HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr

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.

Use filters to narrow your search results!

Gaiole in Chianti Holiday Apartments & Villas (5,655)

  • 1 - 50 of 5,655
Additional service fee may apply.
    • 3 BR
    • 3 BA
    • Sleeps 6
    45
      • 2 BR
      • 1 BA
      • Sleeps 4
      17
        • 2 BR
        • 1 BA
        • Separate Toilet
        • Sleeps 6
        4
          • 1 BR
          • 1 BA
          • Sleeps 4
          3
            • 12 BR
            • 11 BA
            • Sleeps 24
            6
              • 2 BR
              • 2 BA
              • Sleeps 5
                • 2 BR
                • 1 BA
                • Sleeps 4
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  1 Review
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      1 Review
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        3
                          • 5 BR
                          • 6 BA
                          • Sleeps 12
                          28
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            10
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              3
                                • 1 BR
                                • Sleeps 3
                                4
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 10
                                  11
                                    • 6 BR
                                    • 5 BA
                                    • Sleeps 12
                                    7
                                      • 5 BR
                                      • 4 BA
                                      • Sleeps 11
                                      5
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 5
                                        1 Review
                                          • 5 BR
                                          • 4 BA
                                          • Sleeps 10
                                          3
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            4
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              6
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                  • Studio
                                                  • 1 BA
                                                  • Sleeps 4
                                                  1 Review
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                      • Studio
                                                      • 1 BA
                                                      • Sleeps 2
                                                      3
                                                        • 6 BR
                                                        • 4 BA
                                                        • Sleeps 10
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          4
                                                            • 6 BR
                                                            • 4 BA
                                                            • Sleeps 12
                                                            1 Review
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 5
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                3
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 3
                                                                  2 Reviews
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          1 Review
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                              • 8 BR
                                                                              • 7 BA
                                                                              • Sleeps 17
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                1 Review
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 4
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 3
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 8
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 4
                                                                                              • 1 - 50 of 5,655
                                                                                               

                                                                                              Recent Reviews

                                                                                              Charming Villa and Host. A very peaceful and relaxing stay.

                                                                                              5 of 5
                                                                                              We have had a lovely week in Gaiole in Chianti, this villa was so peaceful. We spent a good deal of our time relaxing by the pool. My husband a keen cyclist spent his mornings cycling L'Eroica and Strade Bianche (white roads). There are plenty of pretty little towns to visit not to mention only half an hour to Siena. We received a very warm welcome from our host Franco who gave us lots of advise and when we had a little hiccup he was very quick to respond. The villa had all we wanted and was clean and spacious. We hope to return one day.
                                                                                              • Review Submitted: 20-Aug-2016
                                                                                              • Date of Stay: Aug 2016

                                                                                              Beautiful and relaxing--a great place to unwind

                                                                                              5 of 5
                                                                                              Our stay at Le Logge was wonderful and our hosts could not have been more gracious, wish we could have stayed longer. The villa is in a great secluded location that allows you to get away from everything. The accommodations were five star. Four of stayed at the villa for eight days and it could have comfortably accommodated six adults. The property is ideally located for a day trip to Florence, shopping or dinner in Siena, or visits to the many wineries in the area. Highly recommend the taste of Tuscany dinner prepared by our host Enzo and served by his exceptional sons. The property is an old farm property that was exceptionally renovated with as much attention payed to the surrounding grounds and gardens that offer beautiful views of vineyards and olive groves. We would go back again in a heartbeat and recommend it to all. Thanks for letting us rent your property Enzo and Liliana--you have a great property and family!!!
                                                                                              • Review Submitted: 21-Jul-2016
                                                                                              • Date of Stay: Jun 2016

                                                                                              Great base for enjoyable Tuscan holiday - but you'll need a car.

                                                                                              4 of 5
                                                                                              An attractive and well appointed/equipped apartment in a tasteful complex, situated high above the small town of Giaole. Patio offers great views of town and ideal location for early morning or late evening refreshments. Excellent support from workers on and off site. We didn't use the communal pool, but particularly enjoyed the opportunities for biking using the cycles provided with the apartment - though the hills are a good challenge in the heat! Siena, Florence, San Gimiagno all within easy reach by car, which we would suggest is essential if staying more than a few days. The owner, Phil, was a great correspondent and couldn't have been more helpful.
                                                                                              • Review Submitted: 12-Jul-2016
                                                                                              • Date of Stay: Jun 2016