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

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7,931 Holiday homes

    31

    Villa rental in Winter Haven

    Central Florida / Winter Haven

    2 7 min stay varies

    • 2 bedrooms
    • sleeps 7
    • min stay varies
    • Child friendly
    • Air conditioning

    from £104 / night

    £728 / week

    Book View

    from £104 / night

      24

      Villa rental in Winter Haven

      Central Florida / Winter Haven

      1 4 min stay varies

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

      from £91 / night

      £637 / week

      Book View

      from £91 / night

      (3) Very Good 

        22

        Holiday villa in Winter Haven

        Central Florida / Winter Haven

        3 6 4 nights min

        • 3 bedrooms
        • sleeps 6
        • 4 nights min
        • Nearest beach 126 km
        • Swimming pool
        • Child friendly

        from £108 / night

        £748 - £1,056 / week

        Book View

        Responds fast!
        avg. 3 hours 0 minutes

        from £108 / night

        (3) Excellent 

          20

          Holiday home in Winter Haven

          Central Florida / Winter Haven

          3 10 3 nights min

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

          from £195 / night

          £1,366 / week

          Book View

          from £195 / night

          (6) Excellent 

            28

            Holiday home in Winter Haven

            Central Florida / Winter Haven

            3 6 1 night min

            • 3 bedrooms
            • sleeps 6
            • 1 night min
            • Child friendly
            • Air conditioning
            • Private garden

            from £69 / night

            £432 / week

            Book View

            from £69 / night

              29

              Villa letting in Winter Haven

              Central Florida / Winter Haven

              1 4 min stay varies

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

              from £91 / night

              £637 / week

              Book View

              from £91 / night

              (2) Average 

                12

                Holiday home in Winter Haven

                Central Florida / Winter Haven

                1 3 1 night min

                • 1 bedroom
                • sleeps 3
                • 1 night min
                • Child friendly
                • Air conditioning
                • Ask about pets

                from £57 / night

                £349 / week

                Book View

                Responds fast!
                avg. 3 hours 33 minutes

                from £57 / night

                  28

                  Villa rental in Winter Haven

                  Central Florida / Winter Haven

                  1 4 min stay varies

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

                  from £91 / night

                  £637 / week

                  Book View

                  from £91 / night

                    34

                    Villa rental in Winter Haven

                    Central Florida / Winter Haven

                    2 6 min stay varies

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

                    from £104 / night

                    £728 / week

                    Book View

                    from £104 / night

                      33

                      Villa rental in Winter Haven

                      Central Florida / Winter Haven

                      2 7 min stay varies

                      • 2 bedrooms
                      • sleeps 7
                      • min stay varies
                      • Child friendly
                      • Air conditioning

                      from £104 / night

                      £728 / week

                      Book View

                      from £104 / night

                        10

                        Holiday home in Winter Haven

                        Central Florida / Winter Haven

                        2 5 120 nights min

                        • 2 bedrooms
                        • sleeps 5
                        • 120 nights min
                        • Air conditioning
                        • Pet friendly
                        • Private garden

                        from £54 / night

                        £375 / week

                        Book View

                        from £54 / night

                        Great rentals within 20 miles that match your search

                        Distance approx 18.8 miles from Winter Haven

                        (17) Excellent 

                          25

                          Holiday villa in Davenport

                          Davenport / Lake Wilson Preserve

                          4 8 min stay varies

                          • 4 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Nearest beach 90 km
                          • Swimming pool
                          • Child friendly

                          from £103 / night

                          £722 - £962 / week

                          Book View

                          Responds fast!
                          avg. 53 minutes

                          from £103 / night

                          Distance approx 19.11 miles from Winter Haven

                          (10) Very Good 

                            28

                            Holiday villa in Davenport

                            Davenport / Sandy Ridge

                            4 10 5 nights min

                            • 4 bedrooms
                            • sleeps 10
                            • 5 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 127 km
                            • Swimming pool

                            from £115 / night

                            £613 / week

                            Book View

                            Responds fast!
                            avg. 1 hour 5 minutes

                            from £115 / night

                            Distance approx 18.32 miles from Winter Haven

                              10

                              Holiday villa in ChampionsGate

                              Central Florida / ChampionsGate

                              3 6 min stay varies

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

                              from £97 / night

                              £679 - £823 / week

                              Book View

                              from £97 / night

                              Distance approx 12.28 miles from Winter Haven

                              (5) Excellent 

                                46

                                Davenport holiday home rental

                                Central Florida / Davenport

                                5 10 7 nights min

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

                                from £124 / night

                                £864 / week

                                Book View

                                Responds fast!
                                avg. 51 minutes

                                from £124 / night

                                Distance approx 18.97 miles from Winter Haven

                                (3) Excellent 

                                  15

                                  Villa rental in Davenport with swimming pool, golf nearby

                                  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 42 minutes

                                  from £103 / night

                                  Distance approx 18.06 miles from Winter Haven

                                  (3) Excellent 

                                    28

                                    Davenport holiday home let

                                    Davenport / Calabay Parc

                                    5 8 7 nights min

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

                                    from £123 / night

                                    £859 / week

                                    Book View

                                    Responds fast!
                                    avg. 3 hours 54 minutes

                                    from £123 / night

                                    Distance approx 10.17 miles from Winter Haven Show on Map

                                    (43) Excellent 

                                      51

                                      Holiday villa rental

                                      Haines City / Calabay Parc at Tower Lake

                                      4 10 min stay varies

                                      • 4 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 50 km
                                      • Swimming pool

                                      from £149 / night

                                      £1,042 / week

                                      Book View

                                      from £149 / night

                                      Distance approx 16.79 miles from Winter Haven

                                        54

                                        Holiday home in Davenport

                                        Central Florida / Davenport

                                        5 11 min stay varies

                                        • 5 bedrooms
                                        • sleeps 11
                                        • min stay varies
                                        • Child friendly

                                        from £144 / night

                                        £865 - £1,123 / week

                                        Book View

                                        from £144 / night

                                        Distance approx 11.93 miles from Winter Haven

                                          28

                                          Holiday villa in Davenport

                                          Central Florida / Davenport

                                          5 11 4 nights min

                                          • 5 bedrooms
                                          • sleeps 11
                                          • 4 nights min
                                          • Swimming pool
                                          • Child friendly
                                          • Air conditioning

                                          from £235 / night

                                          £951 / week

                                          Book View

                                          from £235 / night

                                          Distance approx 16.69 miles from Winter Haven

                                            25

                                            Holiday villa in Sand Lake

                                            Florida / Sand Lake

                                            4 8 min stay varies

                                            • 4 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Nearest beach 103 km
                                            • Swimming pool
                                            • Child friendly

                                            from £103 / night

                                            £710 - £962 / week

                                            Book View

                                            from £103 / night

                                            Distance approx 18.01 miles from Winter Haven

                                              24

                                              Holiday apartment in ChampionsGate

                                              Central Florida / ChampionsGate

                                              2 6 6 nights min

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

                                              from £70 / night

                                              £485 / week

                                              Book View

                                              Responds fast!
                                              avg. 9 minutes

                                              from £70 / night

                                              Distance approx 18.8 miles from Winter Haven

                                              (4) Excellent 

                                                29

                                                Holiday home with swimming pool in Reunion

                                                Central Florida / Reunion

                                                4 8 min stay varies

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

                                                from £131 / night

                                                £958 - £1,960 / week

                                                Book View

                                                from £131 / night

                                                Distance approx 16.71 miles from Winter Haven

                                                (10) Excellent 

                                                Certificate of Excellence

                                                  28

                                                  Home rental in Davenport with swimming pool

                                                  Central Florida / Davenport

                                                  6 14 7 nights min

                                                  • 6 bedrooms
                                                  • sleeps 14
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Air conditioning

                                                  Certificate of Excellence

                                                  from £114 / night

                                                  £854 - £2,043 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 44 minutes

                                                  from £114 / night

                                                  Distance approx 18.54 miles from Winter Haven

                                                    12

                                                    Villa rental in Davenport with shared pool

                                                    Central Florida / Davenport

                                                    4 6 7 nights min

                                                    • 4 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Nearest beach 97 km
                                                    • Swimming pool
                                                    • Child friendly

                                                    from £126 / night

                                                    £876 / week

                                                    Book View

                                                    from £126 / night

                                                    Distance approx 17.09 miles from Winter Haven

                                                    (1) Excellent 

                                                      33

                                                      ChampionsGate holiday home rental

                                                      Central Florida / ChampionsGate

                                                      7 16 4 nights min

                                                      • 7 bedrooms
                                                      • sleeps 16
                                                      • 4 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £260 / night

                                                      £1,819 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 48 minutes

                                                      from £260 / night

                                                      Distance approx 17.27 miles from Winter Haven

                                                      (4) Excellent 

                                                        76

                                                        Holiday villa with swimming pool, golf nearby in Davenport

                                                        Central Florida / Davenport

                                                        8 20 min stay varies

                                                        • 8 bedrooms
                                                        • sleeps 20
                                                        • min stay varies
                                                        • Nearest beach 90 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £202 / night

                                                        £1,656 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 51 minutes

                                                        from £202 / night

                                                        Distance approx 19.32 miles from Winter Haven

                                                        (7) Excellent 

                                                          23

                                                          Davenport holiday home rental

                                                          Central Florida / Davenport

                                                          4 8 4 nights min

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

                                                          from £118 / night

                                                          £823 / week

                                                          Book View

                                                          from £118 / night

                                                          Distance approx 17.48 miles from Winter Haven

                                                            21

                                                            Holiday home with shared pool, golf nearby in ChampionsGate

                                                            Central Florida / ChampionsGate

                                                            4 10 5 nights min

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

                                                            from £105 / night

                                                            £732 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 7 minutes

                                                            from £105 / night

                                                            Distance approx 17.69 miles from Winter Haven

                                                            (4) Excellent 

                                                              14

                                                              Holiday home in Davenport

                                                              Central Florida / Davenport

                                                              4 10 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 10
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Air conditioning

                                                              from £84 / night

                                                              £586 / week

                                                              Book View

                                                              from £84 / night

                                                              Distance approx 10.13 miles from Winter Haven Show on Map

                                                              (1) Excellent 

                                                                24

                                                                Holiday villa in Haines City

                                                                Central Florida / Haines City

                                                                5 12 5 nights min

                                                                • 5 bedrooms
                                                                • sleeps 12
                                                                • 5 nights min
                                                                • Nearest beach 72 km
                                                                • Swimming pool
                                                                • Child friendly

                                                                from £105 / night

                                                                £732 / week

                                                                Book View

                                                                from £105 / night

                                                                Distance approx 17.58 miles from Winter Haven

                                                                (15) Excellent 

                                                                Certificate of Excellence

                                                                  27

                                                                  Villa rental in Davenport

                                                                  Central Florida / Davenport

                                                                  4 8 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Nearest beach 126 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  Certificate of Excellence

                                                                  from £70 / night

                                                                  £732 - £976 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 22 minutes

                                                                  from £70 / night

                                                                  Distance approx 12.26 miles from Winter Haven

                                                                    33

                                                                    Holiday home rental

                                                                    Central Florida / Davenport

                                                                    5 10 min stay varies

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

                                                                    from £146 / night

                                                                    £1,021 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 12 minutes

                                                                    from £146 / night

                                                                    Distance approx 16.68 miles from Winter Haven

                                                                      52

                                                                      Home rental in Loughman with swimming pool

                                                                      Central Florida / Loughman

                                                                      4 10 min stay varies

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

                                                                      from £124 / night

                                                                      £866 / week

                                                                      Book View

                                                                      from £124 / night

                                                                      Distance approx 18.5 miles from Winter Haven

                                                                        20

                                                                        Home letting in Loughman with swimming pool

                                                                        Central Florida / Loughman

                                                                        4 9 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 9
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Car not necessary
                                                                        • Air conditioning

                                                                        from £138 / night

                                                                        £967 - £1,534 / week

                                                                        Book View

                                                                        from £138 / night

                                                                        Distance approx 19.8 miles from Winter Haven

                                                                          5

                                                                          Holiday caravan/mobile home in Lake Wales

                                                                          Central Florida / Lake Wales

                                                                          1 4 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Suitable for children age 5+

                                                                          from £86 / night

                                                                          £389 - £449 / week

                                                                          Book View

                                                                          from £86 / night

                                                                          Distance approx 19.86 miles from Winter Haven

                                                                            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 £183 / night

                                                                            £1,279 / week

                                                                            Book View

                                                                            from £183 / night

                                                                            Distance approx 19.63 miles from Winter Haven

                                                                              16

                                                                              Holiday villa with swimming pool in Four Corners

                                                                              Central Florida / Four Corners

                                                                              5 10 7 nights min

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

                                                                              from £183 / night

                                                                              £1,279 / week

                                                                              Book View

                                                                              from £183 / night

                                                                              Distance approx 19.27 miles from Winter Haven

                                                                              (1)  

                                                                                27

                                                                                Home rental in Davenport with swimming pool

                                                                                Central Florida / Davenport

                                                                                5 10 5 nights min

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

                                                                                from £95 / night

                                                                                £665 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 9 minutes

                                                                                from £95 / night

                                                                                Distance approx 17.27 miles from Winter Haven

                                                                                  53

                                                                                  Holiday home with golf nearby in ChampionsGate

                                                                                  Central Florida / ChampionsGate

                                                                                  9 20 min stay varies

                                                                                  • 9 bedrooms
                                                                                  • sleeps 20
                                                                                  • min stay varies
                                                                                  • Swimming pool
                                                                                  • Child friendly
                                                                                  • Air conditioning

                                                                                  from £243 / night

                                                                                  £1,695 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 3 hours 6 minutes

                                                                                  from £243 / night

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