Photo by Karen Dean

Search Vacation Homes in Gaiole in Chianti

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Vacation Homes in Gaiole in Chianti

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

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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Villa Sofia Jacuzzi® Spa
Spa

Villa Sofia Jacuzzi® Spa

10.0 out of 10, Exceptional, (1)
"The service provided by Maria and crew was amazing! From helpful suggestions to making reservations, their local knowledge made our stay an ease. Everything was as pictured and exceeded our expectations. Plus the town is cute with a wonderful restaurant in the center which we ended up going to three nights in a row and was pleasantly blown away each visit. Definitely need a car but other than that no complaints. I'll recommend and will come again! "
The price is SAR 737
SAR 1,092 total
includes taxes & fees
20 Jul - 21 Jul
Villa Sofia Jacuzzi® Spa
Casa Vacanze Le Case
Outdoor pool

Casa Vacanze Le Case

9.0 out of 10, Wonderful, (7)
"Situata in una posizione ideale per trascorrere un momento di relax accompagnati da una vista eccezionale. Davvero bella location."
The price is SAR 473
SAR 543 total
includes taxes & fees
20 Jul - 21 Jul
Casa Vacanze Le Case
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Dining

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

10.0 out of 10, Exceptional, (1)
"I can’t say enough about this wonderful Tuscan gem! We were lucky to find such a beautiful spot to stay. The staff were so friendly and helpful and the cooking class was so much fun! The restaurant was also very good! Thank you for a wonderful stay! "
The price is SAR 561
SAR 666 total
includes taxes & fees
15 Jul - 16 Jul
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Fridge, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
The price is SAR 361
SAR 512 total
includes taxes & fees
15 Jul - 16 Jul
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining

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

10.0 out of 10, Exceptional, (1)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
The price is SAR 577
SAR 804 total
includes taxes & fees
15 Jul - 16 Jul
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Romantic farm in the Sienese hills
Property grounds

Romantic farm in the Sienese hills

The price is SAR 526
SAR 956 total
includes taxes & fees
15 Jul - 16 Jul
Romantic farm in the Sienese hills
Chianti Craft House Badia a Passignano
Interior

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
The price is SAR 653
SAR 921 total
includes taxes & fees
30 Jul - 31 Jul
Chianti Craft House Badia a Passignano
A LUXURY VILLA ON THE HILLS OF FLORENCE
Interior

A LUXURY VILLA ON THE HILLS OF FLORENCE

The price is SAR 43,840
SAR 48,938 total
includes taxes & fees
18 Jul - 19 Jul
A LUXURY VILLA ON THE HILLS OF FLORENCE
The crete senesi
Dining

The crete senesi

10.0 out of 10, Exceptional, (1)
"Une très belle location dans l'environnement magique de la campagne toscane, Paolo est très accueillant , seul bémol la proximité de la route."
The price is SAR 658
SAR 710 total
includes taxes & fees
15 Jul - 16 Jul
The crete senesi
Casa Riccimballa
Aerial view

Casa Riccimballa

The price is SAR 2,730
SAR 3,016 total
includes taxes & fees
15 Jul - 16 Jul
Casa Riccimballa
Room 'L'arco Del Pellegrino' with Wi-Fi and Air Conditioning
Exterior detail

Room 'L'arco Del Pellegrino' with Wi-Fi and Air Conditioning

The price is SAR 364
SAR 484 total
includes taxes & fees
15 Jul - 16 Jul
Room 'L'arco Del Pellegrino' with Wi-Fi and Air Conditioning
Between Florence, Siena and Chianti
Dining

Between Florence, Siena and Chianti

The price is SAR 403
SAR 633 total
includes taxes & fees
22 Jul - 23 Jul
Between Florence, Siena and Chianti
THE CASTELLETTO
Private kitchen

THE CASTELLETTO

The price is SAR 351
SAR 513 total
includes taxes & fees
15 Jul - 16 Jul
THE CASTELLETTO
Exclusive Stone Tower.
Bar (on property)

Exclusive Stone Tower.

9.6 out of 10, Exceptional, (5)
"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...
The price is SAR 346
SAR 609 total
includes taxes & fees
21 Jul - 22 Jul
Exclusive Stone Tower.
ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve
Terrace/patio

ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve

The price is SAR 482
SAR 772 total
includes taxes & fees
17 Jul - 18 Jul
ALESSANDRO HOLIDAY HOUSE - Merlot house with mini-pool in the center of Greve
The little Magician's secret corner
Property grounds

The little Magician's secret corner

The price is SAR 526
SAR 829 total
includes taxes & fees
15 Jul - 16 Jul
The little Magician's secret corner
Vacation Home "Il Botteghino" close to Siena with Wi-Fi
Outdoor dining

Vacation Home "Il Botteghino" close to Siena with Wi-Fi

9.0 out of 10, Wonderful, (2)
"Pros: De locatie was lekker privé, mooi terras, leuk ingericht, goede communicatie, dichtbij een supermarkt (coop) in het dorpje en dichtbij Siena. Ik raad aan de coop in het dorpje als supermarkt te gebruiken, die is groter dan de supermarkten in de stad! Er is veel te doen in de omgeving ook, maar chillen hier is ook heerlijk! Cons: Eigenlijk alleen de muggen, dus ik raad aan muggen spray mee te nemen!"
The price is SAR 818
SAR 974 total
includes taxes & fees
15 Jul - 16 Jul
Vacation Home "Il Botteghino" close to Siena with Wi-Fi
Dolce Casa 2 Summary:
Property grounds

Dolce Casa 2 Summary:

The price is SAR 459
SAR 590 total
includes taxes & fees
16 Jul - 17 Jul
Dolce Casa 2 Summary:
B&B La Chiantigiana Montevarchi
1 bedroom, WiFi, bed sheets

B&B La Chiantigiana Montevarchi

The price is SAR 302
SAR 425 total
includes taxes & fees
15 Jul - 16 Jul
B&B La Chiantigiana Montevarchi
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free