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Search results; Over 1,000 homes in San Casciano in Val di Pesa
Over 1,000 homes in San Casciano in Val di Pesa
Guest favourite
Guest favourite
Home in San Casciano V.Pesa (FI)
Ambrogetta by Interhome.
4 bedrooms
,
·
3 private bathrooms
3–10 Oct
3–10 Oct
,
·
Business host
£1,939
total
Show price breakdown
£1,939 total
,
·
4.85 out of 5 average rating, 34 reviews
4.85 (34)
Guest favourite
Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
Individual host
19–26 Sept
19–26 Sept
£2,864
£2,504
total
Show price breakdown
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Top guest favourite
Guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
Individual host
3–8 Nov
3–8 Nov
£700
£643
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 89 reviews
5.0 (89)
Top guest favourite
Guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
Individual host
19–24 Sept
19–24 Sept
£1,878
£1,626
total
Show price breakdown
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
Individual host
2–7 Oct
2–7 Oct
£3,703
total
Show price breakdown
£3,703 total
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favourite
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
Individual host
11–16 Oct
11–16 Oct
£1,124
£901
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
Individual host
15–20 Sept
15–20 Sept
£2,996
total
Show price breakdown
£2,996 total
New place to stay
New
Top guest favourite
Guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
Business host
Business host
11–16 Nov
11–16 Nov
£1,117
£871
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 221 reviews
5.0 (221)
Top guest favourite
Guest favourite
Villa in Barberino Tavarnelle
Chianti Holidays, Il Poggetto by Alfina
Individual host
Individual host
20–25 Sept
20–25 Sept
£1,217
£1,095
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
Business host
7–12 Oct
7–12 Oct
£2,393
total
Show price breakdown
£2,393 total
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Superhost
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
Individual host
14–19 Nov
14–19 Nov
£12,686
total
Show price breakdown
£12,686 total
Free cancellation
Top guest favourite
Guest favourite
Farm stay in Barberino Val d'Elsa
Apartment in a farmhouse in Chianti
Business host
Business host
7–12 Oct
7–12 Oct
£1,616
£1,348
total
Show price breakdown
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Guest favourite
Guest favourite
Home in Bagno A Ripoli
Casa Spiano
Business host
Business host
24–29 Sept
24–29 Sept
£2,135
£1,889
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Superhost
Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
Individual host
20–25 Sept
20–25 Sept
£1,646
£1,019
total
Show price breakdown
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
Individual host
31 Oct – 7 Nov
31 Oct – 7 Nov
£3,270
£2,496
total
Show price breakdown
Weekly discount
Free cancellation
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Farm stay in Certaldo
Farmhouse exclusive use Chianti area infinity pool
Business host
Business host
18–23 Oct
18–23 Oct
£2,541
total
Show price breakdown
£2,541 total
Free cancellation
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Top guest favourite
Guest favourite
Flat in Rignano sull'Arno
VIRGO apartment
Business host
Business host
20–25 Sept
20–25 Sept
£1,338
total
Show price breakdown
£1,338 total
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favourite
Guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
Individual host
27 Oct – 1 Nov
27 Oct – 1 Nov
£3,625
£3,189
total
Show price breakdown
Free cancellation
4.99 out of 5 average rating, 114 reviews
4.99 (114)
Superhost
Superhost
Farm stay in San Casciano In Val di Pesa
Tuscan Vacation Home
Individual host
Individual host
1–6 Oct
1–6 Oct
£540
total
Show price breakdown
£540 total
Free cancellation
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