Cottages in Windermere and Log cabins - Holiday Lettings - Holiday Rentals Windermere

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21,455 Holiday homes

    25

    Windermere holiday home let

    Central Florida / Windermere

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Swimming pool
    • Ask owner if suitable for children

    from £770 / night

    £5,389 / week

    Enquire View

    from £770 / night

      31

      Holiday townhouse with shared pool in Windermere

      Central Florida / Windermere

      4 8 5 nights min

      • 4 bedrooms
      • sleeps 8
      • 5 nights min
      • Swimming pool
      • Ask owner if suitable for children
      • Air conditioning

      from £99 / night

      £691 / week

      Book View

      Responds fast!
      avg. 3 hours 58 minutes

      from £99 / night

        49

        Windermere holiday guest house rental

        Central Florida / Windermere

        2 4 1 night min

        • 2 bedrooms
        • sleeps 4
        • 1 night min

        from £89 / night

        £661 - £847 / week

        Book View

        from £89 / night

          31

          Holiday townhouse with shared pool in Windermere

          Central Florida / Windermere

          4 8 5 nights min

          • 4 bedrooms
          • sleeps 8
          • 5 nights min
          • Swimming pool
          • Ask owner if suitable for children
          • Air conditioning

          from £99 / night

          £691 / week

          Book View

          Responds fast!
          avg. 2 hours 22 minutes

          from £99 / night

            16

            Windermere holiday condo rental

            Central Florida / Windermere

            1 4 2 nights min

            • 1 bedroom
            • sleeps 4
            • 2 nights min
            • Swimming pool
            • Child friendly
            • Air conditioning

            from £77 / night

            £537 / week

            Book View

            Responds fast!
            avg. 1 hour 37 minutes

            from £77 / night

              18

              Holiday home in Windermere

              Central Florida / Windermere

              4 8 5 nights min

              • 4 bedrooms
              • sleeps 8
              • 5 nights min
              • Swimming pool
              • Child friendly
              • Air conditioning

              from £83 / night

              £577 / week

              Enquire View

              from £83 / night

                7

                Holiday home in Windermere

                Central Florida / Windermere

                2 6 1 night min

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

                from £192 / night

                £1,338 / week

                Book View

                from £192 / night

                  13

                  Holiday home in Windermere

                  Central Florida / Windermere

                  2 4 1 night min

                  • 2 bedrooms
                  • sleeps 4
                  • 1 night min
                  • Child friendly

                  from £182 / night

                  £1,275 / week

                  Book View

                  from £182 / night

                    24

                    Condo rental in Windermere

                    Central Florida / Windermere

                    1 4 2 nights min

                    • 1 bedroom
                    • sleeps 4
                    • 2 nights min
                    • Swimming pool
                    • Child friendly
                    • Air conditioning

                    from £62 / night

                    £432 / week

                    Book View

                    Responds fast!
                    avg. 19 minutes

                    from £62 / night

                      13

                      Holiday home with shared pool in Windermere

                      Central Florida / Windermere

                      3 6 2 nights min

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

                      from £309 / night

                      £2,644 / week

                      Book View

                      from £309 / night

                        10

                        Holiday home in Windermere

                        Central Florida / Windermere

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Child friendly

                        from £126 / night

                        £653 - £1,143 / week

                        Book View

                        from £126 / night

                          16

                          Windermere holiday condo rental

                          Central Florida / Windermere

                          1 6 2 nights min

                          • 1 bedroom
                          • sleeps 6
                          • 2 nights min
                          • Swimming pool
                          • Child friendly
                          • Air conditioning

                          from £96 / night

                          £673 / week

                          Book View

                          Responds fast!
                          avg. 1 hour 37 minutes

                          from £96 / night

                            31

                            Holiday townhouse in Windermere

                            Central Florida / Windermere

                            4 8 5 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 5 nights min
                            • Swimming pool
                            • Child friendly
                            • Air conditioning

                            from £103 / night

                            £716 / week

                            Book View

                            Responds fast!
                            avg. 1 hour 59 minutes

                            from £103 / night

                              52

                              Holiday villa with swimming pool in Windermere

                              Central Florida / Windermere

                              6 14 5 nights min

                              • 6 bedrooms
                              • sleeps 14
                              • 5 nights min
                              • Swimming pool
                              • Ask owner if suitable for children
                              • Air conditioning

                              from £537 / night

                              £3,758 / week

                              Book View

                              Responds fast!
                              avg. 3 hours 58 minutes

                              from £537 / night

                                15

                                Holiday condo in Windermere

                                Central Florida / Windermere

                                1 4 min stay varies

                                • 1 bedroom
                                • sleeps 4
                                • min stay varies
                                • Swimming pool
                                • Child friendly
                                • Air conditioning

                                from £70 / night

                                £488 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 37 minutes

                                from £70 / night

                                  7

                                  Holiday townhouse rental

                                  Central Florida / Windermere

                                  4 8 5 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 5 nights min
                                  • Swimming pool
                                  • Ask owner if suitable for children
                                  • Air conditioning

                                  from £148 / night

                                  £1,037 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 16 minutes

                                  from £148 / night

                                    15

                                    Holiday condo in Windermere

                                    Central Florida / Windermere

                                    1 4 2 nights min

                                    • 1 bedroom
                                    • sleeps 4
                                    • 2 nights min
                                    • Swimming pool
                                    • Child friendly
                                    • Air conditioning

                                    from £118 / night

                                    £821 / week

                                    Book View

                                    Responds fast!
                                    avg. 1 hour 37 minutes

                                    from £118 / night

                                      13

                                      Holiday condo with shared pool in Windermere

                                      Central Florida / Windermere

                                      1 4 2 nights min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 2 nights min
                                      • Swimming pool
                                      • Child friendly
                                      • Air conditioning

                                      from £83 / night

                                      £580 / week

                                      Book View

                                      Responds fast!
                                      avg. 1 hour 37 minutes

                                      from £83 / night

                                        16

                                        Holiday condo with shared pool in Windermere

                                        Central Florida / Windermere

                                        2 6 2 nights min

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

                                        from £91 / night

                                        £636 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 37 minutes

                                        from £91 / night

                                        Great rentals within 20 miles that match your search

                                        Distance approx 12.08 miles from Windermere

                                          25

                                          Holiday apartment in Four Corners

                                          Central Florida / Four Corners

                                          2 8 6 nights min

                                          • 2 bedrooms
                                          • sleeps 8
                                          • 6 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £201 / night

                                          £1,403 / week

                                          Book View

                                          from £201 / night

                                          Distance approx 13.18 miles from Windermere

                                            7

                                            Old Town holiday apartment rental

                                            Florida / Old Town

                                            3 6 3 nights min

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

                                            from £87 / night

                                            £606 / week

                                            Book View

                                            from £87 / night

                                            Distance approx 17.5 miles from Windermere

                                              16

                                              Holiday villa in ChampionsGate

                                              Central Florida / ChampionsGate

                                              5 10 7 nights min

                                              • 5 bedrooms
                                              • sleeps 10
                                              • 7 nights min
                                              • Swimming pool
                                              • Air conditioning

                                              from £254 / night

                                              £1,772 / week

                                              Book View

                                              from £254 / night

                                              Distance approx 15.88 miles from Windermere

                                              (9) Average 

                                                15

                                                Home rental in Davenport with swimming pool

                                                Central Florida / Davenport

                                                5 10 2 nights min

                                                • 5 bedrooms
                                                • sleeps 10
                                                • 2 nights min
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £281 / night

                                                £1,963 / week

                                                Book View

                                                from £281 / night

                                                Distance approx 13.23 miles from Windermere

                                                (15) Excellent 

                                                  24

                                                  Kissimmee holiday villa rental

                                                  Kissimmee / Calabria, Orlando

                                                  5 10 min stay varies

                                                  • 5 bedrooms
                                                  • sleeps 10
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  from £219 / night

                                                  £1,533 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 43 minutes

                                                  from £219 / night

                                                  Distance approx 16.48 miles from Windermere

                                                    16

                                                    Holiday villa in Loughman

                                                    Central Florida / Loughman

                                                    5 10 7 nights min

                                                    • 5 bedrooms
                                                    • sleeps 10
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Air conditioning

                                                    from £233 / night

                                                    £1,625 / week

                                                    Book View

                                                    from £233 / night

                                                    Distance approx 12.77 miles from Windermere

                                                      24

                                                      Holiday home in Four Corners

                                                      Central Florida / Four Corners

                                                      6 12 min stay varies

                                                      • 6 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Child friendly

                                                      from £138 / night

                                                      £962 / week

                                                      Book View

                                                      from £138 / night

                                                      Distance approx 12.45 miles from Windermere

                                                        12

                                                        Holiday hotel apartment with golf nearby in Kissimmee

                                                        Central Florida / Kissimmee

                                                        1 4 7 nights min

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Child friendly

                                                        from £53 / night

                                                        £368 / week

                                                        Book View

                                                        from £53 / night

                                                        Distance approx 8.99 miles from Windermere

                                                          10

                                                          Holiday villa in Old Town

                                                          Florida / Old Town

                                                          2 8 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £176 / night

                                                          £1,227 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 42 minutes

                                                          from £176 / night

                                                          Distance approx 6.21 miles from Windermere Show on Map

                                                          (3) Average 

                                                            19

                                                            Holiday hotel apartment in Orlando

                                                            Central Florida / Orlando

                                                            2 8 6 nights min

                                                            • 2 bedrooms
                                                            • sleeps 8
                                                            • 6 nights min
                                                            • Beach / lakeside relaxation
                                                            • Swimming pool
                                                            • Child friendly

                                                            from £237 / night

                                                            £1,492 / week

                                                            Book View

                                                            from £237 / night

                                                            Distance approx 15.29 miles from Windermere

                                                            (17) Excellent 

                                                            Certificate of Excellence

                                                              27

                                                              Holiday townhouse in Orlando

                                                              Central Florida / Orlando

                                                              3 7 3 nights min

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

                                                              Certificate of Excellence

                                                              from £84 / night

                                                              £584 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 15 minutes

                                                              from £84 / night

                                                              Distance approx 19.44 miles from Windermere

                                                                20

                                                                Holiday home with swimming pool, golf nearby in Davenport

                                                                Central Florida / Davenport

                                                                6 12 6 nights min

                                                                • 6 bedrooms
                                                                • sleeps 12
                                                                • 6 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Car not necessary

                                                                from £344 / night

                                                                £2,404 / week

                                                                Book View

                                                                from £344 / night

                                                                Distance approx 7.63 miles from Windermere Show on Map

                                                                  19

                                                                  Holiday villa in Orlando

                                                                  Central Florida / Orlando

                                                                  3 8 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £770 / night

                                                                  £5,389 / week

                                                                  Book View

                                                                  from £770 / night

                                                                  Distance approx 17.74 miles from Windermere

                                                                    37

                                                                    Holiday villa with swimming pool, golf nearby in ChampionsGate

                                                                    Central Florida / ChampionsGate

                                                                    6 12 min stay varies

                                                                    • 6 bedrooms
                                                                    • sleeps 12
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £275 / night

                                                                    £1,923 / week

                                                                    Book View

                                                                    from £275 / night

                                                                    Distance approx 11.96 miles from Windermere

                                                                    (3) Average 

                                                                      15

                                                                      Orlando holiday home rental

                                                                      Central Florida / Orlando

                                                                      4 8 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £112 / night

                                                                      £779 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 41 minutes

                                                                      from £112 / night

                                                                      Distance approx 14.12 miles from Windermere

                                                                        15

                                                                        Four Corners holiday condo rental

                                                                        Central Florida / Four Corners

                                                                        3 6 5 nights min

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

                                                                        from £106 / night

                                                                        £703 / week

                                                                        Book View

                                                                        from £106 / night

                                                                        Distance approx 12.38 miles from Windermere

                                                                          36

                                                                          Holiday townhouse in Kissimmee

                                                                          Central Florida / Kissimmee

                                                                          3 8 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 8
                                                                          • 2 nights min
                                                                          • Child friendly
                                                                          • Air conditioning
                                                                          • Pet friendly

                                                                          from £79 / night

                                                                          £547 - £698 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 1 hour 17 minutes

                                                                          from £79 / night

                                                                          Distance approx 11.99 miles from Windermere

                                                                            16

                                                                            Orlando holiday apartment accommodation

                                                                            Central Florida / Orlando

                                                                            1 4 7 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £190 / night

                                                                            £1,325 / week

                                                                            Book View

                                                                            from £190 / night

                                                                            Distance approx 15.66 miles from Windermere

                                                                              16

                                                                              Holiday villa with swimming pool in Four Corners

                                                                              Central Florida / Four Corners

                                                                              4 8 7 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Air conditioning

                                                                              from £186 / night

                                                                              £1,297 / week

                                                                              Book View

                                                                              from £186 / night

                                                                              Distance approx 17.74 miles from Windermere

                                                                              (42) Excellent 

                                                                                22

                                                                                Davenport holiday villa rental

                                                                                Davenport / West Haven

                                                                                5 12 min stay varies

                                                                                • 5 bedrooms
                                                                                • sleeps 12
                                                                                • min stay varies
                                                                                • Beach / lakeside relaxation
                                                                                • Nearest beach 80 km
                                                                                • Swimming pool

                                                                                from £90 / night

                                                                                £495 - £875 / week

                                                                                Enquire View

                                                                                from £90 / night

                                                                                Distance approx 14.5 miles from Windermere

                                                                                  20

                                                                                  Villa rental in Reunion with swimming pool

                                                                                  Central Florida / Reunion

                                                                                  1 22 min stay varies

                                                                                  • 1 bedroom
                                                                                  • sleeps 22
                                                                                  • min stay varies
                                                                                  • Swimming pool
                                                                                  • Air conditioning

                                                                                  from £758 / night

                                                                                  £5,302 / week

                                                                                  Book View

                                                                                  from £758 / night

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