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Search results; Over 1,000 homes in Massa Marittima

Top guest favourite
Apartment in Massa Marittima
Panoramic view 10 minutes from Massa Marittima and the sea
2 bedrooms, 2 beds, 1 private bathroom
24–29 Oct
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4.98 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Massa Marittima
Il Bell'Arco
2 bedrooms, 3 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Farm stay in Montebamboli
TerraMadre ANIMA
2 bedrooms, 2 beds, 1 bathroom
3–8 Nov
4.96 out of 5 average rating, 26 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Apartment in Montieri
Cupiano Farm "Querciolettaia/Legnaio"
2 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Monticiano
Typical Tuscan Cottage with swimming pool and park
3 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Apartment in Valpiana
Infinity Pool in the green agritourism with a view of the woods
2 bedrooms, 3 beds, 1 bathroom
23–28 Oct
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Farm stay in Radicondoli
The pomegranate, Podere il Giglio
2 bedrooms, 2 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Monteverdi Marittimo
Villa with a swimming pool in the oasis of Acquaferrata
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Valpiana
Infinity pool overlooking the woods, sea just minutes away
1 bedroom, 1 double bed, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 52 reviews
Guest favourite
Holiday home in Scarlino
Glamping Green Sensations "Suite Diamond"
2 bedrooms, 2 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Villa in Montecastelli Pisano
Exclusive villa with pool jacuzzi wifi and green
2 bedrooms, 3 beds, 2 bathrooms
20–27 Mar
4.96 out of 5 average rating, 53 reviews
Home in Massa Marittima
Casa di Lorri - 16th century house in the heart of the village
2 bedrooms, 2 double beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Belvedere
Casa Il Leccio – Relax and nature in Tuscany
2 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Follonica
the old stable
2 bedrooms, 4 beds, 1 bathroom
2–7 Jan
5.0 out of 5 average rating, 9 reviews
Holiday home in Canneto
House in Borgo Toscano with a View, Garden, and BBQ
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept