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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
15–20 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Casole d'Elsa
Casa Panorama
Individual host
18–23 Oct
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Flat in Casole d'Elsa
Holiday House "Anna" - the MUSICIAN for 4-5 persons
Business host
6–11 Nov
5.0 out of 5 average rating, 37 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
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
Apartment in Casole d'Elsa
Rondini apartment with pool in farmhouse
Business host
11–16 Oct
4.91 out of 5 average rating, 57 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
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
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
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
30 Sept – 5 Oct
4.95 out of 5 average rating, 183 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Top guest favourite
Apartment in Noce
Historic 17th-century villa in Chianti, Tuscany
Business host
11–16 Nov
5.0 out of 5 average rating, 222 reviews
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
16–21 Sept
4.99 out of 5 average rating, 138 reviews
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
Individual host
6–11 Oct
4.98 out of 5 average rating, 218 reviews
Home in CASOLE D'ELSA
Casa Lucciana - Tuscan Holiday
Individual host
16–21 Sept
5.0 out of 5 average rating, 4 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
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews