Search Vacation Homes in Gaiole in Chianti

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Vacation Homes in Gaiole in Chianti

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

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

Gaiole in Chianti
The price is AED 2,190
AED 2,572 total
includes taxes & fees
7 Jan - 8 January 2026
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Fridge, oven, stovetop, dishwasher
Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi

Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi

Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione Ăš. La dolcezza della proprietaria"
Italy
Anonymous traveler
The price is AED 338
AED 485 total
includes taxes & fees
9 Dec - 10 Dec
Holiday Home 'Piccolo Angolo Di TranquillitĂ ' with Private Garden and Wi-Fi
Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Outdoor pool
Casa Vacanze Le Case

Casa Vacanze Le Case

San Gimignano
9.0 out of 10, Wonderful, (8)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 394
AED 455 total
includes taxes & fees
12 Dec - 13 Dec
Casa Vacanze Le Case
Property grounds
Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana
10.0 out of 10, Exceptional, (1)
"TrÚs bon emplacement par rapport à Sienne et maison spacieuse. Propriétaire agréable "
France
YVES A.
The price is AED 556
AED 697 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Tuscan-style apartment Suitable for families. Pets allowed
Property grounds
Romantic farm in the Sienese hills

Romantic farm in the Sienese hills

Trequanda, Siena
"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 HĂŒgeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is AED 346
AED 748 total
includes taxes & fees
9 Dec - 10 Dec
Romantic farm in the Sienese hills
Property grounds
Dolce Casa 2 Summary:

Dolce Casa 2 Summary:

Arezzo
The price is AED 346
AED 475 total
includes taxes & fees
9 Dec - 10 Dec
Dolce Casa 2 Summary:
Pool
Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana
9.8 out of 10, Exceptional, (74)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is AED 513
AED 898 total
includes taxes & fees
9 Dec - 10 Dec
Apartment House with garden Tuscany Chianti , Florence 15km.
Interior
Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano

Barberino Tavarnelle
9.8 out of 10, Exceptional, (9)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
United States
Craig & Conny M.
The price is AED 635
AED 900 total
includes taxes & fees
9 Dec - 10 Dec
Chianti Craft House Badia a Passignano
1 bedroom, iron/ironing board, free WiFi, bed sheets
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)
" La casa pulitissima ù 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 AED 381
AED 680 total
includes taxes & fees
4 Jan - 5 January 2026
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Fridge, microwave, oven, stovetop
LOVE NEST SIENA YOUR LOVE NEST

LOVE NEST SIENA YOUR LOVE NEST

Toscana
The price is AED 252
AED 582 total
includes taxes & fees
13 Dec - 14 Dec
LOVE NEST SIENA YOUR LOVE NEST
Fridge, oven, stovetop, coffee/tea maker
Charming Siena Countryside Stay

Charming Siena Countryside Stay

Monterongriffoli
The price is AED 577
AED 898 total
includes taxes & fees
9 Dec - 10 Dec
Charming Siena Countryside Stay
Bar (on property)
Exclusive Stone Tower.

Exclusive Stone Tower.

Casciano
9.8 out of 10, Exceptional, (7)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
The price is AED 381
AED 637 total
includes taxes & fees
6 Jan - 7 January 2026
Exclusive Stone Tower.
Fridge, microwave, oven, stovetop
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA

San Donato
The price is AED 338
AED 984 total
includes taxes & fees
9 Dec - 10 Dec
DOLCE CUORE LUXE APARTMENT FLORENCE CHIANTI AREA
Outdoor pool
House with pool for 4 pax

House with pool for 4 pax

Casole d'Elsa
9.4 out of 10, Exceptional, (3)
"Besser kann man es nicht haben. Den Pool hatten wir gefĂŒhlt immer fĂŒr uns alleine. Die Lage der Unterkunft erlaubt es uns schnell in Siena und San Gimignano zu sein, auch die anderen SehenswĂŒrdigkeiten 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 AED 599
AED 1,155 total
includes taxes & fees
2 Jan - 3 January 2026
House with pool for 4 pax
Terrace/patio
Casa Da Vinci for two

Casa Da Vinci for two

Castiglion fibocchi
8.0 out of 10, Very Good, (1)
"Sauber gemĂŒtlich, nette AtmosphĂ€re Einrichtung ist ausreichend."
Germany
Perdita I.
The price is AED 171
AED 291 total
includes taxes & fees
31 Dec - 1 January 2026
Casa Da Vinci for two
2 bedrooms, internet, bed sheets
Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta
9.6 out of 10, Exceptional, (25)
"Loved the property and views,the owner was very helpful and informative would definitely come back"
United States
Andy P.
The price is AED 355
AED 1,090 total
includes taxes & fees
29 Dec - 30 Dec
Wonderful Tuscan farmhouse with large spaces and panoramic views
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)
"Pros: Die familiĂ€re Aufnahme und UnterstĂŒtzung war sehr angenehm."
Germany
Anonymous traveler
The price is AED 365
AED 587 total
includes taxes & fees
8 Jan - 9 January 2026
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Terrace/patio
mini house with park, in the province of Siena, btw Valdichiana and Val d'Orcia

mini house with park, in the province of Siena, btw Valdichiana and Val d'Orcia

Sinalunga
8.0 out of 10, Very Good, (2)
"It seemed like a beautiful spot,but ws had tocancel at the last minute due to illness. I hope we can reschedule some day."
Canada
Robert R.
The price is AED 528
AED 609 total
includes taxes & fees
9 Dec - 10 Dec
mini house with park, in the province of Siena, btw Valdichiana and Val d'Orcia
Property grounds
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Monteriggioni
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is AED 1,035
AED 1,471 total
includes taxes & fees
9 Dec - 10 Dec
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
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 Italia

Hotel Italia

10/10 Excellent
"This was a short stay for us in Siena. A great hotel. Friendly staff and the best bargain best breakfast we have had in Italy. Highly recommended"
Phil 1-night trip
Posted 3 days ago
Hotel Italia

Explore a world of travel with Expedia