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Search results; Over 1,000 homes in San Donato

Top guest favourite
Villa in San Donato
Casa Colombaia, in the Chiantishire
4 bedrooms, 5 beds, 3 private bathrooms
24–29 Sept, Individual host
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4.96 out of 5 average rating, 96 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in San Donato
Loft in the heart of Chianti.
Individual host
14–19 Oct
4.97 out of 5 average rating, 117 reviews
Top guest favourite
Flat in San Donato
My home
Individual host
23–28 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Barberino Val d'Elsa
Apartment in Chianti at Mulino dell'Argenna
Individual host
17–22 Oct
4.99 out of 5 average rating, 151 reviews
Guest favourite
Room in San Donato
Palazzo Malaspina, King Room with Jacuzzi
Individual host
21–26 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 89 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
17–22 Sept
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
Villa in Madonna di Pietracupa
Villa sonia - luxury villa rental in madonna di pi
Business host
19–26 Sept
5.0 out of 5 average rating, 3 reviews
Home in San Donato
Holiday House Casa Beccaccia Private Pool
Individual host
1–8 Nov
Top guest favourite
Flat in Barberino Tavarnelle
Podere Le Casette Garden
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
16–21 Oct
4.98 out of 5 average rating, 47 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay