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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.

  • Showing 1-50 of 300+
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    Exceptional! 5/5
    (5 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 10
    Villa #8042755
    5
    Viewed 22 times in the last 48 hours
      Exceptional! 5/5
      (4 reviews)
      avg/night
      • 1 BR
      • 1 BA
      • Sleeps 4
      Villa #654136vb
      4
      Viewed 11 times in the last 48 hours
        avg/night
        • 6 BR
        • 4 BA
        • Sleeps 12
        Villa #8159492
        1
        Viewed 14 times in the last 48 hours
          Exceptional! 5/5
          (29 reviews)
          avg/night
          • 5 BR
          • 6 BA
          • Sleeps 12
          Villa #281961vb
          29
          Viewed 5 times in the last 48 hours
            • 5 BR
            • 5 BA
            • Sleeps 13
            Villa #604892vb
            Viewed 24 times in the last 48 hours
              • 6 BR
              • 5 BA
              • Sleeps 12
              Multiple rentals Villa #76109
              8
              Viewed 16 times in the last 48 hours
                Very Good! 4/5
                (5 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Cottage #696005vb
                5
                Viewed 13 times in the last 48 hours
                  • 3 BR
                  • 3 BA
                  • Separate Toilet
                  • Sleeps 7
                  Villa #8043542
                  3
                    • 1 BR
                    • Sleeps 3
                    Chateau / Country House #2031854
                    7
                      • 5 BR
                      • 2 BA
                      • Sleeps 10
                      Chateau / Country House #6863996
                      Viewed 5 times in the last 48 hours
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        Multiple rentals Apartment #1206876
                        Viewed 7 times in the last 48 hours
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          Multiple rentals Apartment #1206876
                          3
                          Viewed 6 times in the last 48 hours
                            • 3 BR
                            • 3 BA
                            • Sleeps 6
                            Villa #6509814
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              House #2343140
                              1
                              Viewed 7 times in the last 48 hours
                                Wonderful! 4.9/5
                                (12 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • Sleeps 10
                                Villa #45144vb
                                12
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Multiple rentals Chateau / Country House #454623
                                  1
                                  Viewed 10 times in the last 48 hours
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6
                                    Multiple rentals Villa #1050128
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Multiple rentals Apartment #489852
                                      8
                                        Excellent! 4.7/5
                                        (6 reviews)
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 11
                                        Multiple rentals Villa #76109
                                        6
                                        Viewed 7 times in the last 48 hours
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 3
                                          Multiple rentals Apartment #1206876
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            Cottage #2211388
                                            1
                                            Viewed 12 times in the last 48 hours
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 3
                                              Multiple rentals Villa #6721451
                                              Viewed 8 times in the last 48 hours
                                                Exceptional! 5/5
                                                (51 reviews)
                                                avg/night
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                Multiple rentals Villa #64960
                                                51
                                                Viewed 10 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 20 times in the last 48 hours
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Villa #79371
                                                    2
                                                    Viewed 12 times in the last 48 hours
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      Multiple rentals Villa #79371
                                                      Viewed 6 times in the last 48 hours
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Multiple rentals Villa #6721451
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          Multiple rentals Villa #6721451
                                                          Viewed 18 times in the last 48 hours
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Multiple rentals Villa #6721451
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Multiple rentals Apartment #38930
                                                              3
                                                              Viewed 23 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (4 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Separate Toilet
                                                                • Sleeps 6
                                                                Multiple rentals House #38930
                                                                4
                                                                Viewed 14 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Multiple rentals Villa #79371
                                                                  Viewed 7 times in the last 48 hours
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Multiple rentals Apartment #79371
                                                                    1
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Multiple rentals Villa #79371
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Villa #1150760
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2
                                                                          Multiple rentals Villa #6721451
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 5 BA
                                                                            • Sleeps 11
                                                                            Villa #6556510
                                                                            Viewed 5 times in the last 48 hours
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              House #2343150
                                                                              4
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 5
                                                                                Castle #1751580
                                                                                2
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Apartment #2343144
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    Apartment #2343151
                                                                                      Wonderful! 4.9/5
                                                                                      (33 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 5
                                                                                      Apartment #197862vb
                                                                                      33
                                                                                      Viewed 30 times in the last 48 hours
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                        Multiple rentals House #30993
                                                                                        22
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          Multiple rentals Chateau / Country House #454623
                                                                                          1
                                                                                            Excellent! 4.7/5
                                                                                            (3 reviews)
                                                                                            avg/night
                                                                                            • Studio
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Multiple rentals House #76109
                                                                                            3
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Chateau / Country House #1301990
                                                                                              3
                                                                                              Viewed 9 times in the last 48 hours
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                House #2293968
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Apartment #2293992
                                                                                                  1
                                                                                                  • 1 - 50 of 300+

                                                                                                  Gaiole In Chianti Holiday Apartments & Villas (300+)

                                                                                                   

                                                                                                  Recent Reviews

                                                                                                  lovely villa for friends and family holidays

                                                                                                  5 of 5
                                                                                                  Our time here has been excellent with a great tennis court, swimming pool and villa. Great welcome from the housekeeper - despite him speaking no English - we were able to understand the basics! We would recommend going to Radda, Florence and Sienna with some amazing sights. Advise pre-booking some of the tickets for the museums in Florence so that you can avoid the queues. Do look at the great range of guide books in the drawers. There are some great restaurants in the area, one we especially liked was Malborghetto in Lecchi. Amazing views and a great house to be based from. Well maintained swimming pool and tennis court. Very relaxed time - fantastic time base to explore the area and also excellent base to chill. Rustic charm - next year they are looking at extending which sounds very exciting. Would love to come back some day. The Britton family
                                                                                                  • Review Submitted: 19-Apr-2017
                                                                                                  • Date of Stay: Aug 2016

                                                                                                  Very good!

                                                                                                  4 of 5
                                                                                                  Everything was ok! We've made a lot of visits around Radda and that was amazing to discover Tuscany ! The villa was just like the pictures and the children were very happy ! Finally, we bought some wine near the house, very good ! Petra is very sweet and she can answer at all the questions, even in a bad english ;-) ! Thank you very much! Benedicte
                                                                                                  • Review Submitted: 14-Apr-2017
                                                                                                  • Date of Stay: Aug 2016

                                                                                                  Special stay in a special place

                                                                                                  5 of 5
                                                                                                  My mother and I stopped in Casanova Maguire in September 2017 and had the perfect holiday. The apartment has everything you would possibly need and much more besides, the owners have thought of everything. The owner was attentive courteous and extremely helpful, and clearly has excellent taste; the apartment has been tastefully renovated to a very high standard, maintaining many original features. The location and borgo are simply blissful, in short I could never recommend this apartment enough. Perfect!!!
                                                                                                  • Review Submitted: 02-Feb-2017
                                                                                                  • Date of Stay: Sep 2016