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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
7–12 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
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
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
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
Flat in Follonica
the old stable
Business host
2–7 Jan
5.0 out of 5 average rating, 9 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
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
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
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
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
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Guest favourite
Holiday home in Scarlino
Glamping Green Sensations "Suite Diamond"
Business host
25–30 Sept
5.0 out of 5 average rating, 18 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
20–25 Sept
New place to stay
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
Flat in Radicondoli
Tuscan Hilltop Retreat | Views, Charm, Fireplace
3 bedrooms, 3 beds, 3 bathrooms
21–26 Sept
4.98 out of 5 average rating, 49 reviews