Vacation Rentals with Pool in Cayman Islands

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Filtering by: Swimming pool

283 vacation rentals

(27) Excellent 

    48

    Beachfront Cayman Island Condo on 7 mile beach

    Grand Cayman / Seven Mile Beach

    Seven Mile Beach apartment

    3 7 min stay varies

    • 3 bedrooms
    • sleeps 7
    • min stay varies
    • Beach / lakeside relaxation
    • Swimming pool
    • Child Friendly
    “A DREAM COME TRUE” We are the type of people who always look for affordable alternatives to the fancy hotels and the condo we rented from Anandi was just what we needed. Comfortably spacious and well stocked, No 329 Sunset Cove became our home from
    …see more

    Price per night from

    $422

    Price per night from

    $422

    (16) Excellent 

      59

      SMB-Grand 32, renovated 2Bd/2Bath,

      Grand Cayman / Seven Mile Beach

      Seven Mile Beach apartment

      2 6 min stay varies

      • 2 bedrooms
      • sleeps 6
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 0.1 mi
      • Swimming pool

      Price per night from

      $176

      Responds fast!
      avg. 1 hour 22 minutes

      Price per night from

      $176

      (36) Excellent 

      Certificate of Excellence

        27

        2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.2

        Grand Cayman / Rum Point

        Rum Point apartment

        2 4 min stay varies

        • 2 bedrooms
        • sleeps 4
        • min stay varies
        • Beach / lakeside relaxation
        • Nearest beach 0 mi
        • Swimming pool
        “Perfect in every way!” Hubby and I just returned from our 2 week stay in the Moonlight Kai condo. We had no concerns at all after reading all the wonderful reviews. The condo is and has almost everything listed (I'll explain further in my review) and
        …see more

        Certificate of Excellence

        Price per night from

        $207

        Price per night from

        $207

        (1) Excellent 

          41

          Coconut Beach by Grand Cayman Villas and Condos

          Grand Cayman / Rum Point

          Rum Point house

          5 12 min stay varies

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

          Price per night from

          $1,140

          Price per night from

          $1,140

          (5) Excellent 

            16

            “Everything about this place is first class!”

            Cayman Islands / Cayman Brac

            Cayman Brac villa

            3 8 min stay varies

            • 3 bedrooms
            • sleeps 8
            • min stay varies
            • Nearest beach 0 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $400

            Responds fast!
            avg. 31 minutes

            Price per night from

            $400

            (13) Excellent 

              32

              Three Little Birds -2BR+ Villa, Private Beach

              Grand Cayman / Rum Point

              Rum Point house

              2 6 4 nights min

              • 2 bedrooms
              • sleeps 6
              • 4 nights min
              • Beach / lakeside relaxation
              • Swimming pool
              • Child Friendly
              “Gorgeous, peaceful- perfect island setting!” We rarely saw any other guests while staying at Three Little Birds. The place is well appointed, clean, comfortable, with a fully stocked kitchen; lovely sitting room overlooking the little beach. Swimming
              …see more

              Price per night from

              $573

              Price per night from

              $573

              (15) Excellent 

                20

                Laguna del Mar: Prime Seven Mile Beach location ground floor beachfront

                Grand Cayman / Seven Mile Beach

                Seven Mile Beach condo

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Nearest beach 0 mi
                • Swimming pool
                • Child Friendly

                Price per night from

                $675

                Responds fast!
                avg. 50 minutes

                Price per night from

                $675

                (38) Excellent 

                  43

                  3 Bed Condo with Huge Patio on Seven Mile Beach

                  Grand Cayman / Seven Mile Beach

                  Seven Mile Beach apartment

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 0 mi
                  • Swimming pool
                  “Excellent Condo With Very Attentive Owner” This is an excellent condo with wonderful view and large terrace. Its spacious and well worth the climb of three stairs. The apartment was probably the best equipped rental we have EVER stayed in (and we have
                  …see more

                  Price per night from

                  $371

                  Responds fast!
                  avg. 2 hours 12 minutes

                  Price per night from

                  $371

                  (28) Excellent 

                    21

                    "A Mid-Winter Night's Dream" Grand Cayman Oceanfront, Quiet, Secluded, Rum Point

                    Grand Cayman / North Side

                    North Side apartment

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Swimming pool
                    • Child Friendly
                    “Loved it” We loved the Rum Point area. The condo was clean. Pool area was clean. We enjoyed the area enough for us to do. When we wanted to do more drove 45 minutes to Seven Mile Beach. Just a great location
                    …see more

                    Price per night from

                    $258

                    Responds fast!
                    avg. 2 hours 41 minutes

                    Price per night from

                    $258

                      48

                      Amazing beach villa, with free electric car to explore the island

                      Grand Cayman / West Bay

                      West Bay villa

                      4 8 7 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 7 nights min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $1,149

                      Price per night from

                      $1,149

                      (5) Very Good 

                        27

                        Two Rainbows by Grand Cayman Villas and Condos

                        Grand Cayman / Rum Point

                        Rum Point house

                        5 10 min stay varies

                        • 5 bedrooms
                        • sleeps 10
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning
                        “Two Rainbows is a peaceful, secluded and affordable villa perfec” Our stay at Two Rainbows was our fourth visit to Grand Cayman. Check-in was absolutely painless. We had great instructions and were able to walk right in a get settled in a matter of
                        …see more

                        Price per night from

                        $1,260

                        Price per night from

                        $1,260

                        (11) Excellent 

                          13

                          Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6

                          Grand Cayman / North Side

                          North Side apartment

                          2 6 3 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Swimming pool
                          • Child Friendly
                          “Perfect paradise” This was perfect for my family of 2 teenage girls, my wife and I. We wanted the hot Caribbean vacation without the resort. We dove and explored everyday. This condo had everything we needed, pool, right on the sea, internet, full kit
                          …see more

                          Price per night from

                          $288

                          Responds fast!
                          avg. 3 hours 49 minutes

                          Price per night from

                          $288

                          (9) Excellent 

                          Certificate of Excellence

                            39

                            Ocean Views Long Sunsets 25 steps to water Ground Floor, pool outside front door

                            Grand Cayman / Seven Mile Beach

                            Seven Mile Beach apartment

                            2 4 min stay varies

                            • 2 bedrooms
                            • sleeps 4
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Swimming pool
                            • Child Friendly

                            Certificate of Excellence

                            Price per night from

                            $328

                            Responds fast!
                            avg. 42 minutes

                            Price per night from

                            $328

                            (30) Excellent 

                              48

                              Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt

                              Grand Cayman / North Side

                              North Side apartment

                              2 6 min stay varies

                              • 2 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 0.15 mi
                              • Swimming pool
                              “Tranquility” Traveled to Grand Cayman with a couple girlfriends and chose Kai Kotch based on reviews here and was not disappointed! We wanted a peaceful vacation and that's exactly what we got. Kai Kotch #17 was spacious and clean and we really enjoye
                              …see more

                              Price per night from

                              $276

                              Price per night from

                              $276

                              (4) Excellent 

                              Certificate of Excellence

                                19

                                2 BR condo on Seven Mile Beach with ocean views

                                Grand Cayman / Seven Mile Beach

                                Seven Mile Beach condo

                                2 6 min stay varies

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

                                Certificate of Excellence

                                Price per night from

                                $315

                                Responds fast!
                                avg. 3 hours 59 minutes

                                Price per night from

                                $315

                                (2) Excellent 

                                  27

                                  Ocean Pearl Beachfront Townhome Vacation Rental

                                  Grand Cayman / North Side

                                  North Side house

                                  2 6 min stay varies

                                  • 2 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.1 mi
                                  • Swimming pool

                                  Price per night from

                                  $288

                                  Responds fast!
                                  avg. 3 hours 49 minutes

                                  Price per night from

                                  $288

                                  (14) Excellent 

                                    17

                                    Cayman Beachfront at 22 Villas Pappagallo

                                    Grand Cayman / West Bay

                                    West Bay apartment

                                    1 3 min stay varies

                                    • 1 bedroom
                                    • sleeps 3
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0 mi
                                    • Swimming pool

                                    Price per night from

                                    $247

                                    Price per night from

                                    $247

                                    (13) Excellent 

                                      42

                                      'Sun Cloud' Oceanfront Villa in Rum Point!

                                      Grand Cayman / Rum Point

                                      Rum Point house

                                      5 10 min stay varies

                                      • 5 bedrooms
                                      • sleeps 10
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning
                                      “Perfect Sunrises & Sunsets” Our second trip to the island, however this property made it a remarkable stay. A perfect location, tranquil, close to a small store, 4 minutes drive to Rum point and Cayman Kai. The house is beautiful, a view from every
                                      …see more

                                      Price per night from

                                      $831

                                      Responds fast!
                                      avg. 58 minutes

                                      Price per night from

                                      $831

                                        26

                                        Fishbones by Grand Cayman Villas and Condos

                                        Grand Cayman / Gun Bay

                                        Gun Bay house

                                        3 6 min stay varies

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

                                        Price per night from

                                        $687

                                        Price per night from

                                        $687

                                        (3) Excellent 

                                          15

                                          Oceanview/Poolside Condo on Seven Mile Beach

                                          Grand Cayman / George Town

                                          George Town condo

                                          2 6 min stay varies

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

                                          Price per night from

                                          $229

                                          Responds fast!
                                          avg. 16 minutes

                                          Price per night from

                                          $229

                                          (4) Very Good 

                                            29

                                            Cayman Islands Divers Paradise 1st Floor Oceanfront Condo

                                            Grand Cayman / Seven Mile Beach

                                            Seven Mile Beach condo

                                            2 8 3 nights min

                                            • 2 bedrooms
                                            • sleeps 8
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 1 mi
                                            • Swimming pool

                                            Price per night from

                                            $185

                                            Responds fast!
                                            avg. 57 minutes

                                            Price per night from

                                            $185

                                              27

                                              Sea-Esta Beach Front Kaibo Condo

                                              Grand Cayman / Rum Point

                                              Rum Point apartment

                                              2 4 min stay varies

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

                                              Price per night from

                                              $207

                                              Price per night from

                                              $207

                                              (15) Excellent 

                                                24

                                                CoCoCondo - Your Home Away from Home in the Caribbean

                                                Grand Cayman / West Bay

                                                West Bay apartment

                                                3 6 min stay varies

                                                • 3 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 3 mi
                                                • Swimming pool
                                                “Great Place To Stay” The condo has everything we need. We are a family of six with two grown children and smaller children as well. This condo is nicely decorated and clean. The pool is just outside the patio which is so convenient especially with sm
                                                …see more

                                                Price per night from

                                                $316

                                                Responds fast!
                                                avg. 1 hour 14 minutes

                                                Price per night from

                                                $316

                                                (25) Excellent 

                                                Certificate of Excellence

                                                  37

                                                  Starboard Kai Beachfront Home Rum Point Cayman Kai

                                                  Grand Cayman / Rum Point

                                                  Rum Point house

                                                  2 6 5 nights min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 5 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0 mi
                                                  • Swimming pool
                                                  “Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the
                                                  …see more

                                                  Certificate of Excellence

                                                  Price per night from

                                                  $368

                                                  Responds fast!
                                                  avg. 3 hours 29 minutes

                                                  Price per night from

                                                  $368

                                                  (2) Excellent 

                                                    22

                                                    Turtle Crossing, a place to spread out and relax

                                                    Cayman Brac / West End

                                                    West End villa

                                                    3 6 4 nights min

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

                                                    Price per night from

                                                    $272

                                                    Responds fast!
                                                    avg. 2 hours 59 minutes

                                                    Price per night from

                                                    $272

                                                    (6) Very Good 

                                                      24

                                                      Coral Kai by Grand Cayman Villas and Condos

                                                      Grand Cayman / Rum Point

                                                      Rum Point house

                                                      5 10 min stay varies

                                                      • 5 bedrooms
                                                      • sleeps 10
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning
                                                      “Wonderful Spring Break for 2 families” Outside deck was perfect place to relax, great lounge furniture, plenty of space, perfect size pool for kids, large beach area, sea weed visible but not an issue its the ocean there's always going to be some, but
                                                      …see more

                                                      Price per night from

                                                      $1,260

                                                      Price per night from

                                                      $1,260

                                                      (25) Very Good 

                                                        23

                                                        Christmas Palms by Grand Cayman Villas and Condos

                                                        Grand Cayman / Old Man Bay

                                                        Old Man Bay house

                                                        4 10 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning
                                                        “Wedding Week Stay” In a rare occurrence these days, Christmas Palms actually exists as it is portrayed in both photos and video. Everything aspect of our rental was as we hoped for and expected and would have no reservation in staying there again. T
                                                        …see more

                                                        Price per night from

                                                        $802

                                                        Price per night from

                                                        $802

                                                        (14) Excellent 

                                                          24

                                                          Heritage House by Grand Cayman Villas and Condos

                                                          Grand Cayman / Rum Point

                                                          Rum Point house

                                                          4 10 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning
                                                          “Wow! What a great time” We had the pleasure of staying at the Heritage House for a week at the end of april/beginning of May. The house is not centrally located to the the main part of the island, it is beautifully secluded on the North End of the is
                                                          …see more

                                                          Price per night from

                                                          $813

                                                          Price per night from

                                                          $813

                                                            27

                                                            Beach or Pool

                                                            Grand Cayman / East End

                                                            East End villa

                                                            3 8 4 nights min

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

                                                            Price per night from

                                                            $368

                                                            Responds fast!
                                                            avg. 2 hours 15 minutes

                                                            Price per night from

                                                            $368

                                                            (39) Excellent 

                                                              29

                                                              Cayman Sunset, Coconut Bay Oceanfront 3BR near SMB

                                                              Grand Cayman / West Bay

                                                              West Bay apartment

                                                              3 7 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly
                                                              “A wonderful place to stay” We had three generations staying in Cayman Sunset including grandparents and two teenagers for 8 days, It was a great location, with wonderful snorkeling just steps from the patio. Duncan next door was most helpful, and we h
                                                              …see more

                                                              Price per night from

                                                              $344

                                                              Price per night from

                                                              $344

                                                                25

                                                                Palm Heights Residents #5

                                                                Grand Cayman / Camana Bay

                                                                Camana Bay villa

                                                                3 6 min stay varies

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

                                                                Price per night from

                                                                $260

                                                                Price per night from

                                                                $260

                                                                  28

                                                                  Coconut Bay #109

                                                                  Grand Cayman / West Bay

                                                                  West Bay apartment

                                                                  3 6 min stay varies

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

                                                                  Price per night from

                                                                  $260

                                                                  Price per night from

                                                                  $260

                                                                  (5) Very Good 

                                                                    30

                                                                    Great Location & Value! 7mile Beach Condo next to *NEW* Margaritaville Resort

                                                                    Grand Cayman / Seven Mile Beach

                                                                    Seven Mile Beach apartment

                                                                    2 7 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 7
                                                                    • min stay varies
                                                                    • Nearest beach 0.01 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $263

                                                                    Responds fast!
                                                                    avg. 2 hours 43 minutes

                                                                    Price per night from

                                                                    $263

                                                                      9

                                                                      Hilton Estates, Grand Cayman

                                                                      Grand Cayman / George Town

                                                                      George Town house

                                                                      3 6 min stay varies

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

                                                                      Price per night from

                                                                      $287

                                                                      Price per night from

                                                                      $287

                                                                        30

                                                                        'R' Retreat - Canal Front

                                                                        Grand Cayman / Savannah

                                                                        Savannah guest house

                                                                        3 7 3 nights min

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

                                                                        Price per night from

                                                                        $345

                                                                        Price per night from

                                                                        $345

                                                                        (4) Excellent 

                                                                          24

                                                                          Just For Fun by Grand Cayman Villas and Condos

                                                                          Grand Cayman / Rum Point

                                                                          Rum Point house

                                                                          3 6 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          “Great Cayman Experience!!” We just finished our 1-week vacation at Just For Fun. The cute cottage certainly lived up to our expectations. Our family cooks three meals a day at home. The kitchen and new grilling area work perfectly. The kitchen has lot
                                                                          …see more

                                                                          Price per night from

                                                                          $630

                                                                          Price per night from

                                                                          $630

                                                                          (3) Excellent 

                                                                            37

                                                                            Kai Time Island House, Cayman Kai/Rum Point

                                                                            Grand Cayman / Rum Point

                                                                            Rum Point house

                                                                            2 6 min stay varies

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

                                                                            Price per night from

                                                                            $362

                                                                            Responds fast!
                                                                            avg. 2 hours 53 minutes

                                                                            Price per night from

                                                                            $362

                                                                            (2) Excellent 

                                                                              52

                                                                              Surfers Paradise Oceanfront on the "New Seven Mile Beach"...come and relax !

                                                                              Grand Cayman / George Town

                                                                              George Town guest house

                                                                              5 10 2 nights min

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • 2 nights min
                                                                              • Nearest beach 0.01 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $1,145

                                                                              Price per night from

                                                                              $1,145