Old Man Bay Rentals

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388 Houses

(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

    (13) Excellent 

      31

      Villa Caymanas by Grand Cayman Villas and Condos

      Grand Cayman / Old Man Bay

      Old Man Bay house

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Swimming pool
      • Child Friendly
      • Air conditioning
      “A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back y
      …see more

      Price per night from

      $813

      Price per night from

      $813

      (44) Excellent 

        12

        Truly Oceanfront luxury in Grand Cayman

        Grand Cayman / Old Man Bay

        Old Man Bay apartment

        3 6 5 nights min

        • 3 bedrooms
        • sleeps 6
        • 5 nights min
        • Beach / lakeside relaxation
        • Swimming pool
        • Child Friendly
        “Beautiful location” Beautiful view of the ocean and great location right on the beach in a quiet area of cayman. Condo has lots of amenities and a nice-sized swimming pool. We had a great time!
        …see more

        Price per night from

        $258

        Responds fast!
        avg. 2 hours 26 minutes

        Price per night from

        $258

        (1) Excellent 

          23

          YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point

          Grand Cayman / Old Man Bay

          Old Man Bay condo

          3 6 4 nights min

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

          Price per night from

          $327

          Responds fast!
          avg. 1 hour 52 minutes

          Price per night from

          $327

            23

            Coral Cottage Pink by Grand Cayman Villas and Condos

            Grand Cayman / Old Man Bay

            Old Man Bay house

            3 6 min stay varies

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

            Price per night from

            $457

            Price per night from

            $457

              24

              Northern Lights No. 5 by Grand Cayman Villas and Condos

              Grand Cayman / Old Man Bay

              Old Man Bay condo

              3 8 min stay varies

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

              Price per night from

              $258

              Price per night from

              $258

              (13) Excellent 

                27

                Cayman Sands by Grand Cayman Villas and Condos

                Grand Cayman / Old Man Bay

                Old Man Bay house

                5 14 min stay varies

                • 5 bedrooms
                • sleeps 14
                • min stay varies
                • Swimming pool
                • Child Friendly
                • Air conditioning
                “A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms h
                …see more

                Price per night from

                $974

                Price per night from

                $974

                  24

                  Coral Cottage Yellow by Grand Cayman Villas and Condos

                  Grand Cayman / Old Man Bay

                  Old Man Bay house

                  3 6 min stay varies

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

                  Price per night from

                  $457

                  Price per night from

                  $457

                  (22) Excellent 

                    26

                    Grand Cayman Northern Lights Beachfront Villa

                    Grand Cayman / Old Man Bay

                    Old Man Bay condo

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Swimming pool
                    • Child Friendly
                    “A piece of heaven in the Carribean” We arrived at Northern Lights after a long, cold, snowy winter to find a place that exceeded our expectations. Many times during the week, we spoke about how happy we were that we chose Northern Lights. The settin
                    …see more

                    Price per night from

                    $250

                    Price per night from

                    $250

                    (1) Average 

                      29

                      Coral Cottages by Grand Cayman Villas and Condos

                      Grand Cayman / Old Man Bay

                      Old Man Bay house

                      6 12 min stay varies

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

                      Price per night from

                      $911

                      Price per night from

                      $911

                      (4) Excellent 

                        24

                        Villa Spirit

                        Grand Cayman / Old Man Bay

                        Old Man Bay house

                        3 6 min stay varies

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

                        Price per night from

                        $415

                        Price per night from

                        $415

                        Great rentals within 20 miles that match your search

                        Distance approx 13.8 km from Old Man Bay

                        (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

                          $378

                          Responds fast!
                          avg. 2 hours 12 minutes

                          Price per night from

                          $378

                          Distance approx 15.62 km from Old Man Bay

                          (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

                            $189

                            Responds fast!
                            avg. 57 minutes

                            Price per night from

                            $189

                            Distance approx 2.24 km from Old Man Bay

                            (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

                              $264

                              Responds fast!
                              avg. 2 hours 41 minutes

                              Price per night from

                              $264

                              Distance approx 13.67 km from Old Man Bay

                              (1) Excellent 

                                36

                                Spectacular Ground Floor Condo on Seven Mile Beach - Laguna del Mar

                                Grand Cayman / Seven Mile Beach

                                Seven Mile Beach condo

                                3 8 min stay varies

                                • 3 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Child Friendly

                                Price per night from

                                $691

                                Responds fast!
                                avg. 50 minutes

                                Price per night from

                                $691

                                Distance approx 13.96 km from Old Man Bay

                                  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

                                  $293

                                  Price per night from

                                  $293

                                  Distance approx 13.72 km from Old Man Bay

                                    34

                                    Seven Mile Beach - Sunset Cove - Garden View

                                    Grand Cayman / Seven Mile Beach

                                    Seven Mile Beach condo

                                    2 4 4 nights min

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

                                    Price per night from

                                    $276

                                    Price per night from

                                    $276

                                    Distance approx 13.66 km from Old Man Bay

                                    (17) Excellent 

                                    Certificate of Excellence

                                      68

                                      Cayman Reef Resort 29 - Ocean Front Resort

                                      Grand Cayman / Seven Mile Beach

                                      Seven Mile Beach apartment

                                      3 7 4 nights min

                                      • 3 bedrooms
                                      • sleeps 7
                                      • 4 nights min
                                      • Beach / lakeside relaxation
                                      • Child Friendly
                                      • Air conditioning
                                      “Location, Location, location!!!!” Location was absolutely perfect. You could walk to most places and although we had a car, we didn't need it while at this condo. The owner was very sensitive to ensuring we had everything we needed and felt comfortabl
                                      …see more

                                      Certificate of Excellence

                                      Price per night from

                                      $1,026

                                      Price per night from

                                      $1,026

                                      Distance approx 6.52 km from Old Man Bay

                                      (5) Excellent 

                                        28

                                        Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-6

                                        Grand Cayman / North Side

                                        North Side condo

                                        2 6 min stay varies

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

                                        Price per night from

                                        $293

                                        Price per night from

                                        $293

                                        Distance approx 14.21 km from Old Man Bay

                                        (17) Excellent 

                                          21

                                          Oceanfront directly on 7 Mile Beach - Email for Specials!

                                          Grand Cayman / Seven Mile Beach

                                          Seven Mile Beach apartment

                                          2 5 min stay varies

                                          • 2 bedrooms
                                          • sleeps 5
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly
                                          “The perfect location...Coffee in the morning on the porch with the ocean.” We just returned from a 10 night stay in Unit 11. This condo complex is away from the crowds of the big hotels but still has the perfect private stretch of 12 mile beach. Jim a
                                          …see more

                                          Price per night from

                                          $435

                                          Price per night from

                                          $435

                                          Distance approx 5.64 km from Old Man Bay

                                          (9) Very Good 

                                            38

                                            The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,

                                            Grand Cayman / East End

                                            East End condo

                                            1 4 7 nights min

                                            • 1 bedroom
                                            • sleeps 4
                                            • 7 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $214

                                            Price per night from

                                            $214

                                            Distance approx 14.06 km from Old Man Bay

                                            (4) Excellent 

                                              18

                                              Beach Is 37 Steps From Front Door!!!

                                              Grand Cayman / West Bay

                                              West Bay condo

                                              1 4 3 nights min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 3 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.1 mi
                                              • Swimming pool

                                              Price per night from

                                              $323

                                              Responds fast!
                                              avg. 3 hours 24 minutes

                                              Price per night from

                                              $323

                                              Distance approx 13.59 km from Old Man Bay

                                              (12) Excellent 

                                              Certificate of Excellence

                                                55

                                                Cayman Reef Resort #50 - Best Value on the Beach

                                                Grand Cayman / Seven Mile Beach

                                                Seven Mile Beach apartment

                                                1 4 3 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 3 nights min
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly
                                                “Excellent Long Term Stay” Unit 50 was very suitable for my wife and me for a four week visit. We thought the overall experience was excellent and it provided excellent value for our money. We would definitely recommend Unit 50 and we plan to retu
                                                …see more

                                                Certificate of Excellence

                                                Price per night from

                                                $528

                                                Price per night from

                                                $528

                                                Distance approx 13.69 km from Old Man Bay

                                                  24

                                                  On the Beach -- As Good As It Gets

                                                  Grand Cayman / George Town

                                                  George Town house

                                                  5 10 7 nights min

                                                  • 5 bedrooms
                                                  • sleeps 10
                                                  • 7 nights min
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Suitable for children age 5+

                                                  Price per night from

                                                  $4,186

                                                  Price per night from

                                                  $4,186

                                                  Distance approx 5.52 km from Old Man Bay

                                                  (1) Excellent 

                                                    32

                                                    Morritt's Tortuga Club: Studio, Sleeps 2, Full Kitchen

                                                    Grand Cayman / East End

                                                    East End condo

                                                    1 2 7 nights min

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

                                                    Price per night from

                                                    $147

                                                    Price per night from

                                                    $147

                                                    Distance approx 14.82 km from Old Man Bay

                                                    (1) Very Good 

                                                      18

                                                      Cayman Island Splendor at the Iron Shore House

                                                      Grand Cayman / West Bay

                                                      West Bay guest house

                                                      3 2 1 night min

                                                      • 3 bedrooms
                                                      • sleeps 2
                                                      • 1 night min
                                                      • Nearest beach 2 mi
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $112

                                                      Responds fast!
                                                      avg. 6 minutes

                                                      Price per night from

                                                      $112

                                                      Distance approx 13.66 km from Old Man Bay

                                                      (18) Excellent 

                                                      Certificate of Excellence

                                                        49

                                                        Cayman Reef Resort #32 - Steps away from the Beach

                                                        Grand Cayman / Seven Mile Beach

                                                        Seven Mile Beach apartment

                                                        1 4 3 nights min

                                                        • 1 bedroom
                                                        • sleeps 4
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Certificate of Excellence

                                                        Price per night from

                                                        $698

                                                        Price per night from

                                                        $698

                                                        Distance approx 13.53 km from Old Man Bay

                                                        (1) Excellent 

                                                          19

                                                          Heart of Seven Mile Beach

                                                          Grand Cayman / Seven Mile Beach

                                                          Seven Mile Beach apartment

                                                          3 6 2 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 2 nights min
                                                          • Nearest beach 0 mi
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $469

                                                          Responds fast!
                                                          avg. 2 hours 4 minutes

                                                          Price per night from

                                                          $469

                                                          Distance approx 14.07 km from Old Man Bay

                                                            25

                                                            Sea Jewel, 2BR, 2BA, oceanview villa

                                                            Grand Cayman / West Bay

                                                            West Bay villa

                                                            2 6 5 nights min

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

                                                            Price per night from

                                                            $381

                                                            Price per night from

                                                            $381

                                                            Distance approx 13.42 km from Old Man Bay

                                                            (32) Excellent 

                                                              46

                                                              Casa Caribe penths oceanvw Condo #18 Heart of 7-Mile Beach near Ritz 15% off Apr

                                                              Grand Cayman / Seven Mile Beach

                                                              Seven Mile Beach apartment

                                                              3 7 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Car not necessary
                                                              “Perfectly perfect!!!” This penthouse was perfect for our 8 day vacation. The unit was beautifully decorated and set up for cooking with all the spices, pans, etc. needed. The beach was a few steps away from our unit, with views from the deck of a pe
                                                              …see more

                                                              Price per night from

                                                              $410

                                                              Price per night from

                                                              $410

                                                              Distance approx 13.67 km from Old Man Bay

                                                              (40) Excellent 

                                                                39

                                                                Magnificent Ocean Views in the Heart of 7 Mile Beach !! Fully Stocked!

                                                                Grand Cayman / Seven Mile Beach

                                                                Seven Mile Beach condo

                                                                2 4 1 night min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 1 night min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning
                                                                “A Peaceful Place In Paradise” Where do I begin ~ My first trip to Grand Cayman Islands and staying at "Regal Beach" in the beautiful, bright, clean, two-bedroom Condo in paradise was truly amazing! The condo not only has a beautiful view of the Car
                                                                …see more

                                                                Price per night from

                                                                $296

                                                                Responds fast!
                                                                avg. 2 hours 54 minutes

                                                                Price per night from

                                                                $296

                                                                Distance approx 14.32 km from Old Man Bay

                                                                (11) Excellent 

                                                                  29

                                                                  Sea Breeze - A Luxury 4br + den SMB Condo

                                                                  Grand Cayman / Seven Mile Beach

                                                                  Seven Mile Beach condo

                                                                  4 10 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 10
                                                                  • 7 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 0.1 mi
                                                                  • Swimming pool

                                                                  Price per night from

                                                                  $922

                                                                  Price per night from

                                                                  $922

                                                                  Distance approx 14.67 km from Old Man Bay

                                                                  (8) Excellent 

                                                                    21

                                                                    GCAYMAN: Your Very Own Private Seven Mile Beach Area Tropical Blue Guest Home

                                                                    Grand Cayman / Seven Mile Beach

                                                                    Seven Mile Beach guest house

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.1 mi
                                                                    • Child Friendly
                                                                    “Cayman Relaxed” What a great place. Away from the congestion of seven mile beach. Two good restaurants, beach and a grocery store within walking distance. We made good use of the two outdoor hammocks. Nicely appointed kitchen although we just used
                                                                    …see more

                                                                    Price per night from

                                                                    $235

                                                                    Price per night from

                                                                    $235

                                                                    Distance approx 5.69 km from Old Man Bay

                                                                      24

                                                                      Grand Cayman: large 2 bedroom,2 bedroom apartment with a sea view terrace

                                                                      Grand Cayman / Bodden Town

                                                                      Bodden Town apartment

                                                                      2 4 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • min stay varies
                                                                      • Nearest beach 0.1 mi
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $76

                                                                      Responds fast!
                                                                      avg. 59 minutes

                                                                      Price per night from

                                                                      $76

                                                                      Distance approx 6.47 km from Old Man Bay

                                                                        37

                                                                        Cos Kai - 5 Bedrooms at Rum Point - Book Now

                                                                        Grand Cayman / Rum Point

                                                                        Rum Point villa

                                                                        5 15 5 nights min

                                                                        • 5 bedrooms
                                                                        • sleeps 15
                                                                        • 5 nights min
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $1,229

                                                                        Price per night from

                                                                        $1,229

                                                                        Distance approx 13.94 km from Old Man Bay

                                                                        (6) Excellent 

                                                                          20

                                                                          Sea Breeze 5 luxury 4 bedroom on SMB

                                                                          Grand Cayman / Seven Mile Beach

                                                                          Seven Mile Beach condo

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Ask about children

                                                                          Price per night from

                                                                          $1,024

                                                                          Price per night from

                                                                          $1,024

                                                                          Distance approx 5.44 km from Old Man Bay

                                                                            14

                                                                            Tequila Sunrise Villa

                                                                            Grand Cayman / East End

                                                                            East End villa

                                                                            3 10 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 10
                                                                            • min stay varies
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $352

                                                                            Responds fast!
                                                                            avg. 2 hours 58 minutes

                                                                            Price per night from

                                                                            $352

                                                                            Distance approx 13.43 km from Old Man Bay

                                                                            (1) Excellent 

                                                                              33

                                                                              Mora - 7 Bedrooms at South Sound - Book Now

                                                                              Grand Cayman / George Town

                                                                              George Town villa

                                                                              7 18 min stay varies

                                                                              • 7 bedrooms
                                                                              • sleeps 18
                                                                              • min stay varies
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $1,945

                                                                              Price per night from

                                                                              $1,945