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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
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
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
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
4–9 Sept
5.0 out of 5 average rating, 38 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
Home in Colle di Val d'Elsa
Casa Emilio
Business host
11–16 Sept
New place to stay
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
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 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
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
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
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 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
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
Flat in San Gimignano
Teruzzi Country House - Apartment La Buvette
Individual host
13–18 Sept
5.0 out of 5 average rating, 5 reviews