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Search results; Over 1,000 homes in Massa Marittima

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Tent in Massa Marittima
Le Sedici Wine Glamping
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
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Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
2 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
2 bedrooms, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.96 out of 5 average rating, 26 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Flat in Follonica
the old stable
2 bedrooms, 4 beds, 1 bathroom
24–29 Dec
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Bivio di Ravi
The House of Paintings
2 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Suvereto
The House in the Castle and the Terrace overlooking the Village
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Oct
5.0 out of 5 average rating, 18 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
New place to stay
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Superhost
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
1 bedroom, 2 beds, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 109 reviews
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Top guest favourite
Apartment in Valpiana
Infinity pool overlooking the woods, sea just minutes away
1 bedroom, 1 double bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
2 bedrooms, 3 beds, 1 bathroom
9–14 Oct
4.98 out of 5 average rating, 46 reviews
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Top guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms, 2 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Villa in Montecastelli Pisano
Exclusive villa with pool jacuzzi wifi and green
2 bedrooms, 3 beds, 2 bathrooms
20–27 Mar
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds, 3.5 bathrooms
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Top guest favourite
Villa in Castagneto Carducci
sea view villa with private infinity pool
3 bedrooms, 5 beds, 2 bathrooms
10–17 Oct
4.99 out of 5 average rating, 123 reviews
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Top guest favourite
Apartment in Montieri
Cupiano Farm "Querciolettaia/Legnaio"
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
4.96 out of 5 average rating, 55 reviews
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Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay