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Search results; Over 1,000 homes in Massa Marittima

Guest favourite
Loft in Massa Marittima
Authentic Cave House in the heart of the Village!
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept, Individual host
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4.88 out of 5 average rating, 210 reviews
Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
Individual host
24–29 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
9–14 Sept
4.99 out of 5 average rating, 114 reviews
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
31 Oct – 5 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
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
Business host
26–31 Oct
5.0 out of 5 average rating, 32 reviews
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
Top guest favourite
Home in Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 46 reviews
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
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
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
Top guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
Business host
17–22 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
Individual host
26–31 Mar
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
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
Top guest favourite
Home in Ponteginori
Tenuta Tegolaia
Individual host
23–28 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Bivio di Ravi
The House of Paintings
Business host
22–27 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Holiday home in Sovicille
Podere La Castellina - No. 4 FICO
Business host
17–22 Oct
4.96 out of 5 average rating, 109 reviews
Superhost
Holiday home in Scarlino
Glamping Green Sensations "Suite Passion"
Business host
14–20 Sept
5.0 out of 5 average rating, 3 reviews