Holiday Houses in Winter Garden

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14,344 Holiday homes

    6

    Central Florida / Winter Garden

    4 8 3 nights min

    • 4 bedrooms
    • sleeps 8
    • 3 nights min
    • Child friendly

    from £113 / night

    £676 / week

    Book View

    from £113 / night

    (3) Excellent 

      25

      Central Florida / Winter Garden

      3 6 7 nights min

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

      from £63 / night

      £441 - £516 / week

      Book View

      Responds fast!
      avg. 1 hour 6 minutes

      from £63 / night

      (2) Excellent 

        16

        Central Florida / Winter Garden

        3 7 1 night min

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

        from £63 / night

        £513 - £702 / week

        Book View

        Responds fast!
        avg. 2 hours 55 minutes

        from £63 / night

        (19) Excellent 

        Certificate of Excellence

          31

          Central Florida / Winter Garden

          3 8 4 nights min

          • 3 bedrooms
          • sleeps 8
          • 4 nights min
          • Child friendly
          • Air conditioning

          Certificate of Excellence

          from £86 / night

          £458 - £493 / week

          Book View

          from £86 / night

          (1) Excellent 

            18

            Central Florida / Winter Garden

            3 8 3 nights min

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

            from £113 / night

            £715 / week

            Book View

            from £113 / night

            (2) Very Good 

              8

              Central Florida / Winter Garden

              3 8 5 nights min

              • 3 bedrooms
              • sleeps 8
              • 5 nights min
              • Child friendly
              • Air conditioning

              from £75 / night

              £487 / week

              Book View

              Responds fast!
              avg. 3 hours 13 minutes

              from £75 / night

                26

                Central Florida / Winter Garden

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Child friendly
                • Air conditioning

                from £90 / night

                £626 / week

                Book View

                Responds fast!
                avg. 30 minutes

                from £90 / night

                  9

                  Central Florida / Winter Garden

                  2 6 7 nights min

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

                  from £63 / night

                  £442 / week

                  Book View

                  from £63 / night

                    10

                    Central Florida / Winter Garden

                    1 4 7 nights min

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

                    from £55 / night

                    £384 / week

                    Book View

                    from £55 / night

                      10

                      Central Florida / Winter Garden

                      2 6 3 nights min

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

                      from £177 / night

                      £1,233 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 42 minutes

                      from £177 / night

                      Great rentals within 20 miles that match your search

                      Distance approx 28.56 km from Winter Garden

                        16

                        Central Florida / Four Corners

                        6 12 7 nights min

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

                        from £256 / night

                        £1,791 / week

                        Book View

                        from £256 / night

                        Distance approx 31.5 km from Winter Garden

                        (3) Excellent 

                          15

                          Davenport / The Manors North at Westridge

                          4 8 3 nights min

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

                          from £103 / night

                          £722 / week

                          Book View

                          Responds fast!
                          avg. 1 hour 36 minutes

                          from £103 / night

                          Distance approx 23.46 km from Winter Garden

                            5

                            Central Florida / Orlando

                            2 6 7 nights min

                            • 2 bedrooms
                            • sleeps 6
                            • 7 nights min
                            • Child friendly
                            • Air conditioning

                            from £230 / night

                            £1,608 / week

                            Book View

                            from £230 / night

                            Distance approx 29.95 km from Winter Garden

                              80

                              Florida / Old Town

                              3 8 2 nights min

                              • 3 bedrooms
                              • sleeps 8
                              • 2 nights min
                              • Nearest beach 25 km
                              • Child friendly

                              from £107 / night

                              £803 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 35 minutes

                              from £107 / night

                              Distance approx 30.41 km from Winter Garden

                                16

                                Central Florida / Kissimmee

                                8 16 7 nights min

                                • 8 bedrooms
                                • sleeps 16
                                • 7 nights min
                                • Swimming pool
                                • Air conditioning

                                from £406 / night

                                £2,839 / week

                                Book View

                                from £406 / night

                                Distance approx 27.11 km from Winter Garden

                                  12

                                  Central Florida / Kissimmee

                                  3 8 7 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Swimming pool
                                  • Child friendly
                                  • Car not necessary

                                  from £77 / night

                                  £535 - £857 / week

                                  Book View

                                  from £77 / night

                                  Distance approx 26.95 km from Winter Garden

                                    22

                                    Central Florida / Four Corners

                                    5 11 min stay varies

                                    • 5 bedrooms
                                    • sleeps 11
                                    • min stay varies
                                    • Swimming pool
                                    • Child friendly
                                    • Car not necessary

                                    from £185 / night

                                    £1,295 - £3,020 / week

                                    Book View

                                    from £185 / night

                                    Distance approx 26.06 km from Winter Garden Show on Map

                                      24

                                      Central Florida / Four Corners

                                      4 8 min stay varies

                                      • 4 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Swimming pool
                                      • Child friendly
                                      • Car not necessary

                                      from £133 / night

                                      £926 - £1,689 / week

                                      Book View

                                      from £133 / night

                                      Distance approx 30.99 km from Winter Garden

                                        16

                                        Central Florida / Four Corners

                                        4 8 7 nights min

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

                                        from £189 / night

                                        £1,320 / week

                                        Book View

                                        from £189 / night

                                        Distance approx 26.83 km from Winter Garden

                                          29

                                          Central Florida / Four Corners

                                          3 7 1 night min

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

                                          from £125 / night

                                          £870 / week

                                          Book View

                                          from £125 / night

                                          Distance approx 25.98 km from Winter Garden Show on Map

                                          (4) Excellent 

                                            46

                                            Central Florida / Kissimmee

                                            2 6 7 nights min

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

                                            from £143 / night

                                            £1,001 / week

                                            Book View

                                            from £143 / night

                                            Distance approx 20.18 km from Winter Garden

                                              30

                                              Central Florida / Orlando

                                              3 8 min stay varies

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

                                              from £143 / night

                                              £999 - £1,754 / week

                                              Book View

                                              from £143 / night

                                              Distance approx 26.85 km from Winter Garden

                                                37

                                                Central Florida / Four Corners

                                                7 19 min stay varies

                                                • 7 bedrooms
                                                • sleeps 19
                                                • min stay varies
                                                • Swimming pool
                                                • Child friendly
                                                • Air conditioning

                                                from £179 / night

                                                £1,251 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 9 minutes

                                                from £179 / night

                                                Distance approx 30.26 km from Winter Garden

                                                  16

                                                  Central Florida / Four Corners

                                                  6 12 7 nights min

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

                                                  from £216 / night

                                                  £1,508 / week

                                                  Book View

                                                  from £216 / night

                                                  Distance approx 26.75 km from Winter Garden

                                                  (22) Very Good 

                                                    37

                                                    Central Florida / Kissimmee

                                                    3 9 3 nights min

                                                    • 3 bedrooms
                                                    • sleeps 9
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £76 / night

                                                    £503 - £719 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 1 hour 33 minutes

                                                    from £76 / night

                                                    Distance approx 26.93 km from Winter Garden

                                                      11

                                                      Central Florida / Celebration

                                                      3 6 7 nights min

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

                                                      from £161 / night

                                                      £1,125 / week

                                                      Book View

                                                      from £161 / night

                                                      Distance approx 27.89 km from Winter Garden

                                                        33

                                                        Central Florida / Four Corners

                                                        2 4 min stay varies

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

                                                        from £108 / night

                                                        £754 / week

                                                        Book View

                                                        from £108 / night

                                                        Distance approx 19.04 km from Winter Garden

                                                          15

                                                          Central Florida / Orlando

                                                          2 8 7 nights min

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

                                                          from £179 / night

                                                          £1,251 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 3 hours 58 minutes

                                                          from £179 / night

                                                          Distance approx 30.66 km from Winter Garden

                                                          (2) Very Good 

                                                            22

                                                            Central Florida / Davenport

                                                            3 8 3 nights min

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

                                                            from £81 / night

                                                            £566 / week

                                                            Book View

                                                            from £81 / night

                                                            Distance approx 21.65 km from Winter Garden

                                                            (66) Excellent 

                                                              28

                                                              Lake County / Clermont

                                                              4 8 min stay varies

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

                                                              from £95 / night

                                                              £629 - £826 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 23 minutes

                                                              from £95 / night

                                                              Distance approx 25.75 km from Winter Garden Show on Map

                                                                43

                                                                Central Florida / Four Corners

                                                                5 10 min stay varies

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

                                                                from £196 / night

                                                                £1,368 / week

                                                                Book View

                                                                from £196 / night

                                                                Distance approx 26.33 km from Winter Garden

                                                                  27

                                                                  Central Florida / Kissimmee

                                                                  7 16 min stay varies

                                                                  • 7 bedrooms
                                                                  • sleeps 16
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Air conditioning

                                                                  from £270 / night

                                                                  £1,885 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 56 minutes

                                                                  from £270 / night

                                                                  Distance approx 31.77 km from Winter Garden

                                                                  (22) Very Good 

                                                                    18

                                                                    Central Florida / Kissimmee

                                                                    3 6 2 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • 2 nights min
                                                                    • Nearest beach 101 km
                                                                    • Swimming pool
                                                                    • Child friendly

                                                                    from £180 / night

                                                                    £1,261 / week

                                                                    Book View

                                                                    from £180 / night

                                                                    Distance approx 30.5 km from Winter Garden

                                                                      27

                                                                      Central Florida / Reunion

                                                                      5 12 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 12
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Ask owner if suitable for children
                                                                      • Ask about pets

                                                                      from £270 / night

                                                                      £1,702 - £2,509 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 3 hours 1 minutes

                                                                      from £270 / night

                                                                      Distance approx 21.29 km from Winter Garden

                                                                        23

                                                                        Central Florida / Orlando

                                                                        2 6 7 nights min

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

                                                                        from £152 / night

                                                                        £1,058 - £1,418 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 50 minutes

                                                                        from £152 / night

                                                                        Distance approx 28.46 km from Winter Garden

                                                                        (6) Excellent 

                                                                        Certificate of Excellence

                                                                          45

                                                                          Central Florida / Orlando

                                                                          4 8 min stay varies

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

                                                                          Certificate of Excellence

                                                                          from £103 / night

                                                                          £687 - £974 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 1 hour 48 minutes

                                                                          from £103 / night

                                                                          Distance approx 28.71 km from Winter Garden

                                                                          (74) Excellent 

                                                                            21

                                                                            Central Florida / Davenport

                                                                            4 8 4 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 4 nights min
                                                                            • Nearest beach 100 km
                                                                            • Swimming pool
                                                                            • Child friendly

                                                                            from £73 / night

                                                                            £504 - £626 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 3 hours 2 minutes

                                                                            from £73 / night

                                                                            Distance approx 19.94 km from Winter Garden

                                                                            (1) Excellent 

                                                                              13

                                                                              Lake County / Clermont

                                                                              1 4 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 1 night min
                                                                              • Child friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              from £63 / night

                                                                              £428 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 36 minutes

                                                                              from £63 / night

                                                                              Distance approx 31.77 km from Winter Garden

                                                                                24

                                                                                Central Florida / Reunion

                                                                                3 10 5 nights min

                                                                                • 3 bedrooms
                                                                                • sleeps 10
                                                                                • 5 nights min
                                                                                • Child friendly

                                                                                from £101 / night

                                                                                £676 / week

                                                                                Book View

                                                                                from £101 / night

                                                                                Distance approx 26.92 km from Winter Garden

                                                                                (1) Excellent 

                                                                                  17

                                                                                  Central Florida / Four Corners

                                                                                  6 12 7 nights min

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

                                                                                  from £126 / night

                                                                                  £883 / week

                                                                                  Book View

                                                                                  from £126 / night