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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
14–19 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
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
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
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
"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
Guest favourite
Dome in Volterra
Green Dome @ The Land Before Time Retreats
Business host
20–25 Sept
4.95 out of 5 average rating, 182 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
Flat in Casole d'Elsa
Quintessential tuscan rural apt, big shared pool!
Individual host
6–11 Oct
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Montecastelli Pisano
Exclusive villa with pool jacuzzi wifi and green
Business host
20–27 Mar
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Villa in Montecatini Val di Cecina
Belforti Tower
Business host
15–20 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
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
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 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 Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 47 reviews
Villa in Casole d'Elsa
The Casolare delle Fiabe
Individual host
1–6 Dec