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Search results; Over 1,000 homes in Massa Marittima

Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct, Individual host
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5.0 out of 5 average rating, 33 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 Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 47 reviews
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
Business host
3–8 Nov
4.96 out of 5 average rating, 26 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
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 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 Volterra
La Paiolina: pool, jacuzzi & sauna
Individual host
19–24 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
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, 52 reviews
Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
Business host
1–6 May
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
15–20 Oct
4.99 out of 5 average rating, 70 reviews
Guest favourite
Villa in Radicondoli
Mulino di Anqua: A Tuscan Oasis
Individual host
16–21 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
19–24 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 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, 6 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, 7 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