Apartments in Winter Garden and Houses - Holiday Lettings - Holiday Rentals Winter Garden

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13,604 Holiday homes

(3) Excellent 

    25

    Winter Garden holiday home rental

    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 31 minutes

    from £63 / night

    (2) Excellent 

      16

      Home rental in Winter Garden

      Central Florida / Winter Garden

      3 7 1 night min

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

      from £70 / night

      £505 / week

      Book View

      Responds fast!
      avg. 3 hours 17 minutes

      from £70 / night

        6

        Home rental in Winter Garden

        Central Florida / Winter Garden

        4 8 3 nights min

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

        from £111 / night

        £665 / week

        Book View

        from £111 / night

        (19) Excellent 

        Certificate of Excellence

          31

          Holiday villa in Winter Garden

          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

            Camper van accommodation in Winter Garden

            Central Florida / Winter Garden

            3 8 3 nights min

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

            from £111 / night

            £705 / week

            Book View

            Responds fast!
            avg. 2 hours 14 minutes

            from £111 / night

            (2) Very Good 

              8

              Holiday home in Winter Garden

              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. 2 hours 33 minutes

              from £75 / night

                10

                Holiday condo in Winter Garden

                Central Florida / Winter Garden

                2 6 3 nights min

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

                from £173 / night

                £1,210 / week

                Book View

                Responds fast!
                avg. 3 hours 42 minutes

                from £173 / night

                  9

                  Winter Garden holiday hotel apartment rental

                  Central Florida / Winter Garden

                  2 6 7 nights min

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

                  from £62 / night

                  £435 / week

                  Book View

                  from £62 / night

                  Great rentals within 20 miles that match your search

                  Distance approx 13.6 miles from Winter Garden

                  (24) Excellent 

                  Certificate of Excellence

                    24

                    Holiday villa rental with swimming pool

                    Lake County / Clermont

                    4 8 7 nights min

                    • 4 bedrooms
                    • sleeps 8
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 130 km
                    • Swimming pool

                    Certificate of Excellence

                    from £116 / night

                    £621 - £962 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 7 minutes

                    from £116 / night

                    Distance approx 19.55 miles from Winter Garden

                    (2) Average 

                      17

                      Holiday home in Orlando

                      Central Florida / Orlando

                      5 10 4 nights min

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

                      from £126 / night

                      £796 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 0 minutes

                      from £126 / night

                      Distance approx 19.57 miles from Winter Garden

                      (41) Very Good 

                      Certificate of Excellence

                        18

                        Kissimmee holiday townhouse rental

                        Kissimmee / Venetian Bay Villages

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Nearest beach 55 km
                        • Swimming pool

                        Certificate of Excellence

                        from £63 / night

                        £441 - £465 / week

                        Book View

                        Responds fast!
                        avg. 1 hour 52 minutes

                        from £63 / night

                        Distance approx 17.39 miles from Winter Garden

                          14

                          Holiday villa in Davenport

                          Central Florida / Davenport

                          6 12 7 nights min

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

                          from £151 / night

                          £1,055 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 13 minutes

                          from £151 / night

                          Distance approx 18.66 miles from Winter Garden

                          (2) Excellent 

                            19

                            Holiday villa with golf nearby in Davenport

                            Davenport / Highlands Reserve Golf Course

                            5 10 min stay varies

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

                            from £155 / night

                            £1,082 / week

                            Book View

                            Responds fast!
                            avg. 41 minutes

                            from £155 / night

                            Distance approx 16.67 miles from Winter Garden

                              11

                              Four Corners holiday home rental

                              Central Florida / Four Corners

                              4 10 min stay varies

                              • 4 bedrooms
                              • sleeps 10
                              • min stay varies
                              • Child friendly
                              • Air conditioning

                              from £111 / night

                              £776 / week

                              Book View

                              from £111 / night

                              Distance approx 16.55 miles from Winter Garden

                              (5) Excellent 

                                29

                                Holiday villa in Kissimmee

                                Kissimmee / Emerald Isle Kissimmee

                                4 8 5 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 5 nights min
                                • Nearest beach 90 km
                                • Swimming pool
                                • Child friendly

                                from £125 / night

                                £869 - £1,261 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 59 minutes

                                from £125 / night

                                Distance approx 15.01 miles from Winter Garden Show on Map

                                (1) Excellent 

                                  5

                                  Holiday villa with shared pool, golf nearby in Kissimmee

                                  Kissimmee / Orange Lake Resort

                                  2 8 7 nights min

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

                                  from £133 / night

                                  £931 / week

                                  Book View

                                  from £133 / night

                                  Distance approx 17.22 miles from Winter Garden

                                  (21) Excellent 

                                    28

                                    Holiday villa in Kissimmee

                                    Kissimmee / Windsor Palms

                                    6 13 5 nights min

                                    • 6 bedrooms
                                    • sleeps 13
                                    • 5 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child friendly

                                    from £218 / night

                                    £1,523 / week

                                    Book View

                                    Responds fast!
                                    avg. 3 hours 20 minutes

                                    from £218 / night

                                    Distance approx 16.38 miles from Winter Garden

                                      19

                                      Kissimmee holiday home accommodation

                                      Kissimmee / Emerald Isle Kissimmee

                                      3 8 min stay varies

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

                                      from £58 / night

                                      £458 / week

                                      Book View

                                      from £58 / night

                                      Distance approx 16.72 miles from Winter Garden

                                        46

                                        Holiday condo rental

                                        Central Florida / Four Corners

                                        3 9 min stay varies

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

                                        from £132 / night

                                        £925 / week

                                        Book View

                                        Responds fast!
                                        avg. 34 minutes

                                        from £132 / night

                                        Distance approx 18.11 miles from Winter Garden

                                        (7) Excellent 

                                          24

                                          Holiday villa with golf nearby in Kissimmee

                                          Kissimmee / Indian Ridge Oaks

                                          5 10 5 nights min

                                          • 5 bedrooms
                                          • sleeps 10
                                          • 5 nights min
                                          • Nearest beach 60 km
                                          • Swimming pool
                                          • Child friendly

                                          from £161 / night

                                          £1,145 - £1,260 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 57 minutes

                                          from £161 / night

                                          Distance approx 17.15 miles from Winter Garden

                                          (31) Excellent 

                                            42

                                            Holiday villa in Kissimmee

                                            Central Florida / Kissimmee

                                            3 8 5 nights min

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

                                            from £99 / night

                                            £689 / week

                                            Book View

                                            Responds fast!
                                            avg. 2 hours 33 minutes

                                            from £99 / night

                                            Distance approx 17.77 miles from Winter Garden

                                              22

                                              Holiday villa in Davenport

                                              Central Florida / Davenport

                                              5 10 min stay varies

                                              • 5 bedrooms
                                              • sleeps 10
                                              • min stay varies
                                              • Nearest beach 135 km
                                              • Swimming pool
                                              • Child friendly

                                              from £131 / night

                                              £913 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 21 minutes

                                              from £131 / night

                                              Distance approx 17.05 miles from Winter Garden

                                              (3) Excellent 

                                                21

                                                Kissimmee holiday home rental

                                                Central Florida / Kissimmee

                                                5 10 3 nights min

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

                                                from £200 / night

                                                £1,397 / week

                                                Book View

                                                from £200 / night

                                                Distance approx 16.36 miles from Winter Garden

                                                  24

                                                  Holiday townhouse with golf nearby in Kissimmee

                                                  Kissimmee / Kissimmee City

                                                  3 6 5 nights min

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

                                                  from £88 / night

                                                  £559 / week

                                                  Book View

                                                  from £88 / night

                                                  Distance approx 17.01 miles from Winter Garden

                                                    19

                                                    Holiday home rental

                                                    Central Florida / Kissimmee

                                                    6 12 min stay varies

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

                                                    from £177 / night

                                                    £1,506 - £2,216 / week

                                                    Book View

                                                    from £177 / night

                                                    Distance approx 16.68 miles from Winter Garden

                                                    (9) Excellent 

                                                      28

                                                      Holiday condo with shared pool in Kissimmee

                                                      Kissimmee / Windsor Hills Resort

                                                      3 8 2 nights min

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

                                                      from £88 / night

                                                      £647 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 1 hour 45 minutes

                                                      from £88 / night

                                                      Distance approx 13.97 miles from Winter Garden

                                                      (8) Very Good 

                                                        14

                                                        Holiday condo with shared pool in Orlando

                                                        Central Florida / Orlando

                                                        2 8 2 nights min

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

                                                        from £169 / night

                                                        £1,241 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 42 minutes

                                                        from £169 / night

                                                        Distance approx 16.7 miles from Winter Garden

                                                          19

                                                          Holiday villa in Kissimmee

                                                          Kissimmee / Emerald Isle Kissimmee

                                                          5 12 min stay varies

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

                                                          from £142 / night

                                                          £838 - £1,299 / week

                                                          Book View

                                                          from £142 / night

                                                          Distance approx 18.95 miles from Winter Garden

                                                            27

                                                            Holiday condo rental

                                                            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 £266 / night

                                                            £1,676 - £2,793 / week

                                                            Book View

                                                            from £266 / night

                                                            Distance approx 16.15 miles from Winter Garden Show on Map

                                                              12

                                                              Apartment rental in Four Corners with swimming pool

                                                              Central Florida / Four Corners

                                                              4 10 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 10
                                                              • 2 nights min
                                                              • Swimming pool
                                                              • Child friendly
                                                              • Car not necessary

                                                              from £195 / night

                                                              £1,359 - £1,545 / week

                                                              Book View

                                                              from £195 / night

                                                              Distance approx 16.11 miles from Winter Garden

                                                              (20) Excellent 

                                                              Certificate of Excellence

                                                                35

                                                                Holiday home with golf nearby in Kissimmee

                                                                Kissimmee / Encantada Resort

                                                                3 8 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 80 km
                                                                • Swimming pool

                                                                Certificate of Excellence

                                                                from £79 / night

                                                                £532 - £732 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 1 hour 48 minutes

                                                                from £79 / night

                                                                Distance approx 17.15 miles from Winter Garden

                                                                  47

                                                                  Four Corners holiday condo rental

                                                                  Central Florida / Four Corners

                                                                  3 8 3 nights min

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

                                                                  from £133 / night

                                                                  £931 / week

                                                                  Book View

                                                                  from £133 / night

                                                                  Distance approx 16.47 miles from Winter Garden

                                                                    11

                                                                    Hotel apartment rental in Four Corners

                                                                    Central Florida / Four Corners

                                                                    2 8 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 8
                                                                    • 7 nights min
                                                                    • Child friendly

                                                                    from £65 / night

                                                                    £453 / week

                                                                    Book View

                                                                    from £65 / night

                                                                    Distance approx 16.84 miles from Winter Garden

                                                                      77

                                                                      Kissimmee holiday villa rental

                                                                      Central Florida / Kissimmee

                                                                      5 10 5 nights min

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

                                                                      from £172 / night

                                                                      £1,145 / week

                                                                      Book View

                                                                      from £172 / night

                                                                      Distance approx 17.53 miles from Winter Garden

                                                                        12

                                                                        Hotel apartment rental in Kissimmee

                                                                        Central Florida / Kissimmee

                                                                        2 6 7 nights min

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

                                                                        from £70 / night

                                                                        £491 / week

                                                                        Book View

                                                                        from £70 / night

                                                                        Distance approx 15.11 miles from Winter Garden Show on Map

                                                                          20

                                                                          Holiday villa with shared pool in Orlando

                                                                          Central Florida / Orlando

                                                                          2 8 4 nights min

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

                                                                          from £133 / night

                                                                          £931 / week

                                                                          Book View

                                                                          from £133 / night

                                                                          Distance approx 13.27 miles from Winter Garden

                                                                            18

                                                                            Holiday villa in Orlando

                                                                            Central Florida / Orlando

                                                                            4 12 2 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 12
                                                                            • 2 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £778 / night

                                                                            £5,442 / week

                                                                            Book View

                                                                            from £778 / night

                                                                            Distance approx 17.48 miles from Winter Garden

                                                                              22

                                                                              Holiday villa in Kissimmee

                                                                              Central Florida / Kissimmee

                                                                              6 12 min stay varies

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

                                                                              from £265 / night

                                                                              £1,152 - £2,845 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 43 minutes

                                                                              from £265 / night

                                                                              Distance approx 16.82 miles from Winter Garden

                                                                                23

                                                                                Holiday home with swimming pool in Four Corners

                                                                                Central Florida / Four Corners

                                                                                7 16 3 nights min

                                                                                • 7 bedrooms
                                                                                • sleeps 16
                                                                                • 3 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £285 / night

                                                                                £1,918 - £3,494 / week

                                                                                Book View

                                                                                from £285 / night

                                                                                Distance approx 16.23 miles from Winter Garden

                                                                                  24

                                                                                  Holiday home with swimming pool in Kissimmee

                                                                                  Central Florida / Kissimmee

                                                                                  7 16 min stay varies

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

                                                                                  from £479 / night

                                                                                  £3,351 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 56 minutes

                                                                                  from £479 / night

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