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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
24–29 Oct
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
3–8 Nov
4.96 out of 5 average rating, 26 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
19–24 Sept
4.98 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Volterra
Vacation home with private pool, view
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 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, 52 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
23–28 Oct
4.98 out of 5 average rating, 48 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
27 Oct – 1 Nov
4.99 out of 5 average rating, 114 reviews
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Top guest favourite
Home in Monteverdi Marittimo
Villa with swimming pool in the oasis of Acquaferrata
Business host
30 Sept – 5 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Apartment in Montieri
Cupiano Farm "Querciolettaia/Legnaio"
Business host
28 Sept – 3 Oct
4.96 out of 5 average rating, 56 reviews
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Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Flat in Follonica
the old stable
Business host
2–7 Jan
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews