Villas in Castiglion Fiorentino and Houses – Holiday Lettings - Holiday Rentals Castiglion Fiorentino

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3,953 Holiday homes

    8

    Holiday farmhouse with shared pool in Castiglion Fiorentino

    Province of Arezzo / Castiglion Fiorentino

    13 5 2 nights min

    • 13 bedrooms
    • sleeps 5
    • 2 nights min
    • Swimming pool
    • Child friendly
    • Ask about pets

    from £61 / night

    £383 / week

    Book View

    from £61 / night

    (13) Excellent 

    Certificate of Excellence

      22

      Cottage accommodation in Pieve di Chio with swimming pool

      Castiglion Fiorentino / Pieve di Chio

      2 6 7 nights min

      • 2 bedrooms
      • sleeps 6
      • 7 nights min
      • Swimming pool
      • Child friendly
      • Pet friendly

      Certificate of Excellence

      from £142 / night

      £990 / week

      Book View

      Responds fast!
      avg. 1 hour 2 minutes

      from £142 / night

      (8) Excellent 

        12

        Holiday home with swimming pool in Castiglion Fiorentino

        Province of Arezzo / Castiglion Fiorentino

        6 13 7 nights min

        • 6 bedrooms
        • sleeps 13
        • 7 nights min
        • Swimming pool
        • Child friendly
        • Ask about pets

        from £504 / night

        £3,525 / week

        Book View

        from £504 / night

          33

          Holiday apartment with shared pool in Castiglion Fiorentino

          Province of Arezzo / Castiglion Fiorentino

          3 8 1 night min

          • 3 bedrooms
          • sleeps 8
          • 1 night min
          • Nearest beach 156 km
          • Swimming pool
          • Child friendly

          from £202 / night

          £1,410 / week

          Book View

          from £202 / night

            44

            Villa rental in Castiglion Fiorentino

            Province of Arezzo / Castiglion Fiorentino

            4 10 min stay varies

            • 4 bedrooms
            • sleeps 10
            • min stay varies
            • Child friendly
            • Pet friendly

            from £303 / night

            £1,410 / week

            Book View

            from £303 / night

              16

              Castiglion Fiorentino holiday home rental

              Province of Arezzo / Castiglion Fiorentino

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Child friendly
              • Pet friendly

              from £51 / night

              £353 / week

              Book View

              from £51 / night

              (4) Excellent 

                20

                Holiday apartment rental

                Province of Arezzo / Castiglion Fiorentino

                2 6 5 nights min

                • 2 bedrooms
                • sleeps 6
                • 5 nights min
                • Child friendly
                • Air conditioning
                • Pet friendly

                from £91 / night

                £579 - £720 / week

                Book View

                from £91 / night

                (5) Excellent 

                  52

                  Holiday farmhouse in Brolio

                  Castiglion Fiorentino / Brolio

                  4 8 min stay varies

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

                  from £172 / night

                  £987 - £1,561 / week

                  Book View

                  from £172 / night

                    11

                    Holiday townhouse with shared pool in Orzale

                    Castiglion Fiorentino / Orzale

                    2 5 3 nights min

                    • 2 bedrooms
                    • sleeps 5
                    • 3 nights min
                    • Swimming pool
                    • Child friendly
                    • Ask about pets

                    from £182 / night

                    £856 / week

                    Book View

                    from £182 / night

                      14

                      Holiday condo with shared pool in Montecchio Vesponi

                      Castiglion Fiorentino / Montecchio Vesponi

                      2 5 2 nights min

                      • 2 bedrooms
                      • sleeps 5
                      • 2 nights min
                      • Swimming pool
                      • Child friendly
                      • Pet friendly

                      from £69 / night

                      £480 / week

                      Book View

                      from £69 / night

                        21

                        Holiday apartment with shared pool in Castiglion Fiorentino

                        Province of Arezzo / Castiglion Fiorentino

                        2 5 3 nights min

                        • 2 bedrooms
                        • sleeps 5
                        • 3 nights min
                        • Swimming pool
                        • Child friendly

                        from £182 / night

                        £907 / week

                        Book View

                        Responds fast!
                        avg. 3 hours 20 minutes

                        from £182 / night

                          25

                          Holiday villa with swimming pool in Castiglion Fiorentino

                          Province of Arezzo / Castiglion Fiorentino

                          4 8 min stay varies

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

                          from £403 / night

                          £1,481 - £3,022 / week

                          Book View

                          from £403 / night

                            58

                            Holiday villa with indoor pool in Brolio

                            Castiglion Fiorentino / Brolio

                            9 18 min stay varies

                            • 9 bedrooms
                            • sleeps 18
                            • min stay varies
                            • Nearest beach 125 km
                            • Swimming pool
                            • Child friendly

                            from £599 / night

                            £2,991 - £6,465 / week

                            Enquire View

                            from £599 / night

                            (2) Excellent 

                              14

                              Holiday b&b in Castiglion Fiorentino

                              Province of Arezzo / Castiglion Fiorentino

                              1 2 2 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 2 nights min
                              • Ask about pets

                              from £91 / night

                              £554 / week

                              Book View

                              from £91 / night

                                26

                                Home rental in Castiglion Fiorentino with swimming pool

                                Province of Arezzo / Castiglion Fiorentino

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Swimming pool
                                • Child friendly
                                • Pet friendly

                                from £202 / night

                                £1,410 / week

                                Book View

                                from £202 / night

                                (3) Excellent 

                                  14

                                  Holiday villa in Castiglion Fiorentino

                                  Province of Arezzo / Castiglion Fiorentino

                                  3 6 7 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Child friendly
                                  • Ask about pets
                                  • Private garden

                                  from £317 / night

                                  £2,216 / week

                                  Book View

                                  from £317 / night

                                    6

                                    Castiglion Fiorentino holiday apartment rental

                                    Province of Arezzo / Castiglion Fiorentino

                                    2 6 1 night min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 1 night min
                                    • Child friendly
                                    • Pet friendly

                                    from £121 / night

                                    £705 / week

                                    Book View

                                    from £121 / night

                                      8

                                      Holiday b&b in Castiglion Fiorentino

                                      Province of Arezzo / Castiglion Fiorentino

                                      1 3 1 night min

                                      • 1 bedroom
                                      • sleeps 3
                                      • 1 night min
                                      • Swimming pool
                                      • Child friendly
                                      • Private garden

                                      from £81 / night

                                      £514 / week

                                      Book View

                                      from £81 / night

                                        28

                                        Villa rental in Castiglion Fiorentino with swimming pool

                                        Province of Arezzo / Castiglion Fiorentino

                                        6 12 7 nights min

                                        • 6 bedrooms
                                        • sleeps 12
                                        • 7 nights min
                                        • Swimming pool
                                        • Ask owner if suitable for children

                                        from £484 / night

                                        £3,324 / week

                                        Book View

                                        Responds fast!
                                        avg. 3 hours 20 minutes

                                        from £484 / night

                                          33

                                          Holiday villa rental

                                          Province of Arezzo / Castiglion Fiorentino

                                          3 6 7 nights min

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

                                          from £288 / night

                                          £2,015 - £3,324 / week

                                          Book View

                                          from £288 / night

                                            23

                                            Holiday villa rental

                                            Castiglion Fiorentino / Pieve di Chio

                                            5 14 4 nights min

                                            • 5 bedrooms
                                            • sleeps 14
                                            • 4 nights min
                                            • Child friendly
                                            • Pet friendly

                                            from £137 / night

                                            £957 / week

                                            Book View

                                            Responds fast!
                                            avg. 18 minutes

                                            from £137 / night

                                              4

                                              Holiday apartment rental

                                              Province of Arezzo / Castiglion Fiorentino

                                              1 4 2 nights min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 2 nights min
                                              • Child friendly
                                              • Pet friendly
                                              • Private garden

                                              from £71 / night

                                              £474 / week

                                              Book View

                                              from £71 / night

                                              (1) Excellent 

                                                14

                                                Holiday apartment in Castiglion Fiorentino

                                                Province of Arezzo / Castiglion Fiorentino

                                                2 5 1 night min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 1 night min
                                                • Child friendly
                                                • Pet friendly

                                                from £77 / night

                                                £536 / week

                                                Book View

                                                from £77 / night

                                                (4) Excellent 

                                                  24

                                                  Holiday home with swimming pool in Castiglion Fiorentino

                                                  Province of Arezzo / Castiglion Fiorentino

                                                  3 8 min stay varies

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

                                                  from £222 / night

                                                  £1,551 / week

                                                  Book View

                                                  from £222 / night

                                                  (1) Excellent 

                                                    23

                                                    Holiday apartment with shared pool in Castiglion Fiorentino

                                                    Province of Arezzo / Castiglion Fiorentino

                                                    3 8 7 nights min

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • 7 nights min
                                                    • Nearest beach 156 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £202 / night

                                                    £1,410 / week

                                                    Book View

                                                    from £202 / night

                                                      50

                                                      Holiday farmhouse letting

                                                      Province of Arezzo / Castiglion Fiorentino

                                                      2 6 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Pet friendly

                                                      from £124 / night

                                                      £868 - £1,904 / week

                                                      Book View

                                                      from £124 / night

                                                        15

                                                        Holiday cottage with shared pool in Castiglion Fiorentino

                                                        Province of Arezzo / Castiglion Fiorentino

                                                        4 10 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child friendly
                                                        • Pet friendly

                                                        from £216 / night

                                                        £1,511 / week

                                                        Book View

                                                        from £216 / night

                                                          12

                                                          Holiday villa accommodation

                                                          Province of Arezzo / Castiglion Fiorentino

                                                          2 6 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 6
                                                          • 1 night min
                                                          • Child friendly
                                                          • Ask about pets

                                                          from £81 / night

                                                          £353 / week

                                                          Book View

                                                          from £81 / night

                                                          (19) Excellent 

                                                            49

                                                            Holiday villa with swimming pool in Castiglion Fiorentino

                                                            Province of Arezzo / Castiglion Fiorentino

                                                            4 8 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £308 / night

                                                            £1,461 - £3,304 / week

                                                            Book View

                                                            from £308 / night

                                                            (1) Excellent 

                                                              13

                                                              Castiglion Fiorentino holiday apartment rental

                                                              Province of Arezzo / Castiglion Fiorentino

                                                              2 4 2 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 2 nights min
                                                              • Child friendly

                                                              from £71 / night

                                                              £494 / week

                                                              Book View

                                                              from £71 / night

                                                                49

                                                                Castiglion Fiorentino holiday villa rental

                                                                Province of Arezzo / Castiglion Fiorentino

                                                                7 14 7 nights min

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

                                                                from £274 / night

                                                                £1,914 - £4,532 / week

                                                                Book View

                                                                from £274 / night

                                                                (2) Excellent 

                                                                  38

                                                                  Holiday farmhouse in Castiglion Fiorentino

                                                                  Province of Arezzo / Castiglion Fiorentino

                                                                  4 9 min stay varies

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

                                                                  from £182 / night

                                                                  £1,269 - £2,397 / week

                                                                  Book View

                                                                  from £182 / night

                                                                  (2) Excellent 

                                                                    17

                                                                    Farmhouse rental in Castiglion Fiorentino with shared pool

                                                                    Province of Arezzo / Castiglion Fiorentino

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £101 / night

                                                                    £705 / week

                                                                    Book View

                                                                    from £101 / night

                                                                    (4) Excellent 

                                                                      59

                                                                      Holiday villa with swimming pool in Castiglion Fiorentino

                                                                      Province of Arezzo / Castiglion Fiorentino

                                                                      7 18 5 nights min

                                                                      • 7 bedrooms
                                                                      • sleeps 18
                                                                      • 5 nights min
                                                                      • Nearest beach 160 km
                                                                      • Swimming pool
                                                                      • Child friendly

                                                                      from £328 / night

                                                                      £2,292 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 58 minutes

                                                                      from £328 / night

                                                                      (1) Excellent 

                                                                        30

                                                                        Holiday apartment in Castiglion Fiorentino

                                                                        Province of Arezzo / Castiglion Fiorentino

                                                                        3 7 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 7
                                                                        • min stay varies
                                                                        • Child friendly
                                                                        • Pet friendly

                                                                        from £101 / night

                                                                        £504 - £705 / week

                                                                        Book View

                                                                        from £101 / night

                                                                          18

                                                                          Holiday farmhouse in Castiglion Fiorentino

                                                                          Province of Arezzo / Castiglion Fiorentino

                                                                          1 4 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 3 nights min
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £126 / night

                                                                          £882 / week

                                                                          Book View

                                                                          from £126 / night

                                                                          (1) Excellent 

                                                                            19

                                                                            Holiday farmhouse in Castiglion Fiorentino

                                                                            Province of Arezzo / Castiglion Fiorentino

                                                                            1 3 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 3
                                                                            • 3 nights min
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £116 / night

                                                                            £811 / week

                                                                            Book View

                                                                            from £116 / night

                                                                              28

                                                                              Home rental in Castiglion Fiorentino with swimming pool

                                                                              Province of Arezzo / Castiglion Fiorentino

                                                                              5 9 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 9
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £153 / night

                                                                              £1,073 - £2,242 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 36 minutes

                                                                              from £153 / night

                                                                                45

                                                                                Holiday villa in Castiglion Fiorentino

                                                                                Province of Arezzo / Castiglion Fiorentino

                                                                                4 8 7 nights min

                                                                                • 4 bedrooms
                                                                                • sleeps 8
                                                                                • 7 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Private garden

                                                                                from £360 / night

                                                                                £2,518 - £4,281 / week

                                                                                Book View

                                                                                from £360 / night

                                                                                  20

                                                                                  Castiglion Fiorentino holiday apartment rental

                                                                                  Province of Arezzo / Castiglion Fiorentino

                                                                                  2 3 3 nights min

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

                                                                                  from £121 / night

                                                                                  £454 / week

                                                                                  Book View

                                                                                  from £121 / night

                                                                                  Top Destination reviews

                                                                                  TUSCANY VILLA PRINCIPE 8 prsns
                                                                                  A real gem in Tuscany

                                                                                  The villa is situated near to Castiglion Fiorentino which is a delightful spot in the heart of Tuscany. Florence, Siena and the vineyards of Chianti and Montepulciano are are accessible. Castiglion is well served by a train service to Florence and Rome if you do not fancy driving. The villa has a fantastic location at 600 metres up a hill pass. Being far enough away from any kind of hamlet, it gives a real sense of peace and tranquility. The views from the garden and pool areas provide breathtaking vistas of the Tuscan countryside. At night, relatively unpolluted by lights, the stars truly fill every part of the sky. The villa is spacious, tastefully and authentically furnished and provides absolutely everything you need. The bedrooms were very comfortable and the kitchen facilities comprehensive. It was a real joy to make great food(sometimes at the barbecue) and eat with family on the beautiful terrace. The host, Daniele, is a real gentleman and was always available to offer advice on how to best to use his home or enjoy the region. The villa was utterly ideal for our family of 5 adults and 4 children and we would recommend it wholeheartedly. Thank you Daniele for being such a great host. We hope to see you again one day!see more
                                                                                  Villa Margarita, Garden Apartment with lovely Pool
                                                                                  Amazing villa, peaceful with stunning views. Perfect location!

                                                                                  We stayed at this villa last Summer. Despite some confusion over our arrival day the owners and family ensured the villa was prepared for us before we settled in. I believe we were the first people to stay in the villa and it was perfect for our family. The bedrooms were beautifully furnished and the views were truly fabulous. We were able to eat al fresco on the balcony or terrace. The pool and surrounding area were just stunning - perfect for a family. The location and vista were perfect. We had a hire car (required due to the location) and were able to visit local village and towns. We enjoyed Florence and Sienna for day trips. The town of Cortona was very special. All in all a great villa with accommodating owners who tried very hard to make our stay perfect.see more
                                                                                  Villa Il Ceriolo
                                                                                  Charming, comfortable country villa, conveniently located.

                                                                                  Charming villa, comfortably accommodates 12 adults. Can be divided into 3 separate 2-bedroom apartments, each with its own kitchen/dining/bath and living area, or rented as one for use by a group. Centrally located in the heart of Tuscany, between Cortona and Arezzo. Easy day trips to surrounding small and large towns. The Villa is in the center of its own orchard and grape vines, with lovely outside dining/gathering spaces, and a swimming pool. The owner, Harriet Sculley, provided directions to local and area restaurants and sites of interest. Also guided us to a couple of terrific cooking classes.see more
                                                                                  Cottage maltilde - Casa Matilde. Family Home for 3-4 guests. Private Pool.
                                                                                  Peace and tranquility

                                                                                  We had a great time, the pool was most welcome and the peace and tranquility much appreciated (only noise was the chickens next door!). It is quite remote but the stars were great and we even saw a porcupine. … see more
                                                                                  Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a  small Tuscan borgo
                                                                                  Not to be missed

                                                                                  This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored are within easy reach. There is plenty to see and do or you can just relax and enjoy the stillness as you lounge by the pool. A good selection "of delightful restaurants around in which to sample wonderful Italian food and wines. Looking forward to revisiting the delights of Tuscanny from this well situated holiday home.see more
                                                                                  Borgo Tranquilitta - IL SOLE - Family Cottages in Tuscany with pool.
                                                                                  Looking forward to next time

                                                                                  We thoroughly enjoyed our holiday at Borgo Tranquillita. It is the perfect place to stay whether you use it as a base for travelling the eastern part of Tuscany or just for a relaxing time at the top of picturesque hill. Lots of space around the three cottages, the perfect place for our dog. lots of privacy for ourselves. The cottage is clean and comfortable, the kitchen has got everything it needs - basics, no fuss - , the Wi-Fi works. The pool is just a few steps away from the cottage and we spent a lot of time just there catching up on some books and relaxing. But we also made a few day trips to places like Cortona, Arezzo, Gubbio and Florence which can also easily be reached by car. Taking the train to Florence is more comfortable though. There are also a couple of nice restaurants in Castiglion Fiorentino - namely Il Passagio and Pietro are well worth a visit. Thanks to the owner and Terry in particular who were very friendly and obliging. We felt at home from day 1. This a the perfect place to unwind and we wouldn´t hesitate to return, we loved it! Until next time...see more
                                                                                  Borgo Tranquilitta - LA LUNA
                                                                                  Rustic charm and a five star pool with a breathtaking view

                                                                                  This was indeed a haven of peace high up in the hills with a lovely view across the valley to the hills on the other side. The well appointed cottages make you feel you are part of the local landscape and the pool and its surroundings are delightfully luxurious. There are plenty of interesting places to see nearby, including Castiglione Fiorentino and Cortana.see more
                                                                                  Tuscany cottage near Castiglion Fiorentino, with Private Pool, BBQ, & Parking
                                                                                  The Trip of a Lifetime!!

                                                                                  This was a beautiful experience! The house was out in the country but not too far away from all of the activities and conveniences. It was beautiful at night! A million stars and so very quiet! It was up on a hill so the view was lovely; vineyards and orchards just like a postcard. The whole house was renovated. The kitchen has all of the best and most up to date appliances. Both of the bathrooms have all new fixtures and were spotlessly clean. The linens that were supplied were of the highest quality. Since this is an old country house there is no air conditioning but the owner supplies fans which work just fine to cool the hot August summer days and nights. The pool is beautiful and they even supplied beach towels! The pool and patio area included a little pool house with a sink. There is a grill and nice outdoor furniture which we enjoyed on our "stay at home" day of relaxation. The whole area is just breathtaking. We rented a car and the driving was very easy and safe in this area. Not a lot of traffic. We drove all along the main highway and visited all of the beautiful old cities. All of them were less than a 1/2 hour drive from the house. The property managers are very accessible, spoke very good English and were able to advise us on places to see. We always felt very comfortable. I could go on and on and I just cannot think of anything negative to say about it!!see more
                                                                                  Brolio Quinto - Typical Farmhouse in tuscan countryside near Cortona
                                                                                  Tuscan escape

                                                                                  We stayed her last August with two families It was the best holiday we've had so far, the place is amazing and very central for families who like to explore. Giovanna was really helpful and even gave us a lift into Cortona one evening. The dogs are all lovely also and the children enjoyed playing with them. Would really recommend A+see more

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