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Holidaymakers searching for holiday rentals in Cortona also enquired about apartments in Lucca, apartments in San Gimignano and villas in Castelnuovo di Garfagnana

Make a holiday rental home or apartment in Cortona, Italy your home away from home

Cortona is a city of art, history and spirituality, located in Tuscany, Italy. Fifty miles from Florence, and flanked by hills and valleys on both sides, Cortona is the picturesque setting in the film ‘Under the Tuscan Sun’. Cortona has attracted tourists for nearly 400 years, and has changed little during that period. Many people go every year to stay in some of the beautiful apartments and holiday homes in the city, or farmhouses in the beautiful surrounding countryside.

Things to do in Cortona, Italy

A lot of visitors are attracted to Cortona’s medieval architecture, which is embodied by the characteristic steep, narrow streets. The main street – via Nazionale – is the only street in the city which has no gradient. Many locals call it Ruga Piana – or ‘Level Street’. The city walls should be your first port of call, and date back over 3,000 years.

Cortona is steeped in culture, and there are three institutions to visit whilst on holiday in the city. These are the Museo dell'Accademia Etrusca, the Civic and Academy Library and the Historic Civic Archive. The city also boasts many churches which date back hundreds of years.

Being a historic Italian city, Cortona offers visitors a great range of trattorias and pizzerias, as well as traditional Tuscan restaurants which serve fantastic food and fine wines. The city does not possess a raucous nightlife, but there is still a good selection of bars to choose from when relaxing after a busy day of sightseeing.

A visit to Cortona is not complete without a trip into the countryside. If your holiday rental accommodation is based in the city centre, you can even hire a bike to explore the many hills and valleys just a short distance away. Some places of accommodation also offer cycling tours at a small cost.

Places to visit on holiday in Cortona, Italy

If you have several days holiday in Cortona, you may consider visiting the city of Perugia, which is around 50km away. Perugia is a popular tourist destination which is famous for its chocolate. A chocolate festival is held every October. Perugia also boasts some impressive medieval architecture, and is well worth a visit.

Weather in Cortona, Italy

Cortona enjoys a warm, dry climate, with summer temperatures averaging around 24C. July and August are the warmest months and the most popular with visitors. The winters are less busy in terms of tourists, but are still a mild 11C on average.

Flights to Cortona, Italy

There are two main airports to consider when holidaying in Cortona – Rome (FCO), Pisa (PSA) and Florence (FLR). Some budget airlines do fly to Florence Airport, which is nearer (around 110km away), but there is usually more regularity and better offers on services to Rome.

  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (15 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 6
    House #6441811
    15
    Viewed 21 times in the last 48 hours
      Wonderful! 4.9/5
      (8 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 5
      Apartment #856818a
      8
      Viewed 8 times in the last 48 hours
        Wonderful! 4.9/5
        (28 reviews)
        avg/night
        • 2 BR
        • 2 BA
        • Sleeps 5
        Villa #463746
        28
        Viewed 19 times in the last 48 hours
          • 3 BR
          • 1 BA
          • Sleeps 7
          Villa #1856415
          3
          Viewed 20 times in the last 48 hours
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 10
            Cottage #6742795
            1
            Viewed 6 times in the last 48 hours
              Excellent! 4.5/5
              (4 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 6
              Villa #8037836
              4
              Viewed 16 times in the last 48 hours
                Wonderful! 4.8/5
                (4 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                Villa #8003714
                4
                Viewed 18 times in the last 48 hours
                  • 3 BR
                  • 1 BA
                  • Sleeps 5
                  Chateau / Country House #6814586
                  1
                    • 5 BR
                    • 5 BA
                    • Sleeps 10
                    Villa #6506310
                    5
                    Viewed 27 times in the last 48 hours
                      Excellent! 4.7/5
                      (7 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Separate Toilet
                      • Sleeps 4
                      Apartment #6629528
                      7
                      Viewed 8 times in the last 48 hours
                        Wonderful! 4.9/5
                        (9 reviews)
                        avg/night
                        • 4 BR
                        • 4 BA
                        • Sleeps 8
                        Villa #8027623
                        9
                        Viewed 51 times in the last 48 hours
                          Exceptional! 5/5
                          (16 reviews)
                          avg/night
                          • 3 BR
                          • 1 BA
                          • Separate Toilet
                          • Sleeps 6
                          House #2245884
                          16
                          Viewed 16 times in the last 48 hours
                            Exceptional! 5/5
                            (5 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Multiple rentals Apartment #751459
                            5
                            Viewed 13 times in the last 48 hours
                              • 7 BR
                              • 5 BA
                              • Separate Toilet
                              • Sleeps 15
                              Villa #1987671
                              3
                              Viewed 23 times in the last 48 hours
                                Exceptional! 5/5
                                (15 reviews)
                                avg/night
                                • 6 BR
                                • 6 BA
                                • Separate Toilets
                                • Sleeps 12
                                Villa #407902
                                15
                                Viewed 43 times in the last 48 hours
                                  Exceptional! 5/5
                                  (4 reviews)
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • Separate Toilets
                                  • Sleeps 8
                                  Villa #8132824
                                  4
                                  Viewed 11 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (10 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    Multiple rentals Apartment #751459
                                    10
                                    Viewed 12 times in the last 48 hours
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Apartment #681415vb
                                      4
                                        Exceptional! 5/5
                                        (11 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #6786308
                                        11
                                        Viewed 5 times in the last 48 hours
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 10
                                          Villa #8037953
                                          1
                                          Viewed 16 times in the last 48 hours
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 3
                                            Apartment #564235vb
                                            3
                                            Viewed 34 times in the last 48 hours
                                              • 5 BR
                                              • 5 BA
                                              • Separate Toilet
                                              • Sleeps 10
                                              Chateau / Country House #6063350
                                              1
                                              Viewed 17 times in the last 48 hours
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Villa #1856420
                                                2
                                                Viewed 22 times in the last 48 hours
                                                  Excellent! 4.5/5
                                                  (6 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 4 BA
                                                  • Sleeps 10
                                                  Villa #71084
                                                  6
                                                  Viewed 15 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (4 reviews)
                                                    avg/night
                                                    • 8 BR
                                                    • 7 BA
                                                    • Separate Toilet
                                                    • Sleeps 16
                                                    Villa #986615vb
                                                    4
                                                    Viewed 122 times in the last 48 hours
                                                      Exceptional! 5/5
                                                      (11 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 6
                                                      Farmhouse #8028340
                                                      11
                                                      Viewed 10 times in the last 48 hours
                                                        • 6 BR
                                                        • 5 BA
                                                        • Separate Toilet
                                                        • Sleeps 14
                                                        Villa #8121486
                                                        2
                                                        Viewed 30 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (24 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 9
                                                          Chateau / Country House #6028278
                                                          24
                                                          Viewed 17 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (14 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 10
                                                            Farmhouse #16699
                                                            14
                                                            Viewed 7 times in the last 48 hours
                                                              Exceptional! 5/5
                                                              (17 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 4 BA
                                                              • Sleeps 8
                                                              Chateau / Country House #1672839
                                                              17
                                                              Viewed 13 times in the last 48 hours
                                                                • 4 BR
                                                                • 4 BA
                                                                • Sleeps 8
                                                                Farmhouse #769383vb
                                                                3
                                                                Viewed 10 times in the last 48 hours
                                                                  • 5 BR
                                                                  • 2 BA
                                                                  • Sleeps 9
                                                                  Villa #1856418
                                                                  2
                                                                  Viewed 34 times in the last 48 hours
                                                                    Exceptional! 5/5
                                                                    (9 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 5 BA
                                                                    • Sleeps 10
                                                                    Villa #1069180
                                                                    9
                                                                    Viewed 15 times in the last 48 hours
                                                                      Excellent! 4.5/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • Sleeps 8
                                                                      Villa #1403458
                                                                      8
                                                                      Viewed 5 times in the last 48 hours
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 4
                                                                        Villa #1856414
                                                                        5
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          Villa #6790451
                                                                          Viewed 11 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 10
                                                                            Farmhouse #45200vb
                                                                            3
                                                                            Viewed 28 times in the last 48 hours
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Sleeps 10
                                                                              Villa #1150869
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                Farmhouse #97452
                                                                                21
                                                                                  • 9 BR
                                                                                  • 6 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 17
                                                                                  Villa #1845001
                                                                                  1
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    Villa #6790456
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 6
                                                                                      Villa #6790452
                                                                                        • 14 BR
                                                                                        • 10 BA
                                                                                        • Sleeps 30
                                                                                        Farmhouse #8143314
                                                                                        Viewed 19 times in the last 48 hours
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                          House #6777811
                                                                                            • 7 BR
                                                                                            • 9 BA
                                                                                            • Separate Toilets
                                                                                            • Sleeps 14
                                                                                            Villa #1150847
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Villa #1644348
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Condo #6797838
                                                                                                  • 8 BR
                                                                                                  • 8 BA
                                                                                                  • Separate Toilets
                                                                                                  • Sleeps 18
                                                                                                  Villa #6799358
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    Villa #6799332
                                                                                                    • 1 - 50 of 300+

                                                                                                    Cortona Holiday Apartments & Villas (300+)

                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Stunning location.

                                                                                                    5 of 5
                                                                                                    We really enjoyed our stay at Casa del Lupo. The little hamlet is delightful and the views of this quiet valley really stunning. The house had everything we needed and the warm pool was very welcome. We visited Siena, Montepulciano, Castel Rigone, Assisi and Todi and had some great meals out as well as at the house.
                                                                                                    • Review Submitted: 09-Mar-2017
                                                                                                    • Date of Stay: Sep 2016

                                                                                                    Holiday of a lifetimw

                                                                                                    5 of 5
                                                                                                    We had the holiday of a lifetime at the beautiful Villa Quercia. The setting is typically Umbrian/Tuscan and the property itself is lovely. It was spotlessly clean and had everything we needed. The heating on the pool meant that it was at a lovely temperature even early in the season before the sun really gets going. Trestina is the nearest town (10 min drive) and has all the necessary amenities with supermarkets etc. Cortona, Città di Castello and Umbertide are all 25 minutes away, very beautiful and with great restaurants, shops and evening entertainment and markets in the mornings. However, there are also closer restaurants with our favourite place only 5 minutes away in the next village. And we loved that we could by the odd item in the little shop in the village. Christina & Richard were fabulous hosts. They were on hand to offer valuable advice on everything from where to eat to the best places to shop (including the best markets to visit). We loved the fact that we could relax by the wonderful pool during the day and that there were so many lovely small to middle sized towns to visit near by. Fantastic!
                                                                                                    • Review Submitted: 18-Dec-2016
                                                                                                    • Date of Stay: May 2016

                                                                                                    Wonderful

                                                                                                    5 of 5
                                                                                                    Under the guise of celebrating a birthday milestone, I persuaded my family to spend a week in this amazing house. Three generations under one roof and everyone had the most special of times. I can not thank Ashleigh enough for being so patient with me before we confirmed our booking (whilst I checked that the whole family was happy and we could sort flights etc) and then recommending places to eat and visit. Meanwhile on the ground we were greeted by Patritzia who really could not do enough for us - a lasagne and shopping as ordered on arrival and even arranged a trip to a local Olive Oil processing business. She could not have done more. We were also lucky enough to help with the harvesting of olives from the trees in the spectacular garden. This kept the children occupied for a while and even one of them for 4 hours (he was hooked!). A big thank you to Vittoria for being so patient with them all! There was plenty to do nearby - Assisi, Gubbio, Cortona, the Lake which really appealed to all ages. We also went to nearby restaurants and used the wood fired pizza oven twice which the children loved. It is also an idyllic spot with a view that I never tired off. We will all take away some amazing memories and I would recommend this property to anyone. Thank you
                                                                                                    • Review Submitted: 09-Nov-2016
                                                                                                    • Date of Stay: Oct 2016