Vacation Rentals with Pool in Montego Bay

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Filtering by: Swimming pool

421 vacation rentals
    22

    Anticipation - Tryall Club

    Montego Bay / Hopewell

    Hopewell villa

    6 12 min stay varies

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

    Price per night from

    $2,241

    Price per night from

    $2,241

      13

      Sundance - Tryall Club

      Montego Bay / Hopewell

      Hopewell villa

      5 10 min stay varies

      • 5 bedrooms
      • sleeps 10
      • min stay varies
      • Swimming pool

      Price per night from

      $3,143

      Price per night from

      $3,143

        14

        Karma Bay - Tryall Club

        Montego Bay / Hopewell

        Hopewell villa

        6 12 min stay varies

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

        Price per night from

        $2,214

        Price per night from

        $2,214

        (5) Very Good 

          14

          Beach Studio with European Country Charm 15 Minute

          Montego Bay / Rose Hall

          Rose Hall apartment

          1 2 2 nights min

          • 1 bedroom
          • sleeps 2
          • 2 nights min
          • Beach / lakeside relaxation
          • Swimming pool
          • Child Friendly

          Price per night from

          $81

          Price per night from

          $81

          (7) Very Good 

          Certificate of Excellence

            44

            Nautical Homes Miramar

            St. James Parish / Montego Bay

            Montego Bay house

            3 6 3 nights min

            • 3 bedrooms
            • sleeps 6
            • 3 nights min
            • Beach / lakeside relaxation
            • Nearest beach 2 mi
            • Swimming pool
            “Holiday Home” My daughter and I rented this really beautiful villa. Angie collected us from the airport and kindly took us shopping to get some food to tide us over until we picked up our rented car. The house smelled fresh as we walked in. The lounge
            …see more

            Certificate of Excellence

            Price per night from

            $338

            Responds fast!
            avg. 30 minutes

            Price per night from

            $338

            (6) Excellent 

              26

              Village Maria~ A true Jamaican villa experience Beachfront

              St. James Parish / Montego Bay

              Montego Bay house

              4 8 min stay varies

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

              Price per night from

              $744

              Responds fast!
              avg. 29 minutes

              Price per night from

              $744

                17

                Infinity - Tryall Club

                Montego Bay / Hopewell

                Hopewell villa

                5 10 min stay varies

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

                Price per night from

                $2,091

                Price per night from

                $2,091

                  27

                  Penthouse In Paradise, 3 bdrm incl. housekeeper

                  St. James Parish / Montego Bay

                  Montego Bay apartment

                  3 6 1 night min

                  • 3 bedrooms
                  • sleeps 6
                  • 1 night min
                  • Beach / lakeside relaxation
                  • Nearest beach 0.5 mi
                  • Swimming pool

                  Price per night from

                  $373

                  Responds fast!
                  avg. 2 hours 44 minutes

                  Price per night from

                  $373

                  (5) Excellent 

                    26

                    Gorgeous Oceanview Condo Montego Bay Jamaica

                    St. James Parish / Montego Bay

                    Montego Bay apartment

                    2 4 3 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 3 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0 mi
                    • Swimming pool
                    “A great place to stay!” We spent three wonderful days at alyssa's Condo in the heart of Montego Bay. It is in a quiet, gated community, with a 1 minute walk to Doctor's Cave beach. What more could you ask for? The condo is clean, and everything sta
                    …see more

                    Price per night from

                    $331

                    Price per night from

                    $331

                    (2) Very Good 

                      29

                      2-br watervu apt-Seawind onthe Bay,Montego Bay,Jam

                      St. James Parish / Montego Bay

                      Montego Bay apartment

                      2 5 1 night min

                      • 2 bedrooms
                      • sleeps 5
                      • 1 night min
                      • Beach / lakeside relaxation
                      • Nearest beach 0 mi
                      • Swimming pool

                      Price per night from

                      $201

                      Price per night from

                      $201

                        20

                        Twin Palms - Tryall Club

                        Montego Bay / Hopewell

                        Hopewell villa

                        7 14 7 nights min

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

                        Price per night from

                        $3,507

                        Price per night from

                        $3,507

                        (3) Very Good 

                          20

                          Pleasant View Villa

                          Montego Bay / Hopewell

                          Hopewell house

                          3 6 3 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 8 mi
                          • Swimming pool

                          Price per night from

                          $319

                          Responds fast!
                          avg. 2 hours 20 minutes

                          Price per night from

                          $319

                            26

                            Allamanda

                            St. James Parish / Montego Bay

                            Montego Bay villa

                            5 12 5 nights min

                            • 5 bedrooms
                            • sleeps 12
                            • 5 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $1,286

                            Price per night from

                            $1,286

                              18

                              Hummingbird House - Tryall Club

                              Montego Bay / Hopewell

                              Hopewell villa

                              7 14 min stay varies

                              • 7 bedrooms
                              • sleeps 14
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $3,143

                              Price per night from

                              $3,143

                                26

                                Knockando

                                Montego Bay / Hopewell

                                Hopewell villa

                                5 13 min stay varies

                                • 5 bedrooms
                                • sleeps 13
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $1,257

                                Price per night from

                                $1,257

                                  12

                                  Palmyra 1 Bedroom Condo

                                  Montego Bay / Rose Hall

                                  Rose Hall condo

                                  1 2 1 night min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 1 night min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $195

                                  Price per night from

                                  $195

                                  (5) Very Good 

                                    16

                                    Paradise Plum - 4BD,Pool, Ocean views, full staff

                                    Montego Bay / Rose Hall

                                    Rose Hall house

                                    4 10 min stay varies

                                    • 4 bedrooms
                                    • sleeps 10
                                    • min stay varies
                                    • Nearest beach 2 mi
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $859

                                    Responds fast!
                                    avg. 3 hours 56 minutes

                                    Price per night from

                                    $859

                                    (10) Very Good 

                                      41

                                      Ocean Front Montego Bay Club Apartments

                                      St. James Parish / Montego Bay

                                      Montego Bay apartment

                                      1 4 min stay varies

                                      • 1 bedroom
                                      • sleeps 4
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0 mi
                                      • Swimming pool

                                      Price per night from

                                      $148

                                      Responds fast!
                                      avg. 1 hour 37 minutes

                                      Price per night from

                                      $148

                                      (14) Excellent 

                                        29

                                        2 bed/ 2.5 bath Ocean Front Condo Montego Bay Club

                                        St. James Parish / Montego Bay

                                        Montego Bay condo

                                        2 8 min stay varies

                                        • 2 bedrooms
                                        • sleeps 8
                                        • min stay varies
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0.1 mi
                                        • Swimming pool

                                        Price per night from

                                        $217

                                        Responds fast!
                                        avg. 1 hour 37 minutes

                                        Price per night from

                                        $217

                                        (18) Very Good 

                                          6

                                          Private Beachfront Condos in Montego Bay Jamaica

                                          Montego Bay / Rose Hall

                                          Rose Hall apartment

                                          1 4 2 nights min

                                          • 1 bedroom
                                          • sleeps 4
                                          • 2 nights min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Air conditioning
                                          “I will go back anytime” Before our departure, the booking was very professional. Debra advised us well, and she was very patient with us. On our arrival, we were greeted by Karen as if we were family returned to the country for a long absence. We had
                                          …see more

                                          Price per night from

                                          $97

                                          Responds fast!
                                          avg. 3 hours 32 minutes

                                          Price per night from

                                          $97

                                          (1) Excellent 

                                            15

                                            Overlook - Tryall Club

                                            Montego Bay / Hopewell

                                            Hopewell villa

                                            5 10 min stay varies

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

                                            Price per night from

                                            $1,558

                                            Price per night from

                                            $1,558

                                              10

                                              Villa Donna Sea peak Suite

                                              Montego Bay / Ironshore

                                              Ironshore apartment

                                              1 4 1 night min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 1 night min
                                              • Swimming pool
                                              • Air conditioning

                                              Price per night from

                                              $86

                                              Price per night from

                                              $86

                                                47

                                                gRAND LUXURY! STAFFED! POOL! CHEF! FAMILY FRIENDLY-Georgian House- 5BR

                                                Montego Bay / Rose Hall

                                                Rose Hall villa

                                                5 12 min stay varies

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

                                                Price per night from

                                                $1,143

                                                Price per night from

                                                $1,143

                                                  19

                                                  Ocean View Retreat

                                                  Montego Bay / Ironshore

                                                  Ironshore villa

                                                  2 6 3 nights min

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

                                                  Price per night from

                                                  $332

                                                  Price per night from

                                                  $332

                                                    46

                                                    GRAND LUXURY! STAFF! CHEF! VIEWS! POOL!Georgian House, Montego Bay 4BR

                                                    Montego Bay / Rose Hall

                                                    Rose Hall villa

                                                    4 8 min stay varies

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

                                                    Price per night from

                                                    $1,082

                                                    Price per night from

                                                    $1,082

                                                      11

                                                      BREATH-TAKING JAMAICAN PARADISE

                                                      Montego Bay / Rose Hall

                                                      Rose Hall villa

                                                      3 6 2 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 2 nights min
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $178

                                                      Price per night from

                                                      $178

                                                      (3) Excellent 

                                                        27

                                                        Ocean Front Modern Studio Hip Strip Beach Mobay

                                                        St. James Parish / Montego Bay

                                                        Montego Bay condo

                                                        1 4 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Nearest beach 0 mi
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $148

                                                        Responds fast!
                                                        avg. 1 hour 37 minutes

                                                        Price per night from

                                                        $148

                                                          52

                                                          LUXURY! POOL! GATED COMMUMITY! STAFF!Georgian House, Montego Bay 7BR

                                                          Montego Bay / Rose Hall

                                                          Rose Hall villa

                                                          7 16 min stay varies

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

                                                          Price per night from

                                                          $1,203

                                                          Price per night from

                                                          $1,203

                                                          (6) Excellent 

                                                          Certificate of Excellence

                                                            38

                                                            Seawind Studio - Montego Freeport, Montego Bay

                                                            St. James Parish / Montego Bay

                                                            Montego Bay studio

                                                            Studio 4 3 nights min

                                                            • Studio
                                                            • sleeps 4
                                                            • 3 nights min
                                                            • Nearest beach 0.2 mi
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Traveler” First i would like to thank the owner Petrinia Brooks for such a warm reception on arrival. The appartment should be described as a hidden treasure for travelers who is looking for R/R. The pictures are true reflection of what the appartment
                                                            …see more

                                                            Certificate of Excellence

                                                            Price per night from

                                                            $98

                                                            Responds fast!
                                                            avg. 38 minutes

                                                            Price per night from

                                                            $98

                                                            (2) Excellent 

                                                              47

                                                              TWIN PALMS RETREAT - MONTEGO BAY JAMAICA

                                                              St. James Parish / Montego Bay

                                                              Montego Bay townhouse

                                                              3 6 3 nights min

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

                                                              Price per night from

                                                              $413

                                                              Responds fast!
                                                              avg. 1 hour 33 minutes

                                                              Price per night from

                                                              $413

                                                                12

                                                                Reef House - Tryall Club

                                                                Montego Bay / Hopewell

                                                                Hopewell villa

                                                                4 8 min stay varies

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

                                                                Price per night from

                                                                $857

                                                                Price per night from

                                                                $857

                                                                (8) Very Good 

                                                                  41

                                                                  Gorgeous 14 Flr Ocean Front Studio

                                                                  St. James Parish / Montego Bay

                                                                  Montego Bay apartment

                                                                  3 2 nights min

                                                                  • sleeps 3
                                                                  • 2 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 5 mi
                                                                  • Swimming pool
                                                                  “Awesome” What an amazing place the condo has the best view in Montego bay it was better then we thought, the shop down in the building is very handy. The condo has everything one needs. Jacque was very helpful with all the info. We would have stayed l
                                                                  …see more

                                                                  Price per night from

                                                                  $92

                                                                  Price per night from

                                                                  $92

                                                                    17

                                                                    Avalon - Tryall Club

                                                                    Montego Bay / Hopewell

                                                                    Hopewell villa

                                                                    4 8 min stay varies

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

                                                                    Price per night from

                                                                    $786

                                                                    Price per night from

                                                                    $786

                                                                    (2) Excellent 

                                                                      32

                                                                      Windfall Villas... FREE TRANSPORTATION !

                                                                      Montego Bay / St James, Montego Bay

                                                                      St James, Montego Bay villa

                                                                      3 6 1 night min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 1 night min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 4 mi
                                                                      • Swimming pool

                                                                      Price per night from

                                                                      $344

                                                                      Price per night from

                                                                      $344

                                                                      (3) Excellent 

                                                                        37

                                                                        Montego Studio at Seawind on the Bay with beach access - Freeport, Montego Bay

                                                                        St. James Parish / Montego Bay

                                                                        Montego Bay studio

                                                                        Studio 4 min stay varies

                                                                        • Studio
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Nearest beach 0.1 mi
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $86

                                                                        Responds fast!
                                                                        avg. 38 minutes

                                                                        Price per night from

                                                                        $86

                                                                        (10) Very Good 

                                                                          42

                                                                          Caribbean Soul your island home

                                                                          Montego Bay / St James, Montego Bay

                                                                          St James, Montego Bay condo

                                                                          1 3 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 3
                                                                          • 3 nights min
                                                                          • Swimming pool
                                                                          • Air conditioning
                                                                          • Private garden

                                                                          Price per night from

                                                                          $144

                                                                          Responds fast!
                                                                          avg. 2 hours 34 minutes

                                                                          Price per night from

                                                                          $144

                                                                            16

                                                                            Sea View Queen Room in Luxury Villa

                                                                            Montego Bay / Ironshore

                                                                            Ironshore villa

                                                                            1 2 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 2 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 0.6 mi
                                                                            • Swimming pool

                                                                            Price per night from

                                                                            $247

                                                                            Responds fast!
                                                                            avg. 3 hours 51 minutes

                                                                            Price per night from

                                                                            $247

                                                                            (21) Very Good 

                                                                              12

                                                                              Beautiful ocean views, Montego Bay Studio near Doctors Cave Beach and Hip Strip

                                                                              St. James Parish / Montego Bay

                                                                              Montego Bay apartment

                                                                              1 2 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 2 nights min
                                                                              • Nearest beach 0.5 mi
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              “Vacation at Montego Bay Studio apt. 35a” We surely did enjoy our stay at No 35a. Initially we had made arrangements for a stay of one week at No 35a in Montego Bay and one week at another Hotel in Kingston. After our first two days at No. 35a we did
                                                                              …see more

                                                                              Price per night from

                                                                              $81

                                                                              Price per night from

                                                                              $81