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Search results; Over 1,000 homes in San Casciano in Val di Pesa

Top guest favourite
Cottage in San Casciano In Val di Pesa
Chianti Independent barn
2 bedrooms, 3 beds, 2 private bathrooms
23–28 Oct, Business host
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4.84 out of 5 average rating, 177 reviews
Superhost
Villa in San Casciano In Val di Pesa
Villa Casavecchia 26+ people
Individual host
14–19 Nov
Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
19–26 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Villa in Impruneta
Exclusive Estate: Concierge service & heated pool
Individual host
4–9 Oct
4.99 out of 5 average rating, 145 reviews
Guest favourite
Flat in San Casciano In Val di Pesa
Chianti Prestige Apartment • Terrazza & Relax
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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 Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 reviews
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
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
19–24 Sept
5.0 out of 5 average rating, 12 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in San Casciano In Val di Pesa
Authentic Tuscan home: history, wine and relax
Individual host
20–25 Oct
5.0 out of 5 average rating, 45 reviews
Guest favourite
Villa in Le Quattro Strade
Villa Quattro Strade in Chianti
Individual host
7–12 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Room in San Casciano In Val di Pesa
Independent loft in the heart of Chianti
Individual host
4–9 Oct
5.0 out of 5 average rating, 64 reviews
Superhost
Farm stay in San Casciano In Val di Pesa
Tuscan Vacation Home
Individual host
1–6 Oct
Flat in San Casciano In Val di Pesa
Cottage in Chianti
Business host
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in San Casciano In Val di Pesa
“ Giorgio” Tuscan barn
Individual host
24–29 Sept
5.0 out of 5 average rating, 7 reviews