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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

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 AED 2,289
AED 2,662 total
includes taxes & fees
26 Jun - 27 Jun
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
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.
Villa with large garden in the Chianti hills
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 AED 571
AED 822 total
includes taxes & fees
1 Jul - 2 Jul
Chianti Craft House Badia a Passignano
Pool

Agriturismo I Borghi - Cacao Apartment with Pool in San Gimignano

Agriturismo I Borghi - Cacao Apartment with Pool in San Gimignano
San Gimignano
The price is AED 1,543
AED 1,564 total
includes taxes & fees
28 Jun - 29 Jun
Agriturismo I Borghi - Cacao Apartment with Pool in San Gimignano
Outdoor dining

The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 1,156
AED 1,319 total
includes taxes & fees
30 Jun - 1 Jul
The Arch Among the Hills of Castellina
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 1,126
AED 1,510 total
includes taxes & fees
28 Jun - 29 Jun
Charming Siena Countryside Stay
Outdoor dining

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 901
AED 1,126 total
includes taxes & fees
30 Jun - 1 Jul
Casa Marisa in Castellina in Chianti
Pool

Donatello Apartment

Donatello Apartment
San Gersolé-torre Rosse
Donatello Apartment
Outdoor dining

Giotto Apartment with garden

Giotto Apartment with garden
San Gersolé-torre Rosse
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was as pictured – very clean, very comfortable, very bright. The entire grounds were beautiful. Hosts were great and helpful. We wish we stayed longer – and plan on doing so in the future."
United States
Todd G.
The price is AED 1,368
AED 2,191 total
includes taxes & fees
28 Jun - 29 Jun
Giotto Apartment with garden
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 AED 335
AED 627 total
includes taxes & fees
28 Jun - 29 Jun
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Exterior

'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi

'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi
San Gimignano
The price is AED 2,452
AED 2,464 total
includes taxes & fees
26 Jun - 27 Jun
'La Ripa - Apartment Il Fienile' with Shared Pool & Wi-Fi
Outdoor dining

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Colle Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"Schöne Zimmer, Dusche sehr modern und sehr sauber, Fernseher mit Internet-Anschluss sehr gut"
Germany
Rupert H.
The price is AED 1,514
AED 1,701 total
includes taxes & fees
27 Jun - 28 Jun
Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Pool

The Leonardo Apartment, at the second floor, consist of a large living room and one spacious master double bedroom, a mezzanine with a queen-size bed, one bathroom with shower, and fully equipped kitchen with view on the surrounding countryside.The suite

The Leonardo Apartment, at the second floor, consist of a large living room and one spacious master double bedroom, a mezzanine with a queen-size bed, one bathroom with shower, and fully equipped kitchen with view on the surrounding countryside.The suite
San Gersolé-torre Rosse
The price is AED 1,368
AED 2,107 total
includes taxes & fees
1 Jul - 2 Jul
The Leonardo Apartment, at the second floor, consist of a large living room and one spacious master double bedroom, a mezzanine with a queen-size bed, one bathroom with shower, and fully equipped kitchen with view on the surrounding countryside.The suite
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 AED 1,137
AED 1,935 total
includes taxes & fees
30 Jun - 1 Jul
Upon request, we can arrange a breakfast basket for €18 per person:sweet or savory. For more details, please write to info@torrerossa.com
Fridge, microwave, oven, stovetop

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Vaggio
The price is AED 2,483
AED 2,496 total
includes taxes & fees
28 Jun - 29 Jun
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Exterior detail

Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi

Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
Scrofiano
The price is AED 1,628
AED 1,712 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
Property grounds

Vasari Apartment is set in the charming, hilly landscape between Florence and the Chianti region, and gives off a pleasant feeling of comfort and privacy. Vasari Apartment has three double bedrooms, three bathrooms, a large living room and a kitchen full

Vasari Apartment is set in the charming, hilly landscape between Florence and the Chianti region, and gives off a pleasant feeling of comfort and privacy. Vasari Apartment has three double bedrooms, three bathrooms, a large living room and a kitchen full
Impruneta
10.0 out of 10, Exceptional, (1 review)
"…."
Italy
Giuseppe F.
The price is AED 2,275
AED 3,603 total
includes taxes & fees
30 Jun - 1 Jul
Vasari Apartment is set in the charming, hilly landscape between Florence and the Chianti region, and gives off a pleasant feeling of comfort and privacy. Vasari Apartment has three double bedrooms, three bathrooms, a large living room and a kitchen full
Property grounds

Holday at Poggettone

Holday at Poggettone
Monteroni d'Arbia
The price is AED 601
AED 926 total
includes taxes & fees
29 Jun - 30 Jun
Holday at Poggettone
Property grounds

Elegant 3 bedroom apt, in historical Villa, shared pool, parking, 3km to Center

Elegant 3 bedroom apt, in historical Villa, shared pool, parking, 3km to Center
Oltrarno
10.0 out of 10, Exceptional, (1 review)
"Geweldig. Alles klopt aan deze fantastische plek. Ontvangst, gastvrijheid, inrichting, geschiedenis en locatie. Echt prachtig"
Netherlands
Irene P.
The price is AED 4,264
AED 5,777 total
includes taxes & fees
22 Jul - 23 Jul
Elegant 3 bedroom apt, in historical Villa, shared pool, parking, 3km to Center
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 AED 468
AED 536 total
includes taxes & fees
2 Jul - 3 Jul
Casa Vacanze Le Case
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"I absolutely loved staying here and would stay here again! Very clean and vibrant facility. The glamping tent was such a fun place to stay. Some of the best sleep I've ever had while traveling. The staff was friendly, and the convenience of having a market and restaurant on-site was wonderful. Excellent food and service! The bus line runs right out front so it's super easy to get into the touristy section of Florence. The Ridemovi bike share bikes were nearby as well, which made transportation so easy. This place far exceeded my expectations. Highly recommended!"
Jason 3-night trip
Posted 3 hours ago
Hu Firenze Camping In Town