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Search results; Over 1,000 homes in Casole d'Elsa

Guest favourite
Cottage in Casole d'Elsa
Whispering cypresses cottage. Stunning pool view.
2 bedrooms, 3 beds, 1 private bathroom
3–8 Oct, Business host
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4.92 out of 5 average rating, 36 reviews
Guest favourite
Apartment in Casole d'Elsa
Dimora San Donato - Apt.1985
Individual host
13–18 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Casole d'Elsa
Casa Panorama
Individual host
8–13 Oct
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Apartment in Casole d'Elsa
Rondini apartment with pool in farmhouse
Business host
9–14 Oct
4.91 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Casole d'Elsa
Mirella apartment in the historic center
Individual host
19–24 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Casole d'Elsa
Holiday House "Anna" - the MUSICIAN for 4-5 persons
Business host
14–19 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Casole d'Elsa
"Anna" holiday home - the POET for 4 people
Business host
4–9 Oct
5.0 out of 5 average rating, 17 reviews
Luxe
Villa in Casole d'Elsa
Villa Sublimis by Villas in Med
Business host
19–24 Sept
5.0 out of 5 average rating, 10 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
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
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
Farm stay in Poggibonsi
I Melograni del Chianti - Focolare Apartment
Business host
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Farm stay in Radicondoli
The cherry tree, Podere il giglio
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Villa in Volterra
Luxury A/C Villa + Annex with Jacuzzi + Pool, Chef
Business host
11–17 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
19–24 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
13–18 Sept
4.99 out of 5 average rating, 138 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
19–24 Oct
4.98 out of 5 average rating, 218 reviews
Top guest favourite
Home in Volterra
Vacation home with private pool, view
Individual host
31 Oct – 5 Nov
5.0 out of 5 average rating, 15 reviews