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Search results; Over 1,000 homes in Montescudaio

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Superhost
Farm stay in Montescudaio
Countryside apartment in villa close to the beach
1 bedroom, 2 beds, 1 private bathroom
4–11 Oct, Business host
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4.73 out of 5 average rating, 91 reviews
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Superhost
Home in Montescudaio
Open space surrounded by nature
Individual host
15–20 Oct
4.96 out of 5 average rating, 135 reviews
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Top guest favourite
Flat in Montescudaio
Elegant and bright apartment in Montescudaio
Individual host
9–14 Sept
4.93 out of 5 average rating, 179 reviews
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Home in Montescudaio
Podere Dolce Sonno - Tuscan farmhouse
Individual host
1–8 Sept
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Flat in Montescudaio
Mimosa • Tuscan oasis with swimming pool
Business host
11–16 Oct
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Superhost
Home in Montescudaio
Podere La Quercia - Tuscan farmhouse
Individual host
1–6 Oct
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Flat in Montescudaio
IL PICCINO 29, Romantic Experience in the Hamlet....
Individual host
1–6 Oct
4.96 out of 5 average rating, 23 reviews
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Guest favourite
Home in Montescudaio
Casa Elisabetta on the hills of Montescudaio (Pi)
Individual host
1–6 May
5.0 out of 5 average rating, 6 reviews
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Villa in Montescudaio
Private Villa Acquaviva in Montescudaio/pool
Business host
3–8 Oct
4.67 out of 5 average rating, 21 reviews
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Superhost
Flat in Montescudaio
Residenza Le Mura
Individual host
13–18 Sept
5.0 out of 5 average rating, 31 reviews
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Home in Montescudaio
PERO Cottage by Interhome
Business host
8–13 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Montescudaio
Girasole by Interhome
Business host
25–30 Sept
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Home in Montescudaio
Podere Sant'Angelo - Tuscan Countryside House
Individual host
1–6 Sept
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Top guest favourite
Home in Guardistallo
Da 7 Cervelli
Individual host
15–20 Sept
4.95 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Ponteginori
Tenuta Tegolaia
Individual host
12–17 Sept
5.0 out of 5 average rating, 28 reviews
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Flat in Montecatini Val di Cecina
Le Colmate by Interhome
Business host
31 Oct – 5 Nov
4.8 out of 5 average rating, 30 reviews
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Flat in Montescudaio
Pozzo 2 and 3 Holidays in the "Tuscan" countryside
Individual host
1–6 Sept
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Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
Individual host
4–9 Sept
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Holiday home in Chianni
Elegant Apartment with Pool & Sauna - Tuscan Hills
Business host
27 Oct – 1 Nov
4.9 out of 5 average rating, 39 reviews