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Search results; Over 1,000 homes in Massa Marittima

Superhost
Apartment in Massa Marittima
Penthouse with Private Sauna in Massa Marittima
1 bedroom, 2 beds, 1 private bathroom
4–9 Sept, Business host
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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
18–23 Sept
5.0 out of 5 average rating, 4 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
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
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
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
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
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
6–11 Sept
New place to stay
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 Ponteginori
Tenuta Tegolaia
Individual host
23–28 Sept
5.0 out of 5 average rating, 29 reviews
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
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 Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
Individual host
26–31 Mar
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Rosignano Marittimo
Frontemare house with exclusive sea access
Business host
13–18 Oct
4.95 out of 5 average rating, 108 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
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