Vacation Rentals with Pool in Jamaica

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Filtering by: Swimming pool

1,269 vacation rentals
    14

    The Marley manor

    Kingston Parish / Kingston

    Kingston apartment

    2 4 min stay varies

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

    Price per night from

    $149

    Price per night from

    $149

    (2) Very Good 

      19

      Sun Kissed - Rio Bueno 4 Bedroom Beachfront

      St. Ann Parish / Discovery Bay

      Discovery Bay house

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Beach / lakeside relaxation
      • Swimming pool
      • Ask about children

      Price per night from

      $781

      Price per night from

      $781

      (2) Excellent 

        25

        Seagrapes - Jamaica

        St. Ann Parish / Discovery Bay

        Discovery Bay villa

        6 10 min stay varies

        • 6 bedrooms
        • sleeps 10
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning
        “Dream Vacation” We had a marvelous, fun-filled, and restful vacation in at Sea Grapes Everyone in our party was a little bit heartbroken when we had to go home I think! The accomadations were all that we had hoped for and the property and views were b

        Price per night from

        $1,086

        Price per night from

        $1,086

          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

            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

            (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

              $514

              Price per night from

              $514

              (14) Excellent 

                14

                Riviera Wellness Retreat, Mammee Bay villa, JM

                St. Ann Parish / Mammee Bay

                Mammee Bay villa

                3 6 1 night min

                • 3 bedrooms
                • sleeps 6
                • 1 night min
                • Beach / lakeside relaxation
                • Swimming pool
                • Child Friendly
                “Riviera Villa is like living in paradise with beautiful people.” My party and I have been visiting our holiday home as we like to call it for the last 13 years. In recent years we have gone twice. The staff have become apart of our own family. Need l

                Price per night from

                $287

                Price per night from

                $287

                (4) Excellent 

                  22

                  Sugar Bay - Jamaica

                  St. Ann Parish / Discovery Bay

                  Discovery Bay villa

                  5 10 7 nights min

                  • 5 bedrooms
                  • sleeps 10
                  • 7 nights min
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning
                  “Sugar Bay” I have been to Sugar Bay twice with my all girls tennis and bridge group. Sugar Bay is a gorgeous, upscale villa where you feel right at home! Reds, the wonderful houseman, is a delight and makes sure you have everything you need. The cook

                  Price per night from

                  $2,032

                  Price per night from

                  $2,032

                  (5) Excellent 

                    10

                    Pelican Three Bedroom Villa

                    Saint Elizabeth Parish / Treasure Beach

                    Treasure Beach villa

                    3 6 2 nights min

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

                    Price per night from

                    $567

                    Price per night from

                    $567

                    (2) Excellent 

                      35

                      The Artiste's Boutique by Bohemian Lodges

                      Kingston Parish / Kingston

                      Kingston house

                      5 11 min stay varies

                      • 5 bedrooms
                      • sleeps 11
                      • min stay varies
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $212

                      Price per night from

                      $212

                      (2) Very Good 

                        13

                        Sunrise Supreme

                        St. Ann Parish / Runaway Bay

                        Runaway Bay apartment

                        1 2 2 nights min

                        • 1 bedroom
                        • sleeps 2
                        • 2 nights min
                        • Nearest beach 5 mi
                        • Swimming pool
                        • Child Friendly

                        Price per night from

                        $60

                        Price per night from

                        $60

                        (1) Excellent 

                          37

                          Spanish Cove

                          Jamaica / St. Ann Parish

                          Saint Ann Parish villa

                          4 8 min stay varies

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

                          Price per night from

                          $880

                          Price per night from

                          $880

                            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

                            $451

                            Price per night from

                            $451

                            (9) Excellent 

                              10

                              77 West Boutique Hotel (Cottage 1 of 5)

                              Saint Elizabeth Parish / Treasure Beach

                              Treasure Beach cottage

                              1 2 1 night min

                              • 1 bedroom
                              • sleeps 2
                              • 1 night min
                              • Nearest beach 0 mi
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $149

                              Price per night from

                              $149

                              (12) Excellent 

                                7

                                Seadrift Villa w/ private pool, great entertainment space, easy walk to beach.

                                Trelawny Parish / Duncans

                                Duncans villa

                                3 8 min stay varies

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

                                Price per night from

                                $292

                                Responds fast!
                                avg. 1 hour 57 minutes

                                Price per night from

                                $292

                                (2) Excellent 

                                  31

                                  Selah - Runaway Bay 4 Bedroom Beachfront

                                  St. Ann Parish / Runaway Bay

                                  Runaway Bay house

                                  4 8 min stay varies

                                  • 4 bedrooms
                                  • sleeps 8
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Ask about children

                                  Price per night from

                                  $1,426

                                  Price per night from

                                  $1,426

                                  (19) Excellent 

                                  Certificate of Excellence

                                    47

                                    Villa Gilgal - Possibilities Are Endless....

                                    Westmoreland Parish / White House

                                    White House villa

                                    4 8 min stay varies

                                    • 4 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Nearest beach 10 mi
                                    • Swimming pool
                                    • Child Friendly

                                    Certificate of Excellence

                                    Price per night from

                                    $801

                                    Responds fast!
                                    avg. 1 hour 5 minutes

                                    Price per night from

                                    $801

                                    (2) Excellent 

                                      34

                                      Seven Seas

                                      Jamaica / St. Ann Parish

                                      Saint Ann Parish villa

                                      4 9 min stay varies

                                      • 4 bedrooms
                                      • sleeps 9
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      “Fantastic!” What a fantastic time we all just had at Seven Seas! Our whole family enjoyed the trip from young to old. Not only was the estate gorgeous, but activities abounded on the property. The snorkeling we were able to enjoy in our own backyard w

                                      Price per night from

                                      $1,000

                                      Price per night from

                                      $1,000

                                        14

                                        Jamaica Luxury near the Beach

                                        St. Andrew Parish / Bull Bay

                                        Bull Bay house

                                        11 34 1 night min

                                        • 11 bedrooms
                                        • sleeps 34
                                        • 1 night min
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $98

                                        Responds fast!
                                        avg. 46 minutes

                                        Price per night from

                                        $98

                                          9

                                          70 steps to the sand

                                          Negril / Negril Beach

                                          Negril Beach condo

                                          2 5 1 night min

                                          • 2 bedrooms
                                          • sleeps 5
                                          • 1 night min
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $171

                                          Responds fast!
                                          avg. 3 hours 58 minutes

                                          Price per night from

                                          $171

                                          (16) Very Good 

                                          Certificate of Excellence

                                            20

                                            Villa @ Richmond Estate with Private Beach

                                            St. Ann Parish / Priory

                                            Priory house

                                            3 7 3 nights min

                                            • 3 bedrooms
                                            • sleeps 7
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 6 mi
                                            • Swimming pool

                                            Certificate of Excellence

                                            Price per night from

                                            $184

                                            Responds fast!
                                            avg. 3 hours 2 minutes

                                            Price per night from

                                            $184

                                            (1) Very Good 

                                              42

                                              Contemporay Central Spacious 2bdrm/2bth/Pool/Toni Comfort Suites

                                              Kingston Parish / Kingston

                                              Kingston apartment

                                              2 4 3 nights min

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

                                              Price per night from

                                              $161

                                              Responds fast!
                                              avg. 2 hours 6 minutes

                                              Price per night from

                                              $161

                                              (4) Excellent 

                                                26

                                                Hummingbird Hill Villa

                                                St. Ann Parish / Runaway Bay

                                                Runaway Bay villa

                                                5 12 3 nights min

                                                • 5 bedrooms
                                                • sleeps 12
                                                • 3 nights min
                                                • Swimming pool
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $571

                                                Price per night from

                                                $571

                                                (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

                                                  (31) Excellent 

                                                    35

                                                    Signature's 21 @ the Country Club

                                                    Kingston Parish / Kingston

                                                    Kingston apartment

                                                    1 3 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 3
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Car not necessary
                                                    “Signature's 21 @ the Country Club was the icing on the cake for my Simply Elegant Wedding Celebration.” The owner and caretaker of Signature's 21 @ the Country Club were both patient, kind and accommodating to our needs from booking to departure. I r

                                                    Price per night from

                                                    $79

                                                    Responds fast!
                                                    avg. 24 minutes

                                                    Price per night from

                                                    $79

                                                    (5) Very Good 

                                                      14

                                                      Shotover Gardens Estate - cottage with pool

                                                      Portland Parish / Port Antonio

                                                      Port Antonio log cabin

                                                      1 2 1 night min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 1 night min
                                                      • Nearest beach 16 mi
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $58

                                                      Price per night from

                                                      $58

                                                        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

                                                          29

                                                          Whispering Waters

                                                          St. Ann Parish / Discovery Bay

                                                          Discovery Bay villa

                                                          7 14 min stay varies

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

                                                          Price per night from

                                                          $2,500

                                                          Price per night from

                                                          $2,500

                                                            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

                                                              Summerhill

                                                              Jamaica / St. James Parish

                                                              Saint James Parish villa

                                                              9 18 min stay varies

                                                              • 9 bedrooms
                                                              • sleeps 18
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $1,671

                                                              Price per night from

                                                              $1,671

                                                              (7) Excellent 

                                                              Certificate of Excellence

                                                                39

                                                                BEAUTIFUL MODERN 1 OR 2 BEDROOM CONDO IN LIGUANEA, KINGSTON, JAMAICA.

                                                                Kingston Parish / Kingston

                                                                Kingston condo

                                                                2 4 min stay varies

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

                                                                Certificate of Excellence

                                                                Price per night from

                                                                $138

                                                                Responds fast!
                                                                avg. 1 hour 49 minutes

                                                                Price per night from

                                                                $138

                                                                (1) Excellent 

                                                                  22

                                                                  Sea Haven

                                                                  St. Ann Parish / Discovery Bay

                                                                  Discovery Bay villa

                                                                  4 8 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  “We fell in love with all of it” This message just to thank you for the wonderfull holiday we had at Sea Haven. Your choice was the absolute perfect one. We have found such a peace in that house that it didn\'t seem real. The whole week was like walkin

                                                                  Price per night from

                                                                  $643

                                                                  Price per night from

                                                                  $643

                                                                  (1) Excellent 

                                                                    15

                                                                    Shotover Gardens Estate - cabin with pool

                                                                    Portland Parish / Port Antonio

                                                                    Port Antonio log cabin

                                                                    1 2 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 1 night min
                                                                    • Nearest beach 16 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $35

                                                                    Price per night from

                                                                    $35

                                                                    (6) Excellent 

                                                                    Certificate of Excellence

                                                                      18

                                                                      Villa BiancaJel, 8 mins from Ocho Rios, a/c, pool, mountain view

                                                                      St. Ann Parish / Ocho Rios

                                                                      Ocho Rios house

                                                                      3 6 2 nights min

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

                                                                      Certificate of Excellence

                                                                      Price per night from

                                                                      $115

                                                                      Responds fast!
                                                                      avg. 51 minutes

                                                                      Price per night from

                                                                      $115

                                                                      (8) Excellent 

                                                                        14

                                                                        Coral Cove Cottage - Linga Awile

                                                                        St. Ann Parish / Discovery Bay

                                                                        Discovery Bay villa

                                                                        3 8 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        “Perfect Vacation” What a fabulous time we all had at Coral Cove! We arrived and were welcomed by the whole staff and made to feel at home right away. The villa was absolutely beautiful. I have stayed at many different villas over the years but the ser

                                                                        Price per night from

                                                                        $429

                                                                        Price per night from

                                                                        $429

                                                                        (5) Very Good 

                                                                          52

                                                                          $80 - $250 per night: Private Villa w/ Ocean Views, Private Pool, Private Beach

                                                                          St. Ann Parish / Ocho Rios

                                                                          Ocho Rios villa

                                                                          3 6 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $286

                                                                          Responds fast!
                                                                          avg. 1 hour 54 minutes

                                                                          Price per night from

                                                                          $286

                                                                          (16) Excellent 

                                                                            19

                                                                            Sol Mar Villa

                                                                            Trelawny Parish / Silver Sands

                                                                            Silver Sands villa

                                                                            3 6 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 2 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $337

                                                                            Responds fast!
                                                                            avg. 1 hour 56 minutes

                                                                            Price per night from

                                                                            $337

                                                                            (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

                                                                              Certificate of Excellence

                                                                              Price per night from

                                                                              $337

                                                                              Responds fast!
                                                                              avg. 31 minutes

                                                                              Price per night from

                                                                              $337