View over the hills from the Brolio Castle

Search Vacation Homes in Gaiole in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Gaiole in Chianti vacation homes

Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is ￥101,961
￥118,565 total
includes taxes & fees
Jun 21 - Jun 22
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Outdoor pool

House with pool for 4 pax

House with pool for 4 pax
Casole d'Elsa
9.4 out of 10, Exceptional, (3 reviews)
"Besser kann man es nicht haben. Den Pool hatten wir gefühlt immer für uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen Sehenswürdigkeiten in der Region waren schnell zu erreichen. In der Unterkunft war es sehr ruhig, ideal um sich zu erholen. Traumhaft schön. Wir kommen gerne wieder. Ciao Oli"
Germany
Oliver E.
The price is ￥34,418
￥60,244 total
includes taxes & fees
Jun 18 - Jun 19
House with pool for 4 pax
Outdoor dining

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is ￥10,033
￥19,322 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Exterior

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is ￥14,919
￥27,924 total
includes taxes & fees
Jun 18 - Jun 19
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is ￥17,907
￥20,627 total
includes taxes & fees
Jun 22 - Jun 23
Casa Vacanze Le Case
Outdoor dining

Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is ￥15,978
￥20,808 total
includes taxes & fees
Jun 26 - Jun 27
Peaceful corner with garden between Chianti and Crete, very close to Old Town
Interior

Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥18,133
￥22,964 total
includes taxes & fees
Jun 19 - Jun 20
Holiday Home 'La Casina All'angolo'
Exterior detail

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is ￥14,274
￥15,017 total
includes taxes & fees
Jun 18 - Jun 19
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Spa

Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is ￥19,113
￥33,457 total
includes taxes & fees
Jun 22 - Jun 23
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
1 bedroom, WiFi, bed sheets

Little cozy house

Little cozy house
Loro Ciuffenna
The price is ￥13,005
￥16,349 total
includes taxes & fees
Jun 18 - Jun 19
Little cozy house
Smart TV

House with separate entrance at the gates of Florence and Chianti

House with separate entrance at the gates of Florence and Chianti
Impruneta
The price is ￥21,738
￥35,487 total
includes taxes & fees
Jun 19 - Jun 20
House with separate entrance at the gates of Florence and Chianti
Interior

THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is ￥22,295
￥28,280 total
includes taxes & fees
Jun 18 - Jun 19
THE CASINA OF SANT 'AGOSTINO
Outdoor dining

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is ￥15,275
￥45,826 total
includes taxes & fees
Jul 5 - Jul 6
House with views of the Chianti
Property grounds

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (79 reviews)
"Very quiet and nice place to stay. Host’s were great and easy to communicate with"
United States
Tanya G.
The price is ￥22,354
￥25,707 total
includes taxes & fees
Jun 23 - Jun 24
Villa with large garden in the Chianti hills
Exterior detail

GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
Siena
The price is ￥16,822
￥33,377 total
includes taxes & fees
Jun 23 - Jun 24
GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
Exterior

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning

Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Buonconvento
The price is ￥24,110
￥24,667 total
includes taxes & fees
Jun 25 - Jun 26
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Property grounds

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
8.0 out of 10, Very Good, (1 review)
"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is ￥20,066
￥37,345 total
includes taxes & fees
Jun 22 - Jun 23
Romantic farm in the Sienese hills
Property grounds

Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com

Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com
San Gersolé-torre Rosse
The price is ￥31,416
￥65,028 total
includes taxes & fees
Jun 20 - Jun 21
Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com
Exterior

Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is ￥735,737
￥735,737 total
includes taxes & fees
Jun 26 - Jun 27
Ebbio – Villa and Organic Farm in Monteriggioni
Pool

Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com

Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com
Impruneta
The price is ￥39,524
￥73,946 total
includes taxes & fees
Jun 20 - Jun 21
Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Great location, spacious room, lovely bathroom, full breakfast included and super helpful staff."
Amy 2-night trip
Posted 15 hours ago
Hotel Chiusarelli

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
8
Accommodation
1498 Vacation Homes
Lowest Price
￥20,627
Highest Price
￥20,627