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Search results; Over 1,000 homes in Massa Marittima

Cottage in Massa Marittima
Country cottege olive trees garden near seaside
2 bedrooms, 1 bed, 1 private bathroom
23–30 Sept, Individual host
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4.71 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
Individual host
23–28 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
7–12 Sept
4.99 out of 5 average rating, 114 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
18–23 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
31 Oct – 5 Nov
4.96 out of 5 average rating, 26 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
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 Volterra
Vacation home with private pool, view
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
Home in Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
10–15 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
20–25 Sept
New place to stay
Superhost
Holiday home in Scarlino
Glamping Green Sensations "Suite Passion"
Business host
14–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
15–20 Oct
4.99 out of 5 average rating, 69 reviews
Guest favourite
Cottage in Massa Marittima
Frantoio Apartment - Borgo Le Moraiole
Business host
28 Sept – 3 Oct
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 Belvedere
Casa Il Leccio – Relax and nature in Tuscany
Individual host
28 Sept – 3 Oct
5.0 out of 5 average rating, 34 reviews