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Search results; Over 1,000 homes in Massa Marittima

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Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
Individual host
3–8 Sept
5.0 out of 5 average rating, 32 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 112 reviews
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Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
Individual host
4–9 Sept
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
31 Oct – 5 Nov
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Apartment in Noce
Historic 17th-century farmhouse in Chianti, Tuscany
Business host
25–30 Oct
5.0 out of 5 average rating, 218 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
5–10 Sept
New place to stay
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Villa in Castagneto Carducci
sea view villa with private infinity pool
Business host
10–17 Oct
4.99 out of 5 average rating, 123 reviews
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Top guest favourite
Apartment in Valpiana
Infinity pool overlooking the woods, sea just minutes away
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
10–15 Sept
4.98 out of 5 average rating, 57 reviews
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Top guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
Business host
9–14 Oct
4.98 out of 5 average rating, 46 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Top guest favourite
Home in Suvereto
The House in the Castle and the Terrace overlooking the Village
Individual host
13–18 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
8–13 Oct
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Volterra
Vacation home with private pool, view
Individual host
5–10 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Bivio di Ravi
The House of Paintings
Business host
22–27 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Rosignano Marittimo
Frontemare house with exclusive sea access
Business host
13–18 Oct
4.95 out of 5 average rating, 107 reviews