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Holidaymakers searching for holiday rentals in Gaiole in Chianti also enquired about villas in Cortona, villas in Castellina in Chianti and apartments in Lucca

Make a holiday rental home or villa in Gaiole in Chianti, Italy your home away from home

Gaiole in Chianti is a municipality in the Province of Siena, in the beautiful Italian region of Tuscany. Located just 40kms southeast of Florence and 15kms from Siena, Gaiole in Chianti is easily accessible, and has remained a popular choice with tourists for the last few decades.

The Chianti region is regarded as the ‘Heart of Tuscany’, and is identified by its thousand year-old history of winemaking, and strong gastonomical culture. More than half the area is woodland, making it ideal for a range of outdoor activities.

There is a wide range of accommodation available in Gaiole in Chianti, including luxury villas and rural farmhouses, making a self-catering holiday the best choice of vacation.

Things to do in Gaiole in Chianti, Italy

The Chianti region is one of the most famous wine producing regions in the world, meaning wine tasting forms a huge part of any holiday here. Many wineries offer tasting sessions, and you can turn up by yourself or join an organized tour. Some wineries offer food, and the best thing to do is take your time, and slow your pace to that of the locals.

Gaiole in Chianti has many sites which date back to the 11th and 12th Centuries, including the Castle of Broilo, the Abbey of Coltibuono, and the Pieve of San Marcellino. The Romanesque parish church of Santa Maria e Spaltenna dates back to the 12th Century, and you can enjoy a high-class meal in the surroundings of the old cloister. The picturesque old town warrants a good deal of exploring.

It is also recommended that you get out into the beautiful surrounding countryside, hike in the hills and take in the scenery. The great weather, spectacular scenery and high quality of living have made Gaiole in Chianti ‘Europe’s Most Idyllic Place to Live’, as voted by an expert panel on forbes.com.

Places to visit on holiday in Gaiole in Chianti, Italy

Gaiole in Chianti is part of the Chianti Storico, a historical area which is also home to the other Chianti Classico towns of Castelinna in Chianti and Radda in Chianti, both of which warrant a day visit.

Due to its close proximity to the famous Italian cities of Florence and Siena, it is possible to pay a visit to these cities whilst staying in the Chianti region, but still return to your holiday rental accommodation in the evenings, giving you the best of both worlds.

Weather in Gaiole in Chianti, Italy

Gaiole in Chianti experiences hot summers, which regularly reach over 35C. Due to the fact that you are likely to be spending a lot of time outdoor during your stay here, it may be more comfortable to visit in the spring or autumn, as the temperatures are cooler and more pleasant for outdoor activities.

Flights to Gaiole in Chianti, Italy

Florence Airport (FLR) is just 40km away, but there is a lack of direct flights from UK airports. A cheaper and more viable option is Pisa Airport (PSA), which is around two hour’s drive from the Chianti region, and receives an abundance of flights from budget airlines.

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Viewed 47 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 3229 sq. ft.
Wonderful! 4.9/5
(18 reviews)
avg/night
Premier Partner
18
Viewed 22 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1506 sq. ft.
Exceptional! 5/5
(50 reviews)
avg/night
50
Viewed 20 times in the last 48 hours
  • 5 BR Villa
  • 6 BA
Exceptional! 5/5
(32 reviews)
avg/night
32
Viewed 22 times in the last 48 hours
  • 4 BR House
  • 4 BA
  • 2152 sq. ft.
Wonderful! 4.8/5
(29 reviews)
avg/night
Premier Partner
29
Viewed 17 times in the last 48 hours
  • 5 BR Villa
  • 5 BA
  • 4843 sq. ft.
avg/night
3
Viewed 27 times in the last 48 hours
  • 1 BR Castle
  • 1 BA
  • 1076 sq. ft.
Wonderful! 4.8/5
(24 reviews)
avg/night
Premier Partner
24
Viewed 65 times in the last 48 hours
  • 5 BR Villa
  • 2 BA
  • Separate Toilet
  • 3605 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
6
Viewed 57 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 807 sq. ft.
Wonderful! 4.8/5
(12 reviews)
avg/night
Premier Partner
12
Viewed 16 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1463 sq. ft.
Excellent! 4.6/5
(16 reviews)
avg/night
16
Viewed 17 times in the last 48 hours
  • 2 BR Cottage
  • 2 BA
  • 1033 sq. ft.
Very Good! 4/5
(7 reviews)
avg/night
7
Viewed 64 times in the last 48 hours
  • 3 BR Villa
  • 3 BA
  • 2152 sq. ft.
Wonderful! 4.8/5
(44 reviews)
avg/night
Premier Partner
44
Viewed 7 times in the last 48 hours
  • 5 BR Villa
  • 3 BA
  • 2152 sq. ft.
Wonderful! 4.8/5
(16 reviews)
avg/night
Premier Partner
16
Viewed 30 times in the last 48 hours
  • 4 BR Chateau / Country House
  • 3 BA
  • 3229 sq. ft.
Wonderful! 4.9/5
(29 reviews)
avg/night
Premier Partner
29
Viewed 48 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 2 BA
  • 807 sq. ft.
avg/night
Premier Partner
4
Viewed 20 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 1614 sq. ft.
Wonderful! 4.8/5
(32 reviews)
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Premier Partner
32
  • 1 BR Villa
  • 1 BA
  • 538 sq. ft.
Exceptional! 5/5
(8 reviews)
avg/night
8
Viewed 18 times in the last 48 hours
  • 3 BR Villa
  • 3 BA
  • 2421 sq. ft.
Wonderful! 4.9/5
(37 reviews)
avg/night
37
Viewed 26 times in the last 48 hours
  • 5 BR Villa
  • 5 BA
  • 2475 sq. ft.
Exceptional! 5/5
(20 reviews)
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Premier Partner
20
Viewed 36 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 818 sq. ft.
Wonderful! 4.9/5
(9 reviews)
avg/night
9
Viewed 7 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1291 sq. ft.
avg/night
4
Viewed 25 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 968 sq. ft.
Exceptional! 5/5
(41 reviews)
avg/night
Premier Partner
41
Viewed 41 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 2152 sq. ft.
Excellent! 4.7/5
(15 reviews)
avg/night
Premier Partner
15
Viewed 24 times in the last 48 hours
  • 3 BR Farmhouse
  • 2 BA
  • 1829 sq. ft.
Wonderful! 4.8/5
(16 reviews)
avg/night
Premier Partner
16
Viewed 7 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1614 sq. ft.
Wonderful! 4.8/5
(13 reviews)
avg/night
13
Viewed 17 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 861 sq. ft.
Wonderful! 4.9/5
(12 reviews)
avg/night
Premier Partner
12
Viewed 8 times in the last 48 hours
  • 3 BR Villa
  • 3 BA
  • 1227 sq. ft.
Excellent! 4.7/5
(7 reviews)
avg/night
Premier Partner
7
Viewed 31 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 2 BA
  • 1065 sq. ft.
Excellent! 4.7/5
(12 reviews)
avg/night
12
Viewed 39 times in the last 48 hours
  • 10 BR Villa
  • 11 BA
  • 6996 sq. ft.
avg/night
Viewed 146 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 914 sq. ft.
Wonderful! 4.9/5
(15 reviews)
avg/night
15
Viewed 21 times in the last 48 hours
  • 5 BR Chateau / Country House
  • 3 BA
  • 3229 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
Premier Partner
5
Viewed 17 times in the last 48 hours
  • 2 BR Villa
  • 1 BA
  • 753 sq. ft.
Excellent! 4.7/5
(14 reviews)
avg/night
14
Viewed 51 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 2152 sq. ft.
Exceptional! 5/5
(35 reviews)
avg/night
Premier Partner
35
Viewed 9 times in the last 48 hours
  • 6 BR Villa
  • 4 BA
  • 7500 sq ft
avg/night
2
Viewed 6 times in the last 48 hours
  • 1 BR Barn
  • 1 BA
  • 861 sq. ft.
Wonderful! 4.8/5
(18 reviews)
avg/night
Premier Partner
18
Viewed 27 times in the last 48 hours
  • 6 BR Villa
  • 3 BA
  • Separate Toilet
  • 2690 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
Premier Partner
5
Viewed 5 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 1 BA
  • 1022 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
Premier Partner
7
Viewed 14 times in the last 48 hours
  • 5 BR House
  • 5 BA
  • 3000 sq ft
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4
Viewed 7 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1345 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
7
Viewed 45 times in the last 48 hours
  • 6 BR Villa
  • 5 BA
  • 4500 sq ft
Exceptional! 5/5
(10 reviews)
avg/night
10
Viewed 43 times in the last 48 hours
  • 2 BR Apartment
  • 2 BA
  • 1614 sq. ft.
Exceptional! 5/5
(63 reviews)
avg/night
Premier Partner
63
Viewed 56 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 1076 sq. ft.
Wonderful! 4.9/5
(27 reviews)
avg/night
27
Viewed 32 times in the last 48 hours
  • 1 BR Apartment
  • 1 BA
  • 592 sq. ft.
Exceptional! 5/5
(85 reviews)
avg/night
Premier Partner
85
Viewed 9 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 1506 sq. ft.
Exceptional! 5/5
(27 reviews)
avg/night
Premier Partner
27
Viewed 12 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 1022 sq. ft.
Exceptional! 5/5
(50 reviews)
avg/night
50
Viewed 12 times in the last 48 hours
  • 2 BR Chateau / Country House
  • 1 BA
  • Separate Toilet
  • 785 sq. ft.
Wonderful! 4.8/5
(40 reviews)
avg/night
Premier Partner
40
Viewed 58 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1614 sq. ft.
Wonderful! 4.9/5
(20 reviews)
avg/night
20
Viewed 5 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 1646 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 10 times in the last 48 hours
  • 6 BR Villa
  • 5 BA
  • 4305 sq. ft.
avg/night
Viewed 60 times in the last 48 hours
  • 2 BR Apartment
  • 1 BA
  • 861 sq. ft.
Wonderful! 4.8/5
(15 reviews)
avg/night
15
Viewed 9 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1184 sq. ft.
Wonderful! 4.9/5
(32 reviews)
avg/night
Premier Partner
32

Gaiole In Chianti Holiday Apartments & Villas (300+)

 

Recent Reviews

Super séjour

5 of 5
Très bien accueilli à l´arrivée, ne manque rien dans l’appartement. Tout est fait pour s’y sentir bien, j’y retournerais avec plaisir. Cadre agréable. Je recommande vivement
  • Review Submitted: May 16, 2018
  • Date of Stay: May 2018

Fabulous remote villa

5 of 5
Myself and my family loved the week long stay we had at Simonetta's villa. The setting is glorious, and the views were incredible. The house is roomy, and each room is very generous in size so no-one felt too cramped. The kitchen was great with all the facilities we could need, (just check the cupboards before you go shopping, as there was a lot of olive oil and vinegars etc available to use). The pool was glorious, and there were an assortment of sunny corners to sit in around the property as well. We all really enjoyed attempting to make pizza in the pizza oven (if it goes wrong there is a great pizzeria in the next village along). We loved the remoteness of this property - but be warned you will need a car to stay here, and the nearest supermarket is a good 25 minute drive. We loved getting to all the hilltop medieval towns which were all easily driveable. We also enjoyed the 20 min walk to the local vineyard (Tolaini) where we did a great tasting. Overall a fantastic stay - which was very much complimented by Simonetta's amazing chocolate torte that she left for us as a welcome gift.
  • Review Submitted: May 14, 2018
  • Date of Stay: May 2018