Villas in Portland Parish and Houses – Holiday Lettings - Holiday Rentals Portland Parish

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165 Holiday homes

    15

    Holiday apartment rental

    Portland Parish / Buff Bay

    2 4 3 nights min

    • 2 bedrooms
    • sleeps 4
    • 3 nights min
    • Child friendly
    • Private garden

    from £40 / night

    £281 / week

    Book View

    from £40 / night

      12

      Holiday home rental

      Portland Parish / Port Antonio

      4 9 2 nights min

      • 4 bedrooms
      • sleeps 9
      • 2 nights min
      • Nearest beach 1 km
      • Child friendly
      • Car not necessary

      from £18 / night

      £133 - £1,366 / week

      Book View

      from £18 / night

      (30) Excellent 

        11

        Portland Parish holiday villa accommodation

        Portland Parish / Port Antonio

        2 5 4 nights min

        • 2 bedrooms
        • sleeps 5
        • 4 nights min
        • Beach / lakeside relaxation
        • Nearest beach 1 km
        • Swimming pool
        “Jamaica jewel!” We adored our stay at Tranquility -- it truly lives up to its name! This elegant, old-school school villa, built in the 1950s, is perched on a mountaintop. The views alone (Port antonio bay one one side, Blue Mountains on the other) are worth the price of admission! The house is small (5 people max but 4 is ideal) but airy and completely private. And the decor -- white wood wainscoting, ceiling fans, teak floors and simple white beds with mosquito netting -- is classic Jamaica (Noel Coward or Ian Fleming would have been very much at home here). Our stay was made even more delightful by a warm and professional staff: Beverly, a gifted cook specializing in Jamaican cuisine, on-property houseman Dennis, and on-call driver Charlie. Frenchman's Cove, a gorgeous private beach, is a 15-20 minute car ride away -- but truthfully, this is the kind of place where you can wile away the hours sitting by the pool and watching the changing views as the light shifts. One issue to take into consideration: the trip from the airport is 2- 21/2 hours through winding mountain roads. But the setting and staff make it well worth the wait!

        from £234 / night

        £1,636 / week

        Book View

        from £234 / night

        (14) Excellent 

          29

          Holiday home in Portland Parish

          Port Antonio / Blue Lagoon, Port Antonio

          4 9 1 night min

          • 4 bedrooms
          • sleeps 9
          • 1 night min
          • Beach / lakeside relaxation
          • Suitable for children age 5+
          • Car not necessary

          from £177 / night

          £926 - £969 / week

          Book View

          Responds fast!
          avg. 2 hours 59 minutes

          from £177 / night

          (2)  

            27

            Holiday guest house in Portland Parish

            Portland Parish / Long Bay

            5 8 2 nights min

            • 5 bedrooms
            • sleeps 8
            • 2 nights min
            • Beach / lakeside relaxation
            • Child friendly
            • Car not necessary

            from £53 / night

            £353 / week

            Book View

            from £53 / night

              16

              Holiday villa with golf nearby in Port Antonio

              Port Antonio / Blue Lagoon, Port Antonio

              4 8 3 nights min

              • 4 bedrooms
              • sleeps 8
              • 3 nights min
              • Beach / lakeside relaxation
              • Suitable for children age 5+
              • Air conditioning

              from £1,147 / night

              £7,935 / week

              Book View

              from £1,147 / night

                15

                Holiday guest house in Portland Parish

                Portland Parish / Long Bay

                1 3 2 nights min

                • 1 bedroom
                • sleeps 3
                • 2 nights min
                • Nearest beach 0 km
                • Child friendly
                • Car not necessary

                from £80 / night

                £556 / week

                Book View

                from £80 / night

                (1) Excellent 

                  12

                  Holiday guest house rental

                  Portland Parish / Long Bay

                  1 3 2 nights min

                  • 1 bedroom
                  • sleeps 3
                  • 2 nights min
                  • Nearest beach 0 km
                  • Child friendly
                  • Car not necessary

                  from £62 / night

                  £432 / week

                  Book View

                  from £62 / night

                    4

                    Villa rental in Portland Parish

                    Portland Parish / Long Bay

                    4 8 1 night min

                    • 4 bedrooms
                    • sleeps 8
                    • 1 night min
                    • Beach / lakeside relaxation
                    • Nearest beach 0.1 km
                    • Child friendly

                    from £40 / night

                    £247 - £1,358 / week

                    Book View

                    from £40 / night

                      12

                      Holiday guest house in Portland Parish

                      Portland Parish / Long Bay

                      1 2 2 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 2 nights min
                      • Nearest beach 0 km
                      • Child friendly
                      • Car not necessary

                      from £40 / night

                      £278 / week

                      Book View

                      from £40 / night

                      (1) Excellent 

                        29

                        Villa rental in Portland Parish

                        Port Antonio / Williamsfield

                        2 6 2 nights min

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

                        from £309 / night

                        £1,763 / week

                        Book View

                        from £309 / night

                          38

                          Holiday villa in Portland Parish

                          Portland Parish / Port Antonio

                          1 3 1 night min

                          • 1 bedroom
                          • sleeps 3
                          • 1 night min
                          • Child friendly
                          • Car not necessary
                          • Air conditioning

                          from £71 / night

                          £445 / week

                          Book View

                          from £71 / night

                            12

                            Portland Parish holiday cottage rental

                            Portland Parish / Long Bay

                            1 2 1 night min

                            • 1 bedroom
                            • sleeps 2
                            • 1 night min
                            • Nearest beach 0 km
                            • Child friendly
                            • Private garden

                            from £49 / night

                            £340 / week

                            Book View

                            from £49 / night

                            (1) Excellent 

                              33

                              Portland Parish holiday villa rental

                              Portland Parish / Port Antonio

                              1 2 1 night min

                              • 1 bedroom
                              • sleeps 2
                              • 1 night min
                              • Child friendly
                              • Car not necessary

                              from £77 / night

                              £334 / week

                              Book View

                              from £77 / night

                                15

                                Guest house rental in Portland Parish

                                Portland Parish / Long Bay

                                3 10 2 nights min

                                • 3 bedrooms
                                • sleeps 10
                                • 2 nights min
                                • Nearest beach 0 km
                                • Child friendly
                                • Car not necessary

                                from £265 / night

                                £1,323 / week

                                Book View

                                from £265 / night

                                  32

                                  Holiday villa in Port Antonio

                                  Portland Parish / Port Antonio

                                  1 2 1 night min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 1 night min
                                  • Child friendly
                                  • Car not necessary

                                  from £53 / night

                                  £334 / week

                                  Book View

                                  from £53 / night

                                    7

                                    Holiday apartment rental

                                    Portland Parish / Port Antonio

                                    1 6 1 night min

                                    • 1 bedroom
                                    • sleeps 6
                                    • 1 night min
                                    • Child friendly

                                    from £35 / night

                                    £241 / week

                                    Book View

                                    from £35 / night

                                      33

                                      Holiday villa rental

                                      Portland Parish / Port Antonio

                                      1 3 1 night min

                                      • 1 bedroom
                                      • sleeps 3
                                      • 1 night min
                                      • Child friendly
                                      • Car not necessary
                                      • Air conditioning

                                      from £71 / night

                                      £445 / week

                                      Book View

                                      from £71 / night

                                      (2) Very Good 

                                        111

                                        Villa rental in Port Antonio with golf nearby

                                        Portland Parish / Port Antonio

                                        4 10 1 night min

                                        • 4 bedrooms
                                        • sleeps 10
                                        • 1 night min
                                        • Nearest beach 2 km
                                        • Child friendly
                                        • Car not necessary

                                        from £221 / night

                                        £1,401 / week

                                        Book View

                                        from £221 / night

                                          24

                                          Holiday home in Portland Parish

                                          Portland Parish / Manchioneal

                                          4 10 3 nights min

                                          • 4 bedrooms
                                          • sleeps 10
                                          • 3 nights min
                                          • Nearest beach 1 km
                                          • Child friendly
                                          • Air conditioning

                                          from £221 / night

                                          £1,543 / week

                                          Book View

                                          from £221 / night

                                          (5) Very Good 

                                            14

                                            Holiday log cabin in Portland Parish

                                            Portland Parish / Port Antonio

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Nearest beach 16 km
                                            • Swimming pool
                                            • Child friendly

                                            from £44 / night

                                            £265 / week

                                            Book View

                                            from £44 / night

                                              56

                                              Portland Parish holiday apartment rental

                                              Portland Parish / Long Bay

                                              2 4 1 night min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 1 night min
                                              • Child friendly
                                              • Car not necessary
                                              • Private garden

                                              from £27 / night

                                              £133 - £318 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 46 minutes

                                              from £27 / night

                                              (39) Very Good 

                                                38

                                                Holiday cottage in Portland Parish

                                                Portland Parish / Port Antonio

                                                2 4 2 nights min

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

                                                from £44 / night

                                                £309 / week

                                                Book View

                                                Responds fast!
                                                avg. 3 hours 32 minutes

                                                from £44 / night

                                                (5) Excellent 

                                                  15

                                                  Holiday home with swimming pool in Portland Parish

                                                  Portland Parish / Port Antonio

                                                  4 10 3 nights min

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • 3 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 1 km
                                                  • Swimming pool

                                                  from £525 / night

                                                  £3,671 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 24 minutes

                                                  from £525 / night

                                                  (1) Excellent 

                                                    40

                                                    Holiday home with golf nearby in Portland Parish

                                                    Portland Parish / Boston Bay

                                                    2 4 1 night min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 1 night min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 km
                                                    • Child friendly

                                                    from £58 / night

                                                    £388 / week

                                                    Book View

                                                    from £58 / night

                                                      11

                                                      Holiday home in Portland Parish

                                                      Portland Parish / Port Antonio

                                                      4 10 1 night min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 1 night min
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £16 / night

                                                      £106 / week

                                                      Book View

                                                      from £16 / night

                                                      (1) Excellent 

                                                        15

                                                        Holiday log cabin in Port Antonio

                                                        Portland Parish / Port Antonio

                                                        1 2 1 night min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 1 night min
                                                        • Nearest beach 16 km
                                                        • Swimming pool
                                                        • Child friendly

                                                        from £27 / night

                                                        £176 / week

                                                        Book View

                                                        from £27 / night

                                                          30

                                                          Home rental in Portland Parish

                                                          Port Antonio / Blue Lagoon, Port Antonio

                                                          4 8 2 nights min

                                                          • 4 bedrooms
                                                          • sleeps 8
                                                          • 2 nights min
                                                          • Beach / lakeside relaxation
                                                          • Child friendly
                                                          • Air conditioning

                                                          from £106 / night

                                                          £750 - £2,230 / week

                                                          Book View

                                                          from £106 / night

                                                            16

                                                            Portland Parish holiday condo rental

                                                            Portland Parish / Port Antonio

                                                            2 4 1 night min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 1 night min
                                                            • Beach / lakeside relaxation
                                                            • Child friendly
                                                            • Car not necessary

                                                            from £89 / night

                                                            £618 / week

                                                            Book View

                                                            from £89 / night

                                                              13

                                                              Holiday villa in Portland Parish

                                                              Jamaica / Portland Parish

                                                              1 2 2 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 2 nights min
                                                              • Child friendly
                                                              • Pet friendly

                                                              from £221 / night

                                                              £1,543 / week

                                                              Book View

                                                              from £221 / night

                                                              (3) Excellent 

                                                                81

                                                                Villa rental in Portland Parish

                                                                Portland Parish / Port Antonio

                                                                3 8 1 night min

                                                                • 3 bedrooms
                                                                • sleeps 8
                                                                • 1 night min
                                                                • Child friendly
                                                                • Private garden

                                                                from £66 / night

                                                                £463 - £710 / week

                                                                Book View

                                                                from £66 / night

                                                                (4) Excellent 

                                                                  39

                                                                  Holiday home in Portland Parish

                                                                  Portland Parish / Port Antonio

                                                                  2 4 2 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 2 nights min
                                                                  • Nearest beach 2 km
                                                                  • Car not necessary
                                                                  • Private garden

                                                                  from £49 / night

                                                                  £340 - £710 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 44 minutes

                                                                  from £49 / night

                                                                    18

                                                                    Holiday home in Port Antonio

                                                                    Portland Parish / Port Antonio

                                                                    3 6 2 nights min

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

                                                                    from £67 / night

                                                                    £463 - £1,080 / week

                                                                    Book View

                                                                    from £67 / night

                                                                      26

                                                                      Portland Parish holiday b&b rental

                                                                      Portland Parish / Port Antonio

                                                                      1 2 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 2 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Suitable for children age 5+
                                                                      • Ask about pets

                                                                      from £53 / night

                                                                      £309 / week

                                                                      Book View

                                                                      from £53 / night

                                                                      (35) Excellent 

                                                                        34

                                                                        Villa rental in Port Antonio with swimming pool

                                                                        Portland Parish / Port Antonio

                                                                        2 5 4 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • 4 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 2 km
                                                                        • Swimming pool
                                                                        “Jamaica jewel!” We adored our stay at Tranquility -- it truly lives up to its name! This elegant, old-school school villa, built in the 1950s, is perched on a mountaintop. The views alone (Port antonio bay one one side, Blue Mountains on the other) are worth the price of admission! The house is small (5 people max but 4 is ideal) but airy and completely private. And the decor -- white wood wainscoting, ceiling fans, teak floors and simple white beds with mosquito netting -- is classic Jamaica (Noel Coward or Ian Fleming would have been very much at home here). Our stay was made even more delightful by a warm and professional staff: Beverly, a gifted cook specializing in Jamaican cuisine, on-property houseman Dennis, and on-call driver Charlie. Frenchman's Cove, a gorgeous private beach, is a 15-20 minute car ride away -- but truthfully, this is the kind of place where you can wile away the hours sitting by the pool and watching the changing views as the light shifts. One issue to take into consideration: the trip from the airport is 2- 21/2 hours through winding mountain roads. But the setting and staff make it well worth the wait!

                                                                        from £243 / night

                                                                        £1,587 - £2,050 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 32 minutes

                                                                        from £243 / night

                                                                          11

                                                                          Port Antonio holiday home rental

                                                                          Portland Parish / Port Antonio

                                                                          1 4 1 night min

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • 1 night min
                                                                          • Child friendly
                                                                          • Ask about pets

                                                                          from £67 / night

                                                                          £432 / week

                                                                          Book View

                                                                          from £67 / night

                                                                          (3) Very Good 

                                                                            28

                                                                            Holiday home in Portland Parish

                                                                            Portland Parish / Port Antonio

                                                                            1 4 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 3 nights min
                                                                            • Child friendly
                                                                            • Private garden

                                                                            from £67 / night

                                                                            £463 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 47 minutes

                                                                            from £67 / night

                                                                            (1)  

                                                                              16

                                                                              Portland Parish holiday home rental

                                                                              Portland Parish / Port Antonio

                                                                              6 12 min stay varies

                                                                              • 6 bedrooms
                                                                              • sleeps 12
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Swimming pool
                                                                              • Ask owner if suitable for children

                                                                              from £1,155 / night

                                                                              £8,083 - £9,237 / week

                                                                              Enquire View

                                                                              from £1,155 / night

                                                                              (7) Excellent 

                                                                                22

                                                                                Port Antonio holiday guest house rental

                                                                                Portland Parish / Port Antonio

                                                                                6 8 3 nights min

                                                                                • 6 bedrooms
                                                                                • sleeps 8
                                                                                • 3 nights min
                                                                                • Nearest beach 1 km
                                                                                • Child friendly
                                                                                • Car not necessary

                                                                                from £133 / night

                                                                                £926 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 53 minutes

                                                                                from £133 / night

                                                                                  18

                                                                                  Holiday home in Portland Parish

                                                                                  Portland Parish / Port Antonio

                                                                                  4 8 min stay varies

                                                                                  • 4 bedrooms
                                                                                  • sleeps 8
                                                                                  • min stay varies
                                                                                  • Beach / lakeside relaxation
                                                                                  • Ask owner if suitable for children

                                                                                  from £770 / night

                                                                                  £5,388 - £6,158 / week

                                                                                  Enquire View

                                                                                  from £770 / night

                                                                                  Top Destination reviews

                                                                                  Mr Barrys - Portland
                                                                                  Harmony Heights

                                                                                  As a Jamaican descendent, I have been a regular visitor to Jamaica, for over 20 years, however my stay at Harmony Heights, was in fact the most relaxing stress free, and truely Irie (no problem) stay I have ever experienced while in Jamaica. I felt as if I was home from home, I was traveling with my teenage daughter, we were safe comfortable and our belongings secure, all of which were priority. The Local area has a relaxed, welcoming and friendly ambiance, the local beaches are in walking distance and are all distinctively unique, there are local shops and eateries. If you are seeking retreat or sanctuary this is the place to be, with the best of everything, near enough to the local town, beautiful panoramic views, nestled in the lush foliage of Fairy Hill, which did occasionally boast some rare sightings of local birdlife. The facilitator at Harmony Heights is called "Head" he is always at hand to assist if needs be. Authentic Jamaican meals can be provided for a reasonable charge, which was great because we had a daily choice of self catering or not. The Kitchen and all amenities are sufficient.see more

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