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Search results; Over 1,000 homes in Montescudaio

Guest favourite
Flat in Montescudaio
IL PICCINO 29, Romantic Experience in the Hamlet....
1 bedroom, 1 bed, 1 private bathroom
25–30 Jul
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4.94 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Montescudaio
Elegant and bright apartment in Montescudaio
4.94 out of 5 average rating, 172 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Sept
Apartment in Montescudaio
Casa Angiolina
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
Home in Montescudaio
PERO Cottage by Interhome
1 bedroom, 2 beds, 1 bathroom
3–8 Jul
Home in Riparbella
Tuscan Villa, Infinity Pool, Sea Views, New 2026
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Guest favourite
Home in Guardistallo
Il Pietraio
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Home in Casale Marittimo
Countryside-panoramic sea Casale Marittimo Tuscany
5.0 out of 5 average rating, 62 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Sept – 5 Oct
Top guest favourite
Home in Riparbella
Nocolino25, Entire Eco-Villa
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 7 beds, 3 bathrooms
28 May – 2 Jun
Flat in Guardistallo
Ai Massi Libeccio Farmhouse (three-room apartment 65sqm)
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Suvereto
The House in the Castle and the Terrace overlooking the Village
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
4–9 Sept
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
Superhost
Flat in Casale Marittimo
In the Tuscan countryside, Podere I Luoghi with swimming pool Ap3
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 3 bathrooms
10–15 Sept
Home in Montescudaio
Casa Elisabetta on the hills of Montescudaio (Pi)
4 bedrooms, 4 beds, 1.5 bathrooms
1–6 May
Top guest favourite
Flat in Ponteginori
Tuscany - Il Catrino II Farmhouse
5.0 out of 5 average rating, 23 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–11 Sept
Top guest favourite
Flat in Collesalvetti
"Il Magnifico" Medici apartment
4.98 out of 5 average rating, 90 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Farm stay in Terricciola
Two Bedroom apartment @Agriturismo Vallorsi
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 1 bed, 1 bathroom
19–24 Sept
Top guest favourite
Apartment in Fabbrica
Family Tuscany House
4.97 out of 5 average rating, 69 reviews, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Villa in Castagneto Carducci
sea view villa with private infinity pool
4.99 out of 5 average rating, 119 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–19 Sept