest favourite
Farm stay in Colle di Val d'Elsa
Farmhouse in the Tuscan countryside
3 bedrooms, 4 beds, 2 bathrooms
1–7 Apr
4.95 out of 5 average rating, 43 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, 190 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
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
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, 7 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
Home in Colle di Val d'Elsa
The House in the Alley – Colle di Val d'Elsa
2 bedrooms, 3 beds, 1 bathroom
5–10 Nov
4.99 out of 5 average rating, 135 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 Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
8 bedrooms, 16 beds, 11.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Tower in San Donato
Luxury apartment in an 1100s tower
1 bedroom, 3 beds, 1 bathroom
20–25 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, 4 reviews
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Room in San Gimignano
Two-room apartment in a villa (1 bedroom and kitchen)
1 single bed, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 11 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, 1 bathroom
17–22 Oct
4.98 out of 5 average rating, 166 reviews