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Search results; Over 1,000 homes in Castiglioni

Guest favourite
Apartment in Castiglioni
[Old House With Pool In The Tuscan Hills]
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct, Individual host
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4.93 out of 5 average rating, 56 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
6–11 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
Individual host
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Holiday home in Colle di Val d'Elsa
Behind the Walls
Individual host
27 Sept – 2 Oct
4.91 out of 5 average rating, 35 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Flat in Colle di Val d'Elsa
CASTELLo - Home Sweet Home Tuscany
Individual host
5–10 Sept
4.97 out of 5 average rating, 31 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
18–23 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
4–9 Sept
5.0 out of 5 average rating, 38 reviews
Home in Colle di Val d'Elsa
Casa Emilio
Business host
6–11 Sept
New place to stay
Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
4–9 Sept
5.0 out of 5 average rating, 3 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
Guest favourite
Villa in San Gimignano
Villa with breathtaking views of the towers of San Gimignano
Business host
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Apartment in Noce
Historic 17th-century farm in Chianti, Tuscany
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 218 reviews
Top guest favourite
Flat in San Gimignano
Papavero Rosso Holiday Home
Individual host
7–12 Oct
5.0 out of 5 average rating, 23 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
Apartment in San Gimignano
Relax in San Gimigano: Terrace + free Parking.
Individual host
21–26 Oct
4.89 out of 5 average rating, 89 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
Business host
16–21 Oct
5.0 out of 5 average rating, 32 reviews
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
Individual host
13–18 Sept
5.0 out of 5 average rating, 5 reviews