Vacation Rentals & Villas in St. Mary Parish

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709 Houses

(4) Very Good 

    18

    Moonlight Magic! , suite on private beach Jamaica

    St. Mary Parish / Robin's Bay

    Robin's Bay villa

    1 2 3 nights min

    • 1 bedroom
    • sleeps 2
    • 3 nights min
    • Beach / lakeside relaxation
    “Peaceful Getaway” Moonlight Magic is a newly renovated room at Strawberry Fields Together! It has open views of the ocean and is surrounded by trees, grass and even a couple of hammocks. There is a kitchenette, counter space, bathroom and outdoor ba

    Price per night from

    $252

    Responds fast!
    avg. 1 hour 51 minutes

    Price per night from

    $252

      22

      Charming Cottage With Beach Access In Quiet Neighb

      St. Mary Parish / Oracabessa

      Oracabessa house

      2 4 2 nights min

      • 2 bedrooms
      • sleeps 4
      • 2 nights min
      • Nearest beach 3 mi
      • Private garden

      Price per night from

      $143

      Price per night from

      $143

        33

        Relax & Enjoy Tower Isle/Walk to the beach/AC/WIFI

        St. Mary Parish / Tower Isle

        Tower Isle house

        3 8 min stay varies

        • 3 bedrooms
        • sleeps 8
        • min stay varies
        • Nearest beach 0.5 mi
        • Child Friendly
        • Car not necessary

        Price per night from

        $63

        Responds fast!
        avg. 37 minutes

        Price per night from

        $63

          24

          Boscobel Villa w/ Ocean Views by James Bond Beach!

          St. Mary Parish / Boscobel

          Boscobel house

          3 10 3 nights min

          • 3 bedrooms
          • sleeps 10
          • 3 nights min
          • Child Friendly

          Price per night from

          $229

          Responds fast!
          avg. 33 minutes

          Price per night from

          $229

          (9) Excellent 

            35

            Grande Haven Villa - Oracabessa, St Mary Jamaica

            St. Mary Parish / Oracabessa

            Oracabessa villa

            4 8 1 night min

            • 4 bedrooms
            • sleeps 8
            • 1 night min
            • Beach / lakeside relaxation
            • Swimming pool
            • Child Friendly

            Price per night from

            $515

            Price per night from

            $515

              34

              Bolt House

              Jamaica / St. Mary Parish

              Saint Mary Parish villa

              5 10 min stay varies

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

              Price per night from

              $2,400

              Price per night from

              $2,400

                15

                Valhalla Villa

                St. Mary Parish / Boscobel

                Boscobel villa

                4 8 3 nights min

                • 4 bedrooms
                • sleeps 8
                • 3 nights min
                • Beach / lakeside relaxation
                • Nearest beach 2 mi
                • Swimming pool

                Price per night from

                $452

                Price per night from

                $452

                  18

                  The Emerald

                  St. Mary Parish / Boscobel

                  Boscobel apartment

                  2 4 3 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 3 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly

                  Price per night from

                  $92

                  Price per night from

                  $92

                  (5) Very Good 

                    19

                    Dream Maker. Private beach paradise in Jamaica.

                    St. Mary Parish / Robin's Bay

                    Robin's Bay cottage

                    1 2 3 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 3 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    “Unforgettable paradise !” It was the most wonderful vacation I've ever taken! It was literally an Unforgettable Dream! The place is truly paradisiac and I think it was the first time in my life that I could pause and enjoy the simple beauty of this pl

                    Price per night from

                    $206

                    Responds fast!
                    avg. 1 hour 51 minutes

                    Price per night from

                    $206

                      40

                      Golden Clouds

                      St. Mary Parish / Oracabessa

                      Oracabessa villa

                      8 16 min stay varies

                      • 8 bedrooms
                      • sleeps 16
                      • min stay varies
                      • Ask about children
                      • Ask about pets

                      Price per night from

                      $1,714

                      Responds fast!
                      avg. 48 minutes

                      Price per night from

                      $1,714

                        14

                        Home Away from Home 15 mins fr Ochi Rios

                        St. Mary Parish / Boscobel

                        Boscobel house

                        3 8 3 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 3 nights min
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $90

                        Responds fast!
                        avg. 49 minutes

                        Price per night from

                        $90

                          40

                          Golden Clouds

                          St. Mary Parish / Oracabessa

                          Oracabessa villa

                          9 18 min stay varies

                          • 9 bedrooms
                          • sleeps 18
                          • min stay varies
                          • Ask about children
                          • Ask about pets

                          Price per night from

                          $1,857

                          Responds fast!
                          avg. 48 minutes

                          Price per night from

                          $1,857

                          (3) Excellent 

                            49

                            Voted # 1 Seaside Villa in Ocho Rios Jamaica

                            St. Mary Parish / Oracabessa

                            Oracabessa villa

                            4 8 3 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 3 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 2 mi
                            • Swimming pool

                            Price per night from

                            $745

                            Price per night from

                            $745

                            (1) Very Good 

                              26

                              Secrets and Dreams, on private beach, Jamaica

                              St. Mary Parish / Robin's Bay

                              Robin's Bay cottage

                              1 4 1 night min

                              • 1 bedroom
                              • sleeps 4
                              • 1 night min
                              • Beach / lakeside relaxation
                              • Child Friendly

                              Price per night from

                              $246

                              Responds fast!
                              avg. 1 hour 51 minutes

                              Price per night from

                              $246

                                21

                                Quaint cottage located in the hills of Jamaica's

                                St. Mary Parish / Oracabessa

                                Oracabessa cottage

                                1 2 2 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 2 nights min

                                Price per night from

                                $52

                                Price per night from

                                $52

                                  40

                                  Golden Clouds

                                  St. Mary Parish / Oracabessa

                                  Oracabessa villa

                                  10 20 min stay varies

                                  • 10 bedrooms
                                  • sleeps 20
                                  • min stay varies
                                  • Ask about children
                                  • Ask about pets

                                  Price per night from

                                  $2,000

                                  Responds fast!
                                  avg. 48 minutes

                                  Price per night from

                                  $2,000

                                  (2) Excellent 

                                    12

                                    3 bedroom ocean view home Boscobel Jamaica / cook

                                    St. Mary Parish / Boscobel

                                    Boscobel house

                                    3 12 2 nights min

                                    • 3 bedrooms
                                    • sleeps 12
                                    • 2 nights min
                                    • Nearest beach 2 mi
                                    • Ask about children
                                    • Car not necessary

                                    Price per night from

                                    $235

                                    Price per night from

                                    $235

                                    (1) Excellent 

                                      41

                                      Sandy's Ocean View -2 bdrm - NEW- 30 mins to Ocho Rios

                                      St. Mary Parish / Port Maria

                                      Port Maria villa

                                      2 6 1 night min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 1 night min
                                      • Nearest beach 1 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $69

                                      Responds fast!
                                      avg. 2 hours 17 minutes

                                      Price per night from

                                      $69

                                      (2) Excellent 

                                        19

                                        Frankfort

                                        St. Mary Parish / Tower Isle

                                        Tower Isle villa

                                        6 12 min stay varies

                                        • 6 bedrooms
                                        • sleeps 12
                                        • min stay varies
                                        • Ask about children
                                        • Ask about pets

                                        Price per night from

                                        $3,023

                                        Responds fast!
                                        avg. 48 minutes

                                        Price per night from

                                        $3,023

                                          14

                                          High View Cottages

                                          St. Mary Parish / Oracabessa

                                          Oracabessa cottage

                                          1 2 3 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 3 nights min
                                          • Child Friendly

                                          Price per night from

                                          $58

                                          Price per night from

                                          $58

                                          (1) Excellent 

                                            40

                                            Golden Clouds

                                            St. Mary Parish / Oracabessa

                                            Oracabessa villa

                                            11 22 min stay varies

                                            • 11 bedrooms
                                            • sleeps 22
                                            • min stay varies
                                            • Ask about children
                                            • Ask about pets

                                            Price per night from

                                            $2,143

                                            Responds fast!
                                            avg. 48 minutes

                                            Price per night from

                                            $2,143

                                              20

                                              Cottage on the Ocean

                                              St. Mary Parish / Robin's Bay

                                              Robin's Bay villa

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Child Friendly

                                              Price per night from

                                              $183

                                              Price per night from

                                              $183

                                              (1) Excellent 

                                                22

                                                Two-Bedroom Seaside Condo 3

                                                St. Mary Parish / Tower Isle

                                                Tower Isle condo

                                                2 4 2 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 2 nights min
                                                • Ask about children

                                                Price per night from

                                                $252

                                                Responds fast!
                                                avg. 1 hour 37 minutes

                                                Price per night from

                                                $252

                                                (2) Average 

                                                  25

                                                  "Live Like a Jamaican"

                                                  St. Mary Parish / Tower Isle

                                                  Tower Isle house

                                                  2 4 2 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Child Friendly

                                                  Price per night from

                                                  $53

                                                  Price per night from

                                                  $53

                                                  (23) Excellent 

                                                    40

                                                    Real Jamaica - Cosy Waterfront Cottage

                                                    St. Mary Parish / Oracabessa

                                                    Oracabessa cottage

                                                    1 2 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 24 mi
                                                    “real jamaica” The team on they Property around the cotteges ist great, everybody wants you to have a good time. There are 3 cottages on the property, two cottages and the artist house. We booked the artist house, a very nice and colourful little wood-

                                                    Price per night from

                                                    $109

                                                    Price per night from

                                                    $109

                                                      40

                                                      Golden Clouds

                                                      St. Mary Parish / Oracabessa

                                                      Oracabessa villa

                                                      12 26 min stay varies

                                                      • 12 bedrooms
                                                      • sleeps 26
                                                      • min stay varies
                                                      • Ask about children
                                                      • Ask about pets

                                                      Price per night from

                                                      $2,357

                                                      Responds fast!
                                                      avg. 48 minutes

                                                      Price per night from

                                                      $2,357

                                                        40

                                                        Golden Clouds

                                                        St. Mary Parish / Oracabessa

                                                        Oracabessa villa

                                                        7 14 min stay varies

                                                        • 7 bedrooms
                                                        • sleeps 14
                                                        • min stay varies
                                                        • Ask about children
                                                        • Ask about pets

                                                        Price per night from

                                                        $1,571

                                                        Responds fast!
                                                        avg. 48 minutes

                                                        Price per night from

                                                        $1,571

                                                          4

                                                          Cool and Relaxing Getaway - 1/2/3 Bedrooms

                                                          St. Mary Parish / Tower Isle

                                                          Tower Isle apartment

                                                          3 8 2 nights min

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • 2 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $252

                                                          Price per night from

                                                          $252

                                                            15

                                                            Ian's cozy flat. 20 minutes from Ocho Rios.

                                                            St. Mary Parish / Port Maria

                                                            Port Maria apartment

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min
                                                            • Nearest beach 6 mi
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Price per night from

                                                            $46

                                                            Price per night from

                                                            $46

                                                              41

                                                              Exclusive hideaway with private pool

                                                              St. Mary Parish / Port Maria

                                                              Port Maria b and b

                                                              3 10 2 nights min

                                                              • 3 bedrooms
                                                              • sleeps 10
                                                              • 2 nights min
                                                              • Nearest beach 3 mi
                                                              • Swimming pool
                                                              • Pet Friendly

                                                              Price per night from

                                                              $745

                                                              Price per night from

                                                              $745

                                                              (1) Excellent 

                                                                18

                                                                Endless Summer (15 minutes east of Ocho Rios)

                                                                St. Mary Parish / Boscobel

                                                                Boscobel villa

                                                                2 4 1 night min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 1 night min
                                                                • Swimming pool
                                                                • Air conditioning

                                                                Price per night from

                                                                $183

                                                                Price per night from

                                                                $183

                                                                  14

                                                                  Private Chalet Ocho Rios

                                                                  St. Mary Parish / Tower Isle

                                                                  Tower Isle chalet

                                                                  2 2 nights min

                                                                  • sleeps 2
                                                                  • 2 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 5 mi
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $33

                                                                  Price per night from

                                                                  $33

                                                                    40

                                                                    Golden Clouds

                                                                    St. Mary Parish / Oracabessa

                                                                    Oracabessa villa

                                                                    12 24 min stay varies

                                                                    • 12 bedrooms
                                                                    • sleeps 24
                                                                    • min stay varies
                                                                    • Ask about children
                                                                    • Ask about pets

                                                                    Price per night from

                                                                    $2,286

                                                                    Responds fast!
                                                                    avg. 48 minutes

                                                                    Price per night from

                                                                    $2,286

                                                                    (2) Excellent 

                                                                      33

                                                                      Northcoast Jamaica Paradise, Private beach,pool

                                                                      St. Mary Parish / Oracabessa

                                                                      Oracabessa villa

                                                                      3 8 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 2 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Car not necessary

                                                                      Price per night from

                                                                      $229

                                                                      Price per night from

                                                                      $229

                                                                      (1) Excellent 

                                                                        38

                                                                        Seaside Villa in Boscobel, St. Mary

                                                                        St. Mary Parish / Boscobel

                                                                        Boscobel villa

                                                                        6 12 3 nights min

                                                                        • 6 bedrooms
                                                                        • sleeps 12
                                                                        • 3 nights min
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $687

                                                                        Responds fast!
                                                                        avg. 1 hour 37 minutes

                                                                        Price per night from

                                                                        $687

                                                                        (2) Excellent 

                                                                          28

                                                                          Oceanfront Condo, Pebble Beach, Large Sundeck with Ocean Access!

                                                                          St. Mary Parish / Tower Isle

                                                                          Tower Isle condo

                                                                          2 4 2 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 2 nights min
                                                                          • Nearest beach 0.1 mi
                                                                          • Swimming pool
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $275

                                                                          Responds fast!
                                                                          avg. 3 hours 45 minutes

                                                                          Price per night from

                                                                          $275

                                                                            28

                                                                            Blow Hole - Oracabessa 5 Bedrooms

                                                                            St. Mary Parish / Oracabessa

                                                                            Oracabessa house

                                                                            5 10 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 10
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $785

                                                                            Price per night from

                                                                            $785

                                                                              9

                                                                              Sajeres Villa

                                                                              St. Mary Parish / Boscobel

                                                                              Boscobel villa

                                                                              2 4 2 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 2 nights min
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $52

                                                                              Price per night from

                                                                              $52