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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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  • Showing 1-50 of 300+
Additional service fee may apply.
    Very Good! 4.0/5
    (5 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 4
    Cottage #696005vb
    5
    Viewed 21 times in the last 48 hours
      • 2 BR
      • 1 BA
      • Sleeps 6
      House #1667307
      3
      Viewed 7 times in the last 48 hours
        Exceptional! 5.0/5
        (48 reviews)
        avg/night
        • 3 BR
        • 3 BA
        • Sleeps 6
        Multiple rentals Villa #64960
        48
        Viewed 20 times in the last 48 hours
          • 1 BR
          • Sleeps 3
          Chateau / Country House #2031854
          6
            Exceptional! 5.0/5
            (29 reviews)
            avg/night
            • 5 BR
            • 6 BA
            • Sleeps 12
            Villa #281961vb
            29
            Viewed 9 times in the last 48 hours
              • 2 BR
              • Separate Toilet
              • Sleeps 4
              Cottage #1301990
              3
              Viewed 10 times in the last 48 hours
                Wonderful! 4.9/5
                (22 reviews)
                avg/night
                • 1 BR
                • 1 BA
                • Sleeps 2
                Multiple rentals House #30993
                22
                Viewed 6 times in the last 48 hours
                  Wonderful! 4.8/5
                  (19 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                  Multiple rentals Villa #64960
                  19
                  Viewed 5 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    House #769233vb
                    Viewed 20 times in the last 48 hours
                      • 4 BR
                      • 3 BA
                      • Sleeps 10
                      Villa #45144vb
                      12
                        • 3 BR
                        • 3 BA
                        • Separate Toilet
                        • Sleeps 7
                        Villa #8043542
                        2 Reviews
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          Apartment #2293992
                          1 Review
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            House #2293934
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              House #2343140
                              1 Review
                              Viewed 6 times in the last 48 hours
                                • 1 BR
                                • 1 BA
                                • Sleeps 3
                                Multiple rentals Chateau / Country House #454623
                                1 Review
                                  • 6 BR
                                  • 4 BA
                                  • Sleeps 12
                                  Villa #8159492
                                  1 Review
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 10
                                    Villa #8042755
                                    2 Reviews
                                      • 3 BR
                                      • 3 BA
                                      • Separate Toilet
                                      • Sleeps 7
                                      Villa #908036
                                      11
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Multiple rentals Apartment #1206876
                                        3
                                        Viewed 5 times in the last 48 hours
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Multiple rentals Apartment #38930
                                          3
                                            • 2 BR
                                            • 1 BA
                                            • Separate Toilet
                                            • Sleeps 6
                                            Multiple rentals House #38930
                                            4
                                            Viewed 12 times in the last 48 hours
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              Multiple rentals Villa #6721451
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                Multiple rentals Villa #6721451
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  Multiple rentals Villa #6721451
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 3
                                                    Multiple rentals Villa #6721451
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 3
                                                      Multiple rentals Villa #6721451
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Villa #1150760
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          Multiple rentals Villa #79371
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Multiple rentals Villa #79371
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 3
                                                              Multiple rentals Apartment #79371
                                                              1 Review
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Multiple rentals Villa #79371
                                                                2 Reviews
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 3
                                                                  Multiple rentals Villa #79371
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 4
                                                                    House #2343150
                                                                    4
                                                                    Viewed 21 times in the last 48 hours
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 5
                                                                      Cottage #2211388
                                                                      1 Review
                                                                      Viewed 7 times in the last 48 hours
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        Multiple rentals Apartment #489852
                                                                        7
                                                                          • 5 BR
                                                                          • 4 BA
                                                                          • Sleeps 10
                                                                          Villa #8155527
                                                                          4
                                                                          Viewed 9 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Multiple rentals Apartment #1206876
                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Apartment #2343139
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                Multiple rentals Chateau / Country House #454623
                                                                                1 Review
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  Castle #1751580
                                                                                  2 Reviews
                                                                                    • 5 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 13
                                                                                    Villa #604892vb
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      Castle #1751582
                                                                                      2 Reviews
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        Multiple rentals Apartment #489852
                                                                                        4
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          House #2293968
                                                                                            avg/night
                                                                                            • 6 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 10
                                                                                            House #6613507
                                                                                            Viewed 14 times in the last 48 hours
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 3
                                                                                              Multiple rentals Apartment #1206876
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 5
                                                                                                Apartment #1680263
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 3
                                                                                                  Apartment #2448656
                                                                                                  • 1 - 50 of 300+

                                                                                                  Gaiole In Chianti Holiday Apartments & Villas (300+)

                                                                                                   

                                                                                                  Recent Reviews

                                                                                                  Paradise in Tuscany!

                                                                                                  5 of 5
                                                                                                  We stayed at this stunning villa for 6 nights and were blown away. The pictures are nice but the villa itself has to be seen to be believed. We were 2 couples and we stayed in the 3 bedroom upstairs apartment and absolutely loved it. Less than a half hour from Sienna and about 1 hour from many popular destinations (San Gimignano, Montalcino, Montepulciano), we really had the time of our lives. We decided to take the italian cooking class with Enzo (the owner of the villa) and his 2 sons (Duccio and Max) and it was a night to remember. The sweetest people you can imagine and just mouth watering food and wine. They come to the villa, prepare their class, and then treat you to a 4 course meal of typical Tuscan cuisine. Definitely a highlight of our trip. Needless to say, we 100% recommend the villa. Romantic getaway, family vacation, travelling with friends, it's the perfect place to go. We were given a tour of the 2 bedroom apartment at the ground floor, equally stunning but we liked the fact that the upstairs had more than 1 bathroom. We left the villa with heavy hearts but I am certain that we will return one day. Can't wait!
                                                                                                  • Review Submitted: 01-Dec-2016
                                                                                                  • Date of Stay: Nov 2016

                                                                                                  Heavenly, beautiful, peacefull

                                                                                                  5 of 5
                                                                                                  The villa is more than I dreamed it would be. Comfortable, fully applianced kitchen, beautiful scenery and so close to Siena - 10 minutes Italian driver; 20 min. American driver! We were there for 3 Septembers - 2014/15/16 that's how much we liked it. the host family were exceptionally kind and generous. Anyone who spends time there will be the better for it. We loved every minute.
                                                                                                  • Review Submitted: 10-Oct-2016
                                                                                                  • Date of Stay: Sep 2016

                                                                                                  Review for stay from 22 September 2016 to 25 September 2016

                                                                                                  5 of 5
                                                                                                  My favorite days in Italy! Beautiful place, delicious food and impeccable service!
                                                                                                  • Review Submitted: 03-Oct-2016
                                                                                                  • Date of Stay: Sep 2016