Houses in Oldsmar and Villas – Holiday Lettings - Holiday Rentals Oldsmar

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

2,262 Holiday homes

(2) Very Good 

    11

    Oldsmar holiday condo rental

    Florida / Oldsmar

    2 4 5 nights min

    • 2 bedrooms
    • sleeps 4
    • 5 nights min
    • Swimming pool
    • Air conditioning

    from £60 / night

    £416 / week

    Book View

    Responds fast!
    avg. 2 hours 54 minutes

    from £60 / night

      29

      Oldsmar holiday home rental

      Florida / Oldsmar

      3 5 min stay varies

      • 3 bedrooms
      • sleeps 5
      • min stay varies
      • Air conditioning
      • Pet friendly
      • Private garden

      from £89 / night

      £621 - £896 / week

      Book View

      from £89 / night

        19

        Holiday home in Oldsmar

        Florida / Oldsmar

        3 6 4 nights min

        • 3 bedrooms
        • sleeps 6
        • 4 nights min
        • Beach / lakeside relaxation
        • Child friendly
        • Air conditioning

        from £132 / night

        £919 / week

        Book View

        from £132 / night

          16

          Holiday villa with shared pool in Oldsmar

          Florida / Oldsmar

          2 4 90 nights min

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

          from £178 / night

          £1,108 / week

          Book View

          from £178 / night

          Great rentals within 20 miles that match your search

          Distance approx 9.74 miles from Oldsmar

            4

            Home rental in Clearwater with shared pool

            Florida / Clearwater

            1 3 1 night min

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

            from £177 / night

            £1,235 / week

            Book View

            from £177 / night

            Distance approx 19.22 miles from Oldsmar

              28

              Home letting in Tampa

              Florida / Tampa

              4 10 7 nights min

              • 4 bedrooms
              • sleeps 10
              • 7 nights min
              • Child friendly
              • Air conditioning

              from £132 / night

              £925 / week

              Book View

              Responds fast!
              avg. 59 minutes

              from £132 / night

              Distance approx 15 miles from Oldsmar

              (4) Excellent 

                24

                Holiday home in Indian Rocks Beach

                Florida / Indian Rocks Beach

                2 6 7 nights min

                • 2 bedrooms
                • sleeps 6
                • 7 nights min
                • Beach / lakeside relaxation
                • Nearest beach 0 km
                • Child friendly

                from £133 / night

                £705 / week

                Book View

                from £133 / night

                Distance approx 15.81 miles from Oldsmar

                (1) Excellent 

                  19

                  Holiday condo in Indian Rocks Beach

                  Florida / Indian Rocks Beach

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child friendly

                  from £129 / night

                  £820 - £1,654 / week

                  Book View

                  from £129 / night

                  Distance approx 8.03 miles from Oldsmar

                  (2) Very Good 

                    16

                    Crystal Beach holiday studio rental

                    Florida / Crystal Beach

                    Studio 1 3 nights min

                    • Studio
                    • sleeps 1
                    • 3 nights min
                    • Nearest beach 0.15 km
                    • Child friendly
                    • Air conditioning

                    from £89 / night

                    £532 / week

                    Book View

                    Responds fast!
                    avg. 27 minutes

                    from £89 / night

                    Distance approx 15.6 miles from Oldsmar

                    (3) Excellent 

                      28

                      Indian Rocks Beach holiday condo accommodation

                      Florida / Indian Rocks Beach

                      2 10 3 nights min

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

                      from £265 / night

                      £1,856 / week

                      Book View

                      from £265 / night

                      Distance approx 14.83 miles from Oldsmar

                        23

                        Holiday home with golf nearby in New Port Richey

                        Florida / New Port Richey

                        2 4 60 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 60 nights min
                        • Swimming pool
                        • Air conditioning

                        from £62 / night

                        £435 / week

                        Book View

                        Responds fast!
                        avg. 1 hour 32 minutes

                        from £62 / night

                        Distance approx 8.15 miles from Oldsmar

                        (9) Excellent 

                          46

                          Holiday apartment rental

                          Florida / Clearwater

                          1 3 2 nights min

                          • 1 bedroom
                          • sleeps 3
                          • 2 nights min
                          • Child friendly
                          • Air conditioning
                          • Pet friendly

                          from £62 / night

                          £373 - £532 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 23 minutes

                          from £62 / night

                          Distance approx 11.79 miles from Oldsmar

                            35

                            Holiday home in Largo

                            Florida / Largo

                            1 6 3 nights min

                            • 1 bedroom
                            • sleeps 6
                            • 3 nights min
                            • Nearest beach 8 km
                            • Child friendly
                            • Air conditioning

                            from £70 / night

                            £491 / week

                            Book View

                            from £70 / night

                            Distance approx 10.58 miles from Oldsmar

                              24

                              Holiday studio letting

                              Florida / Clearwater

                              Studio 2 min stay varies

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

                              from £106 / night

                              £739 / week

                              Book View

                              Responds fast!
                              avg. 19 minutes

                              from £106 / night

                              Distance approx 10.84 miles from Oldsmar

                              (14) Excellent 

                              Certificate of Excellence

                                47

                                Holiday apartment in Clearwater

                                Clearwater / Clearwater Beach

                                4 3 nights min

                                • sleeps 4
                                • 3 nights min
                                • Beach / lakeside relaxation
                                • Nearest beach 0.4 km
                                • Swimming pool

                                Certificate of Excellence

                                from £89 / night

                                £532 - £1,064 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 7 minutes

                                from £89 / night

                                Distance approx 16.67 miles from Oldsmar

                                (2) Very Good 

                                  39

                                  Holiday condo rental

                                  Florida / Bay Pines

                                  1 5 min stay varies

                                  • 1 bedroom
                                  • sleeps 5
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Child friendly

                                  from £86 / night

                                  £554 - £829 / week

                                  Book View

                                  Responds fast!
                                  avg. 1 hour 0 minutes

                                  from £86 / night

                                  Distance approx 17.03 miles from Oldsmar

                                    12

                                    Holiday condo rental

                                    Florida / Indian Shores

                                    2 6 7 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 7 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.2 km
                                    • Child friendly

                                    from £241 / night

                                    £1,685 / week

                                    Book View

                                    from £241 / night

                                    Distance approx 17.36 miles from Oldsmar

                                      20

                                      Home accommodation in Tampa

                                      Florida / Tampa

                                      3 6 3 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Beach / lakeside relaxation
                                      • Suitable for children age 5+

                                      from £156 / night

                                      £1,086 / week

                                      Book View

                                      from £156 / night

                                      Distance approx 9.65 miles from Oldsmar

                                      (5) Excellent 

                                        38

                                        Condo rental in Clearwater

                                        Florida / Clearwater

                                        1 3 min stay varies

                                        • 1 bedroom
                                        • sleeps 3
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Nearest beach 7 km
                                        • Swimming pool

                                        from £58 / night

                                        £404 / week

                                        Book View

                                        from £58 / night

                                        Distance approx 19.46 miles from Oldsmar

                                          30

                                          Holiday condo with shared pool in Tampa

                                          Florida / Tampa

                                          2 4 4 nights min

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

                                          from £79 / night

                                          £553 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 42 minutes

                                          from £79 / night

                                          Distance approx 14.08 miles from Oldsmar

                                          (2) Average 

                                            24

                                            Holiday home in Largo

                                            Florida / Largo

                                            4 10 min stay varies

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

                                            from £222 / night

                                            £1,552 / week

                                            Book View

                                            Responds fast!
                                            avg. 19 minutes

                                            from £222 / night

                                            Distance approx 12.03 miles from Oldsmar

                                              17

                                              Holiday home in Trinity

                                              Florida / Trinity

                                              3 6 3 nights min

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

                                              from £107 / night

                                              £745 / week

                                              Book View

                                              from £107 / night

                                              Distance approx 9.68 miles from Oldsmar

                                              (7) Excellent 

                                                16

                                                Clearwater holiday condo rental

                                                Florida / Clearwater

                                                1 2 min stay varies

                                                • 1 bedroom
                                                • sleeps 2
                                                • min stay varies
                                                • Swimming pool
                                                • Ask owner if suitable for children
                                                • Air conditioning

                                                from £65 / night

                                                £488 - £710 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 40 minutes

                                                from £65 / night

                                                Distance approx 15.24 miles from Oldsmar

                                                (4) Excellent 

                                                Certificate of Excellence

                                                  16

                                                  Indian Rocks Beach holiday condo rental

                                                  Florida / Indian Rocks Beach

                                                  2 6 7 nights min

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

                                                  Certificate of Excellence

                                                  from £173 / night

                                                  £927 - £1,414 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 5 minutes

                                                  from £173 / night

                                                  Distance approx 10.19 miles from Oldsmar

                                                  (1) Excellent 

                                                    15

                                                    Clearwater holiday condo rental

                                                    Florida / Clearwater

                                                    2 4 90 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 90 nights min
                                                    • Nearest beach 2 km
                                                    • Child friendly
                                                    • Car not necessary

                                                    from £70 / night

                                                    £488 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 hours 55 minutes

                                                    from £70 / night

                                                    Distance approx 17.43 miles from Oldsmar

                                                      56

                                                      Holiday apartment in Indian Shores

                                                      Florida / Indian Shores

                                                      2 4 7 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 0 km
                                                      • Swimming pool

                                                      from £140 / night

                                                      £975 - £2,217 / week

                                                      Book View

                                                      from £140 / night

                                                      Distance approx 18.4 miles from Oldsmar

                                                        24

                                                        Holiday condo rental

                                                        Florida / Madeira Beach

                                                        2 6 14 nights min

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

                                                        from £133 / night

                                                        £1,241 / week

                                                        Book View

                                                        from £133 / night

                                                        Distance approx 18.4 miles from Oldsmar

                                                          10

                                                          Holiday apartment in Madeira Beach

                                                          Florida / Madeira Beach

                                                          2 6 14 nights min

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

                                                          from £284 / night

                                                          £1,986 / week

                                                          Book View

                                                          from £284 / night

                                                          Distance approx 9.68 miles from Oldsmar

                                                          (36) Excellent 

                                                          Certificate of Excellence

                                                            50

                                                            Holiday condo in Clearwater

                                                            Florida / Clearwater

                                                            2 6 7 nights min

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

                                                            Certificate of Excellence

                                                            from £89 / night

                                                            £621 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 22 minutes

                                                            from £89 / night

                                                            Distance approx 10.97 miles from Oldsmar

                                                              15

                                                              Holiday condo in Clearwater

                                                              Florida / Clearwater

                                                              2 6 7 nights min

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

                                                              from £266 / night

                                                              £1,862 / week

                                                              Book View

                                                              from £266 / night

                                                              Distance approx 14.27 miles from Oldsmar

                                                              (1) Excellent 

                                                                62

                                                                Holiday home with swimming pool in Indian Rocks Beach

                                                                Florida / Indian Rocks Beach

                                                                4 12 min stay varies

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

                                                                from £271 / night

                                                                £1,893 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 55 minutes

                                                                from £271 / night

                                                                Distance approx 10.97 miles from Oldsmar

                                                                  6

                                                                  Clearwater holiday condo rental

                                                                  Florida / Clearwater

                                                                  1 4 7 nights min

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

                                                                  from £200 / night

                                                                  £1,241 / week

                                                                  Book View

                                                                  from £200 / night

                                                                  Distance approx 18.42 miles from Oldsmar

                                                                    42

                                                                    Holiday condo with shared pool in Madeira Beach

                                                                    Florida / Madeira Beach

                                                                    2 6 4 nights min

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

                                                                    from £297 / night

                                                                    £2,079 - £7,608 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 3 hours 39 minutes

                                                                    from £297 / night

                                                                    Distance approx 8.31 miles from Oldsmar

                                                                      40

                                                                      Odessa holiday home rental

                                                                      Florida / Odessa

                                                                      5 10 7 nights min

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

                                                                      from £528 / night

                                                                      £3,692 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 55 minutes

                                                                      from £528 / night

                                                                      Distance approx 18.4 miles from Oldsmar

                                                                      (1) Excellent 

                                                                        27

                                                                        Holiday apartment with shared pool in Madeira Beach

                                                                        Florida / Madeira Beach

                                                                        2 6 8 nights min

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

                                                                        from £334 / night

                                                                        £2,334 - £7,608 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 3 hours 35 minutes

                                                                        from £334 / night

                                                                        Distance approx 13.31 miles from Oldsmar

                                                                        (1)  

                                                                          36

                                                                          Tampa holiday home rental

                                                                          Florida / Tampa

                                                                          4 6 2 nights min

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

                                                                          from £173 / night

                                                                          £1,197 / week

                                                                          Book View

                                                                          from £173 / night

                                                                          Distance approx 16.54 miles from Oldsmar

                                                                          (1) Excellent 

                                                                            25

                                                                            Indian Shores holiday bungalow rental

                                                                            Florida / Indian Shores

                                                                            4 5 7 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 5
                                                                            • 7 nights min
                                                                            • Child friendly
                                                                            • Air conditioning
                                                                            • Private garden

                                                                            from £239 / night

                                                                            £1,670 / week

                                                                            Book View

                                                                            from £239 / night

                                                                            Distance approx 16.39 miles from Oldsmar

                                                                              27

                                                                              Indian Shores holiday apartment rental

                                                                              Florida / Indian Shores

                                                                              3 7 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 7
                                                                              • min stay varies
                                                                              • Nearest beach 0 km
                                                                              • Swimming pool
                                                                              • Child friendly

                                                                              from £200 / night

                                                                              £1,397 / week

                                                                              Book View

                                                                              from £200 / night

                                                                              Distance approx 9.62 miles from Oldsmar

                                                                                31

                                                                                Clearwater holiday apartment rental

                                                                                Florida / Clearwater

                                                                                2 7 min stay varies

                                                                                • 2 bedrooms
                                                                                • sleeps 7
                                                                                • min stay varies
                                                                                • Nearest beach 5 km
                                                                                • Swimming pool
                                                                                • Child friendly

                                                                                from £89 / night

                                                                                £621 / week

                                                                                Book View

                                                                                from £89 / night

                                                                                Distance approx 17.51 miles from Oldsmar

                                                                                  11

                                                                                  Holiday home in Port Richey

                                                                                  Florida / Port Richey

                                                                                  2 4 3 nights min

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

                                                                                  from £95 / night

                                                                                  £710 / week

                                                                                  Book View

                                                                                  from £95 / night

                                                                                  Also consider