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Search results; Over 1,000 homes in Massa Marittima

Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
Individual host
23–28 Oct
5.0 out of 5 average rating, 32 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
2–7 Sept
5.0 out of 5 average rating, 4 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
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
6–11 Sept
4.99 out of 5 average rating, 113 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 Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 84 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
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 Volterra
Vacation home with private pool, view
Individual host
5–10 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
2–7 Sept
4.98 out of 5 average rating, 60 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 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
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
Home in Colle di Val d'Elsa
Casa Emilio
Business host
6–11 Sept
New place to stay
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
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
2–7 Sept
New place to stay
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, 47 reviews
Guest favourite
Farm stay in Montaione
Tenuta Collerucci | Villa with private pool
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 6 reviews