Villas in Cortona and Holiday rentals - Holiday Lettings - Holiday Rentals Cortona

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4,197 Holiday homes

    57

    Holiday farmhouse with swimming pool in Creti

    Cortona / Creti

    6 14 7 nights min

    • 6 bedrooms
    • sleeps 14
    • 7 nights min
    • Swimming pool
    • Child friendly
    • Private garden

    from £355 / night

    £2,481 - £3,771 / week

    Book View

    from £355 / night

      31

      Cortona holiday villa rental

      Province of Arezzo / Cortona

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Swimming pool
      • Child friendly
      • Air conditioning

      from £248 / night

      £1,489 - £3,126 / week

      Book View

      from £248 / night

      (1) Excellent 

        19

        Holiday apartment with shared pool in Fratta Santa Caterina

        Cortona / Fratta Santa Caterina

        1 2 min stay varies

        • 1 bedroom
        • sleeps 2
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 15 km
        • Swimming pool

        from £69 / night

        £527 - £733 / week

        Book View

        from £69 / night

          26

          Holiday villa with swimming pool in Cortona

          Province of Arezzo / Cortona

          4 8 min stay varies

          • 4 bedrooms
          • sleeps 8
          • min stay varies
          • Swimming pool
          • Child friendly
          • Air conditioning

          from £247 / night

          £1,477 - £3,102 / week

          Book View

          from £247 / night

          (4) Very Good 

            24

            Holiday cottage with shared pool in Cortona

            Province of Arezzo / Cortona

            2 4 3 nights min

            • 2 bedrooms
            • sleeps 4
            • 3 nights min
            • Swimming pool
            • Child friendly
            • Car not necessary

            from £139 / night

            £973 / week

            Book View

            from £139 / night

            (1) Excellent 

              20

              Holiday apartment with shared pool in Fratta Santa Caterina

              Cortona / Fratta Santa Caterina

              2 3 min stay varies

              • 2 bedrooms
              • sleeps 3
              • min stay varies
              • Beach / lakeside relaxation
              • Nearest beach 15 km
              • Swimming pool

              from £67 / night

              £504 - £699 / week

              Book View

              from £67 / night

              (6) Excellent 

                27

                Cortona holiday cottage rental

                Province of Arezzo / Cortona

                3 6 3 nights min

                • 3 bedrooms
                • sleeps 6
                • 3 nights min
                • Swimming pool
                • Child friendly
                • Pet friendly

                from £138 / night

                £966 / week

                Book View

                Responds fast!
                avg. 1 hour 1 minutes

                from £138 / night

                  42

                  Farinaio holiday apartment rental

                  Cortona / Farinaio

                  2 4 2 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 2 nights min
                  • Swimming pool
                  • Child friendly
                  • Ask about pets

                  from £114 / night

                  £794 / week

                  Book View

                  from £114 / night

                    29

                    Mercatale holiday villa rental

                    Cortona / Mercatale

                    6 11 7 nights min

                    • 6 bedrooms
                    • sleeps 11
                    • 7 nights min
                    • Swimming pool
                    • Child friendly
                    • Private garden

                    from £411 / night

                    £2,878 - £3,969 / week

                    Book View

                    from £411 / night

                    (11) Very Good 

                    Certificate of Excellence

                      46

                      Holiday apartment rental

                      Cortona / Centoia

                      1 3 min stay varies

                      • 1 bedroom
                      • sleeps 3
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Nearest beach 118 km
                      • Swimming pool

                      Certificate of Excellence

                      from £79 / night

                      £497 - £645 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 59 minutes

                      from £79 / night

                      (3) Very Good 

                        19

                        Holiday apartment with shared pool in Fratta Santa Caterina

                        Cortona / Fratta Santa Caterina

                        1 4 min stay varies

                        • 1 bedroom
                        • sleeps 4
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 15 km
                        • Swimming pool

                        from £74 / night

                        £561 - £790 / week

                        Book View

                        from £74 / night

                          45

                          Holiday apartment with shared pool in Cortona

                          Province of Arezzo / Cortona

                          1 2 2 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 2 nights min
                          • Swimming pool
                          • Child friendly
                          • Pet friendly

                          from £79 / night

                          £546 / week

                          Book View

                          from £79 / night

                            30

                            Holiday home with swimming pool in Cortona

                            Province of Arezzo / Cortona

                            6 11 7 nights min

                            • 6 bedrooms
                            • sleeps 11
                            • 7 nights min
                            • Swimming pool
                            • Child friendly
                            • Air conditioning

                            from £213 / night

                            £1,489 - £2,481 / week

                            Book View

                            from £213 / night

                            (12) Excellent 

                              19

                              Apartment rental in Ruffignano

                              Cortona / Ruffignano

                              2 5 4 nights min

                              • 2 bedrooms
                              • sleeps 5
                              • 4 nights min
                              • Nearest beach 0 km
                              • Child friendly
                              • Ask about pets

                              from £124 / night

                              £844 - £1,696 / week

                              Book View

                              from £124 / night

                              (9) Excellent 

                                26

                                Holiday villa rental

                                Cortona / Montecchio

                                6 12 7 nights min

                                • 6 bedrooms
                                • sleeps 12
                                • 7 nights min
                                • Swimming pool
                                • Child friendly
                                • Air conditioning

                                from £284 / night

                                £1,985 - £3,473 / week

                                Book View

                                from £284 / night

                                (2) Excellent 

                                  36

                                  Holiday villa with swimming pool in Cortona

                                  Province of Arezzo / Cortona

                                  7 14 min stay varies

                                  • 7 bedrooms
                                  • sleeps 14
                                  • min stay varies
                                  • Nearest beach 19 km
                                  • Swimming pool
                                  • Child friendly

                                  from £312 / night

                                  £2,181 / week

                                  Book View

                                  from £312 / night

                                    21

                                    Holiday apartment with shared pool in Cortona

                                    Province of Arezzo / Cortona

                                    2 4 7 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 7 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Pet friendly

                                    from £107 / night

                                    £745 - £943 / week

                                    Book View

                                    from £107 / night

                                    (4) Excellent 

                                      39

                                      Cottage rental in Cortona

                                      Province of Arezzo / Cortona

                                      1 6 4 nights min

                                      • 1 bedroom
                                      • sleeps 6
                                      • 4 nights min
                                      • Child friendly
                                      • Car not necessary
                                      • Pet friendly

                                      from £85 / night

                                      £591 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 37 minutes

                                      from £85 / night

                                      (15) Excellent 

                                        53

                                        Holiday villa in Cortona

                                        Province of Arezzo / Cortona

                                        2 5 min stay varies

                                        • 2 bedrooms
                                        • sleeps 5
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Nearest beach 10 km
                                        • Swimming pool
                                        “Paradise!” Had a one week stay at Villa Rosa and fell in love with the house, the gardens and Cortona. This really is a peice of Italian paradise - the house is beautifully appointed...spacious, modern but still a taste of Italian living. IT was the best 7 days :0)

                                        from £269 / night

                                        £1,884 / week

                                        Book View

                                        Responds fast!
                                        avg. 3 hours 38 minutes

                                        from £269 / night

                                        (10) Very Good 

                                          20

                                          Holiday villa in Mercatale di Cortona

                                          Cortona / Mercatale di Cortona

                                          4 10 7 nights min

                                          • 4 bedrooms
                                          • sleeps 10
                                          • 7 nights min
                                          • Nearest beach 23 km
                                          • Swimming pool
                                          • Child friendly

                                          from £139 / night

                                          £973 - £2,747 / week

                                          Book View

                                          Responds fast!
                                          avg. 3 hours 53 minutes

                                          from £139 / night

                                            50

                                            Holiday apartment rental

                                            Cortona / Farinaio

                                            2 4 2 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 2 nights min
                                            • Child friendly
                                            • Air conditioning
                                            • Pet friendly

                                            from £104 / night

                                            £725 / week

                                            Book View

                                            from £104 / night

                                            (28) Excellent 

                                              33

                                              Cortona holiday apartment rental

                                              Province of Arezzo / Cortona

                                              1 4 4 nights min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 4 nights min
                                              • Child friendly
                                              “A great, beautiful, convenient stay in Cortona” This was our favorite place we stayed during a month in Italy. Vanna is so wonderfully gracious and friendly. The whole town of Cortona is like a medieval/renaissance fairy tale. There is plenty to do just within walking distance of this beautiful apartment. We did not have a car, but spent an incredible leisurely week as pedestrians in the area. Can't wait to return, and will definitely stay here again!

                                              from £96 / night

                                              £523 - £882 / week

                                              Book View

                                              from £96 / night

                                              (1) Excellent 

                                                18

                                                Cortona holiday b&b rental

                                                Province of Arezzo / Cortona

                                                11 20 2 nights min

                                                • 11 bedrooms
                                                • sleeps 20
                                                • 2 nights min
                                                • Swimming pool
                                                • Suitable for children age 5+
                                                • Air conditioning

                                                from £794 / night

                                                £4,962 / week

                                                Book View

                                                from £794 / night

                                                (10) Excellent 

                                                  18

                                                  Holiday apartment in Cortona

                                                  Province of Arezzo / Cortona

                                                  1 3 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • min stay varies

                                                  from £65 / night

                                                  £397 - £477 / week

                                                  Book View

                                                  from £65 / night

                                                    26

                                                    Holiday farmhouse with golf nearby in Fratticciola

                                                    Cortona / Fratticciola

                                                    13 29 3 nights min

                                                    • 13 bedrooms
                                                    • sleeps 29
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Air conditioning
                                                    • Private garden

                                                    from £973 / night

                                                    £6,807 / week

                                                    Book View

                                                    from £973 / night

                                                    (40) Excellent 

                                                    Certificate of Excellence

                                                      16

                                                      Cortona holiday home rental

                                                      Province of Arezzo / Cortona

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Nearest beach 150 km
                                                      • Child friendly
                                                      • Pet friendly

                                                      Certificate of Excellence

                                                      from £80 / night

                                                      £427 - £804 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 2 minutes

                                                      from £80 / night

                                                      (2) Very Good 

                                                        14

                                                        Montanare holiday farmhouse rental

                                                        Cortona / Montanare

                                                        6 16 2 nights min

                                                        • 6 bedrooms
                                                        • sleeps 16
                                                        • 2 nights min
                                                        • Child friendly
                                                        • Ask about pets
                                                        • Private garden

                                                        from £75 / night

                                                        £447 - £2,392 / week

                                                        Book View

                                                        from £75 / night

                                                        (1) Excellent 

                                                          42

                                                          Holiday cottage rental

                                                          Province of Arezzo / Cortona

                                                          3 6 3 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 3 nights min
                                                          • Swimming pool
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £128 / night

                                                          £896 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 1 minutes

                                                          from £128 / night

                                                            10

                                                            Cortona holiday apartment rental

                                                            Province of Arezzo / Cortona

                                                            1 3 7 nights min

                                                            • 1 bedroom
                                                            • sleeps 3
                                                            • 7 nights min
                                                            • Nearest beach 140 km
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £59 / night

                                                            £408 - £685 / week

                                                            Enquire View

                                                            from £59 / night

                                                              16

                                                              Cortona holiday apartment rental

                                                              Province of Arezzo / Cortona

                                                              2 4 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 6 km
                                                              • Suitable for children age 5+

                                                              from £82 / night

                                                              £573 / week

                                                              Book View

                                                              from £82 / night

                                                              (2) Excellent 

                                                                30

                                                                Holiday villa in Cortona

                                                                Province of Arezzo / Cortona

                                                                6 14 min stay varies

                                                                • 6 bedrooms
                                                                • sleeps 14
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £343 / night

                                                                £2,770 - £3,727 / week

                                                                Book View

                                                                from £343 / night

                                                                (2) Excellent 

                                                                  27

                                                                  Holiday lodge in Cortona

                                                                  Province of Arezzo / Cortona

                                                                  1 4 min stay varies

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • min stay varies
                                                                  • Nearest beach 0 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £79 / night

                                                                  £546 - £645 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 50 minutes

                                                                  from £79 / night

                                                                    35

                                                                    Holiday apartment in Cortona

                                                                    Province of Arezzo / Cortona

                                                                    1 2 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 3 nights min

                                                                    from £100 / night

                                                                    £695 / week

                                                                    Book View

                                                                    from £100 / night

                                                                      29

                                                                      Cottage rental in Pietraia with swimming pool

                                                                      Cortona / Pietraia

                                                                      2 4 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £121 / night

                                                                      £844 - £1,985 / week

                                                                      Book View

                                                                      from £121 / night

                                                                        27

                                                                        Cortona holiday lodge rental

                                                                        Province of Arezzo / Cortona

                                                                        1 4 min stay varies

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Nearest beach 0 km
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £79 / night

                                                                        £447 - £645 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 50 minutes

                                                                        from £79 / night

                                                                        (3) Excellent 

                                                                          26

                                                                          Holiday farmhouse with swimming pool in Farinaio

                                                                          Cortona / Farinaio

                                                                          4 9 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 9
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Private garden

                                                                          from £149 / night

                                                                          £1,092 - £1,191 / week

                                                                          Book View

                                                                          from £149 / night

                                                                          (7) Excellent 

                                                                            72

                                                                            Holiday home with swimming pool in Cortona

                                                                            Province of Arezzo / Cortona

                                                                            2 5 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 10 km
                                                                            • Swimming pool

                                                                            from £269 / night

                                                                            £1,884 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 3 hours 38 minutes

                                                                            from £269 / night

                                                                              26

                                                                              Cortona holiday apartment rental

                                                                              Province of Arezzo / Cortona

                                                                              2 6 3 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 3 nights min
                                                                              • Child friendly

                                                                              from £119 / night

                                                                              £837 - £985 / week

                                                                              Book View

                                                                              from £119 / night

                                                                              (3) Excellent 

                                                                                53

                                                                                Cortona holiday apartment rental

                                                                                Province of Arezzo / Cortona

                                                                                3 6 4 nights min

                                                                                • 3 bedrooms
                                                                                • sleeps 6
                                                                                • 4 nights min
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £139 / night

                                                                                £794 - £1,330 / week

                                                                                Book View

                                                                                from £139 / night

                                                                                (1) Excellent 

                                                                                  8

                                                                                  Home rental in Cortona with shared pool

                                                                                  Province of Arezzo / Cortona

                                                                                  3 6 4 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 4 nights min
                                                                                  • Beach / lakeside relaxation
                                                                                  • Nearest beach 80 km
                                                                                  • Swimming pool

                                                                                  from £328 / night

                                                                                  £2,283 / week

                                                                                  Book View

                                                                                  from £328 / night

                                                                                  Top Destination reviews

                                                                                  Casa del Balestriere In Centro Storico
                                                                                  Quiet spacious apartment

                                                                                  Wonderful base for a stay in Cortona. Two-floor one-bed apartment with lots of space, two bathrooms and a kitchen. Really well appointed with everything you need. It's a short stroll downhill into the centre of Cortona (steep walk back but only 5 mins). Just far enough away to be quiet despite festivities and celebrations in the centre. Host was so welcoming, collecting us from nearby carmucia train station and a delicious home made fruit tart. Would highly recommend.see more
                                                                                  Agriturismo Henni pool sauna jacuzzi panoramicview
                                                                                  Wonderful Villa with amazing views

                                                                                  A spacious comfortable villa equipped to a high standard that can easily accommodate 3 families with children. Garden/pool/pool house makes good use of the spacious garden with an outdoor dining/lounge area in the centre. Good service with the pool and hot tub cleaned on a regular basis throughout the week. Valentina helped to organise an evening with Christina who cooked wonderful authentic Toscany cuisine for both kids and grown ups, amazing! Wonderful views with Montepulciano in the horizon.see more
                                                                                  Holiday Villa in Cortona
                                                                                  Stunning villa, gracious owner

                                                                                  A group of 10 of us arrived for a week's stay in late July. The villa with 5 double en-suite bedrooms (all air conditioned) is immaculate. The lounge area and dining room are lovely but unused during our stay. The terrace is well situated and ideal for shade with transparent curtains for protection from occasional rain. Kitchen is small but adequate with plenty of crockery/cutlery for 10+ plus a dishwasher and coffee machine. There is a utility room with washing machine, tumble dryer plus games for outside The pool is lovely with enough sun beds for everyone and 6/8 parasols There is also a one bedroom annexe - again with aircon. This was ideal for a young couple in our party with a young baby. Therefore 6 doubles in total. On arrival a magnificent buffet was laid on the dining table which was really thoughtful - the following day was a Sunday and the villa is remote - many of our party were arriving late evening In all I would recommend the villa to anyone; you need a car as it is some distance from Cortona and the supermarket is downhill from there but the views are amazing and it's very peaceful. Grazia is a gracious host - she was so helpful - a very lovely lady. Please do not hesitate to book this villa - you won't be disappointedsee more
                                                                                  Villa il Giuggiolo - Azienda Fontelunga
                                                                                  Cosy and spacious villa in quiet idyllic location

                                                                                  Michele is a wonderful host. The villa is charming and very big. Its old fashioned and thats part of the charm. 5mins drive from cortona and with access to a lovely pool. Just idyllic and excellent value for money! … see more
                                                                                  Holiday house-the House Cells-
                                                                                  The Owner

                                                                                  Mauro, The owner was excellent to deal with. Even though we had to cancel, he went to lengths to be sure I was refunded my deposit. We look forward to staying at this charming Farm House next spring. Thank you Mauro! Chao!! ~Darlene M. … see more
                                                                                  To Stones
                                                                                  A ‘gem’ in Cortona

                                                                                  Alle Pietre would without doubt, be the best holiday home we have stayed in over the past ten years. From the very beginning, the communication from Ester, the owner, was excellent and the welcome from both Ester and her husband Giovanni was wonderful - like meeting old friends, they were warm and genuinely wanted us to have a fabulous time - we did! The house is in the most perfect position by the wall looking into the valley below - watching the sunset from this spot was absolutely breath taking. The house has been recently renovated from top to bottom and to a very high standard, it is furnished with exquisite antique style furniture. The kitchen is exceptionally well equipped and bed linen and towels of a very high standard. Everything worked and Ester was just a txt message away if help was required. We absolutely loved our two weeks at Alle Pietre and are hoping to return next year. Thank you Ester and Giovanni for everything.see more

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