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Search results; Over 1,000 homes in Montescudaio

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Top guest favourite
Flat in Montescudaio
Elegant and bright apartment in Montescudaio
1 bedroom, 1 bed, 1 private bathroom
9–14 Sept, Individual host
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4.93 out of 5 average rating, 179 reviews
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Superhost
Home in Montescudaio
Open space surrounded by nature
Individual host
24–29 Oct
4.96 out of 5 average rating, 135 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
Casina del Fabbro | Sea & Hill Views, Village
Individual host
10–17 Oct
4.86 out of 5 average rating, 7 reviews
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Superhost
Flat in Montescudaio
Residenza Le Mura
Individual host
1–6 Sept
5.0 out of 5 average rating, 30 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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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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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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Superhost
Home in Montescudaio
Podere La Quercia - Tuscan farmhouse
Individual host
1–6 Oct
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Flat in Montescudaio
Mimosa • Tuscan oasis with swimming pool
Business host
11–16 Oct
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Superhost
Farm stay in Montescudaio
Countryside apartment in villa close to the beach
Business host
4–11 Oct
4.72 out of 5 average rating, 90 reviews
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Guest favourite
Flat in Casale Marittimo
In the Tuscan countryside, Podere I Luoghi with swimming pool Ap3
Business host
4–9 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Chianni
The Cottage to relax and enjoy
Individual host
10–15 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Flat in Guardistallo
Ai Massi Maestrale Farmhouse (42 sqm two-room apartment)
Business host
5–10 Oct
4.9 out of 5 average rating, 10 reviews
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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
Home in Montescudaio
Casa Elisabetta on the hills of Montescudaio (Pi)
Individual host
1–6 May
5.0 out of 5 average rating, 5 reviews
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Home in Lajatico
Casa Gloria: Private Pool & Stunning Tuscan Views
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Montaione
Cercis - La Palmierina
Individual host
24–29 Oct
4.96 out of 5 average rating, 143 reviews