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Search results; Over 1,000 homes in Massa Marittima

Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct, Individual host
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5.0 out of 5 average rating, 33 reviews
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
3–8 Nov
4.96 out of 5 average rating, 26 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Home in Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 47 reviews
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
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
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
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
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
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
19–24 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Follonica
the old stable
Business host
2–7 Jan
5.0 out of 5 average rating, 9 reviews
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
Home in Massa Marittima
Casa di Lorri - 16th century house in the heart of the village
Individual host
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Villa in Radicondoli
Mulino di Anqua: A Tuscan Oasis
Individual host
15–20 Sept
4.93 out of 5 average rating, 14 reviews
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
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
Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
15–20 Oct
4.99 out of 5 average rating, 70 reviews
Flat in Massa Marittima
Casina Blu Chiassarelli
Individual host
1–6 Feb
Guest favourite
Rooms in Massa Marittima
Mother Earth EARTH
Business host
24–29 Oct
5.0 out of 5 average rating, 7 reviews