A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

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 CA $888
CA $1,032 total
includes taxes & fees
Jul 7 - Jul 8
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $175
CA $200 total
includes taxes & fees
Aug 1 - Aug 2
Casa Vacanze Le Case
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $222
CA $315 total
includes taxes & fees
Jul 5 - Jul 6
Chianti Craft House Badia a Passignano
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 CA $189
CA $194 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Home 'La Casa Gialla Di Buonconvento' with Wi-Fi and Air Conditioning
Outdoor dining

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Arezzo
The price is CA $124
CA $173 total
includes taxes & fees
Jul 5 - Jul 6
Dolce Casa 2 by Tiny Away
1 bedroom, WiFi, bed sheets

Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Arrezo
The price is CA $134
CA $183 total
includes taxes & fees
Jul 5 - Jul 6
Dolce Casa 1 by Tiny Away
Spa

Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $156
CA $279 total
includes taxes & fees
Jul 8 - Jul 9
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
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 CA $144
CA $257 total
includes taxes & fees
Jul 7 - Jul 8
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Outdoor dining

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveller
The price is CA $205
CA $289 total
includes taxes & fees
Jul 12 - Jul 13
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
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 CA $133
CA $399 total
includes taxes & fees
Jul 5 - Jul 6
House with views of the Chianti
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 CA $124
CA $131 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Outdoor dining

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $349
CA $437 total
includes taxes & fees
Jul 5 - Jul 6
Casa Marisa in Castellina in Chianti
1 bedroom, in-room safe, desk, iron/ironing board

The Wishing Well - The Wishing Well

The Wishing Well - The Wishing Well
Firenze
9.2 out of 10, Wonderful, (5 reviews)
"House was very clean and close enough to the city without the noise or traffic. Host is lovely and responds promptly. Definitely would book again."
Canada
Grace M.
The price is CA $232
CA $366 total
includes taxes & fees
Aug 1 - Aug 2
The Wishing Well - The Wishing Well
Property grounds

country house with garden ,pool,children's play area ,Tuscany,15 from Florence

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (82 reviews)
"The hostess Sonia was fabulous."
United States
Kim
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
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 CA $102
CA $183 total
includes taxes & fees
Jul 10 - Jul 11
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is CA $437
CA $591 total
includes taxes & fees
Jul 8 - Jul 9
Charming Siena Countryside Stay
Outdoor dining

Casa Crevole di Martina in the Heart of Tuscany

Casa Crevole di Martina in the Heart of Tuscany
Murlo
10.0 out of 10, Exceptional, (1 review)
"Nach einer herzlichen Begrüßung durch die Gastgeberin haben wir ein paar entspannte Tage verbracht. Im Kühlschrank befanden sich für uns schon einmal keiner Erfrischungen. Obwohl wir nur 4 Nächte blieben, gab es einen Handtuchtausch nach 2 Tagen. Total überrascht hat uns aber der selbstgebackene Kuchen der für uns bereit stand. Wir würden hier jeder Zeit wieder Urlaub machen und können die Unterkunft mehr wir nur empehlen."
Germany
Sybille F.
The price is CA $391
CA $430 total
includes taxes & fees
Jul 5 - Jul 6
Casa Crevole di Martina in the Heart of Tuscany
Interior

Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is CA $171
CA $213 total
includes taxes & fees
Jul 4 - Jul 5
Holiday Home 'La Casina All'angolo'
Terrace/patio

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort

Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Antria
The price is CA $218
CA $259 total
includes taxes & fees
Jul 7 - Jul 8
Charming bungalow with whirlpool in Tuscany: peace, nature and comfort
Dining

Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is CA $291
CA $453 total
includes taxes & fees
Jul 15 - Jul 16
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
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.
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Top Gaiole in Chianti Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"This is a traditional and historic building with high ceilings and a beautiful garden overlooking the surrounding countryside.It is not a modern contemporary hotel, but the rooms are lovely, the garden was beautiful and a good breakfast too. There is a small bar in the evening, but no restaurant for an evening meal, but frankly you will likely want to explore and eat out at one of the many restaurants in the old town. A great find."
David 4-night trip
Posted 11 hours ago
Palazzo Ravizza

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
116
Accommodation
1574 Vacation Homes
Lowest Price
CA $131
Highest Price
CA $1,032