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91 villas

    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

    $1,148

    Price per night from

    $1,148

    (5) Excellent 

      24

      SUMMER/FALL RATES DISCOUNTED!/OCEANFRONT VILLA ON PRIVATE SANDY BEACH!!

      Grand Cayman / Rum Point

      Rum Point villa

      3 6 min stay varies

      • 3 bedrooms
      • sleeps 6
      • min stay varies
      • Beach / lakeside relaxation
      • Child Friendly
      • Air conditioning
      “Absolutely loved this place!” Beach and snorkeling at your doorstep. Love the quiet side of the Island! Clean and comfortable-not overly fancy--perfect for a beach house. Melinda has beach towels and coolers, as well as a few snorkel masks, water s

      Price per night from

      $231

      Responds fast!
      avg. 2 hours 35 minutes

      Price per night from

      $231

      (1) Excellent 

        10

        Beautiful Sea Dreams Villa

        Cayman Islands / Cayman Brac

        Cayman Brac villa

        2 4 4 nights min

        • 2 bedrooms
        • sleeps 4
        • 4 nights min

        Price per night from

        $208

        Price per night from

        $208

        (6) Excellent 

        Certificate of Excellence

          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

          Certificate of Excellence

          Price per night from

          $402

          Responds fast!
          avg. 28 minutes

          Price per night from

          $402

            45

            SUMMER PROMO - 3 Bedroom Plus Den Beach Front Home in West Bay - Sleeps 10!

            Grand Cayman / West Bay

            West Bay villa

            3 10 min stay varies

            • 3 bedrooms
            • sleeps 10
            • min stay varies
            • Ask about children

            Price per night from

            $1,145

            Price per night from

            $1,145

              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

              $317

              Price per night from

              $317

              (13) Excellent 

                12

                Cayman Brac Beach Villas. Beach Front 2-12 people!

                Cayman Islands / Cayman Brac

                Cayman Brac villa

                5 12 4 nights min

                • 5 bedrooms
                • sleeps 12
                • 4 nights min
                • Beach / lakeside relaxation
                • Ask about children
                • Air conditioning
                “Best beach on the island” We just returned from our 2 week stay at Brac Beach Villa. It was amazing. Anytime you can leave the cold winter behind for a tropical destination it is worth it. Our Villa by far had the best beach on the island, the pool wa

                Price per night from

                $173

                Price per night from

                $173

                (21) Excellent 

                Certificate of Excellence

                  18

                  Gorgeous Beachfront Villa, Azure Breeze #5

                  Grand Cayman / North Side

                  North Side villa

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning
                  “Absolutely beautiful home and beach!” Beautiful beach home on the quieter end of the island. Snorkeling right outside your door. Close to Rum point , Starfish beach , and nice restaurants. Would HIGHLY recommend this place if you are looking for a

                  Certificate of Excellence

                  Price per night from

                  $328

                  Price per night from

                  $328

                    24

                    Lovely Stake Bay 'Sea Dreams Villa’ w/Ocean Views!

                    Cayman Islands / Cayman Brac

                    Cayman Brac villa

                    2 4 4 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 4 nights min
                    • Air conditioning

                    Price per night from

                    $161

                    Responds fast!
                    avg. 11 minutes

                    Price per night from

                    $161

                    (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

                      Price per night from

                      $272

                      (7) Excellent 

                        22

                        Morning Glory

                        Grand Cayman / Savannah

                        Savannah villa

                        7 14 min stay varies

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

                        Price per night from

                        $980

                        Price per night from

                        $980

                          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

                          $262

                          Price per night from

                          $262

                            11

                            Queen Room + Bath (Hibiscus Room)

                            Grand Cayman / George Town

                            George Town villa

                            1 2 3 nights min

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

                            Price per night from

                            $156

                            Price per night from

                            $156

                              25

                              Hidden Escape

                              Grand Cayman / Savannah

                              Savannah villa

                              4 10 7 nights min

                              • 4 bedrooms
                              • sleeps 10
                              • 7 nights min
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $297

                              Price per night from

                              $297

                              (1) Excellent 

                                26

                                Gypsy by Grand Cayman Villas and Condos

                                Grand Cayman / Rum Point

                                Rum Point villa

                                4 10 min stay varies

                                • 4 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning
                                “A 50th birthday celebration in paradise!” I wanted a relaxing setting away from the crowds. Gypsy provided us with that and so much more. The home is spacious yet cozy, elegant and relaxed. Floor to ceiling windows on the ocean side of the house takes

                                Price per night from

                                $835

                                Responds fast!
                                avg. 2 hours 37 minutes

                                Price per night from

                                $835

                                (1) Excellent 

                                  23

                                  Mahogany Point 5

                                  Grand Cayman / North Side

                                  North Side villa

                                  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

                                    16

                                    Lime Tree Villa

                                    Grand Cayman / Camana Bay

                                    Camana Bay villa

                                    4 10 min stay varies

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

                                    Price per night from

                                    $598

                                    Price per night from

                                    $598

                                    (3) Excellent 

                                      38

                                      SUMMER PROMO - 4-Bedroom Secluded Balinese Custom Home with Private Theatre

                                      Grand Cayman / East End

                                      East End villa

                                      4 10 min stay varies

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

                                      Price per night from

                                      $1,728

                                      Price per night from

                                      $1,728

                                      (4) Excellent 

                                        38

                                        SUMMER PROMO - 4-Story, 6-Bedroom, Modern 12,000 sqft Beachfront Mega-Mansion

                                        Grand Cayman / East End

                                        East End villa

                                        6 23 min stay varies

                                        • 6 bedrooms
                                        • sleeps 23
                                        • min stay varies
                                        • Swimming pool
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $2,150

                                        Price per night from

                                        $2,150

                                        (15) Excellent 

                                          36

                                          25% OFF - 6 Bedroom Dramatic Oceanfront Estate with Private Beach

                                          Grand Cayman / Breakers

                                          Breakers villa

                                          6 16 min stay varies

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

                                          Price per night from

                                          $2,150

                                          Price per night from

                                          $2,150

                                          (2) Excellent 

                                            14

                                            Addison & Lee Cayman Villa

                                            Grand Cayman / George Town

                                            George Town villa

                                            6 14 3 nights min

                                            • 6 bedrooms
                                            • sleeps 14
                                            • 3 nights min
                                            • Child Friendly

                                            Price per night from

                                            $1,140

                                            Price per night from

                                            $1,140

                                            (1) Very Good 

                                              38

                                              Grand Cayman Islands Ocean front Villa with 2 bedrooms and 2 baths

                                              Grand Cayman / West Bay

                                              West Bay villa

                                              2 6 3 nights min

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

                                              Price per night from

                                              $443

                                              Responds fast!
                                              avg. 2 hours 48 minutes

                                              Price per night from

                                              $443

                                              (8) Excellent 

                                                45

                                                SUMMER PROMO - 6-Bedroom Beachfront with 150' Pool, 2 Hot Tubs and 2 Fire Pit

                                                Grand Cayman / George Town

                                                George Town villa

                                                6 16 min stay varies

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

                                                Price per night from

                                                $2,874

                                                Price per night from

                                                $2,874

                                                  21

                                                  Luxurious, 7-Bedroom, Balinese-Inspired Beachfront Home

                                                  Grand Cayman / Rum Point

                                                  Rum Point villa

                                                  7 16 min stay varies

                                                  • 7 bedrooms
                                                  • sleeps 16
                                                  • min stay varies
                                                  • Ask about children

                                                  Price per night from

                                                  $2,874

                                                  Price per night from

                                                  $2,874

                                                  (29) Excellent 

                                                    38

                                                    SUMMER PROMO - 4-Bedroom Private, Modern Family Bungalow on Seven Mile Beach

                                                    Grand Cayman / West Bay

                                                    West Bay villa

                                                    5 12 min stay varies

                                                    • 5 bedrooms
                                                    • sleeps 12
                                                    • min stay varies
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning
                                                    “Private & Well Maintained” This is the second time we've rented Serenity Now, so that speaks for itself. We travel with another family, so there are four children under age eight between us. The house is extremely kid-friendly, especially the pool,

                                                    Price per night from

                                                    $1,145

                                                    Price per night from

                                                    $1,145

                                                    (1) Excellent 

                                                      19

                                                      Flip Flop Kai

                                                      Grand Cayman / North Side

                                                      North Side villa

                                                      3 8 min stay varies

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

                                                      Price per night from

                                                      $453

                                                      Price per night from

                                                      $453

                                                      (2) Excellent 

                                                        22

                                                        Coco Kai Beach Front Villa -Cayman Kai

                                                        Grand Cayman / North Side

                                                        North Side villa

                                                        6 15 1 night min

                                                        • 6 bedrooms
                                                        • sleeps 15
                                                        • 1 night min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $863

                                                        Responds fast!
                                                        avg. 14 minutes

                                                        Price per night from

                                                        $863

                                                        (11) Very Good 

                                                          31

                                                          Caribbean Paradise 9

                                                          Grand Cayman / George Town

                                                          George Town villa

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning
                                                          “Wonderful vacation with a view” The house was clean, well stocked and in a very quiet (relaxing) area. Close to downtown Georgetown and the airport if you rent a car which I highly recommend. The best part was the view and private beach area. We had

                                                          Price per night from

                                                          $357

                                                          Price per night from

                                                          $357

                                                            30

                                                            Present Moment

                                                            Grand Cayman / Bodden Town

                                                            Bodden Town villa

                                                            4 12 min stay varies

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

                                                            Price per night from

                                                            $654

                                                            Price per night from

                                                            $654

                                                            (11) Excellent 

                                                              27

                                                              Ocean Oasis

                                                              Grand Cayman / North Side

                                                              North Side villa

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning
                                                              “GREAT PLACE” Really a great place for a family vacation. The pool was perfect for adults and our grandson age 21 mo. was perfect with the ledge area, so he could get in and play. The attractions were visited and very nice. Games , books and info of

                                                              Price per night from

                                                              $498

                                                              Price per night from

                                                              $498

                                                              (3) Very Good 

                                                                28

                                                                Serenity Sands

                                                                Grand Cayman / Bodden Town

                                                                Bodden Town villa

                                                                2 4 min stay varies

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

                                                                Price per night from

                                                                $252

                                                                Price per night from

                                                                $252

                                                                  30

                                                                  Kai Zen by Grand Cayman Villas and Condos

                                                                  Grand Cayman / Rum Point

                                                                  Rum Point villa

                                                                  3 6 min stay varies

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

                                                                  Price per night from

                                                                  $662

                                                                  Responds fast!
                                                                  avg. 2 hours 37 minutes

                                                                  Price per night from

                                                                  $662

                                                                  (3) Very Good 

                                                                    16

                                                                    Sea Magic

                                                                    Grand Cayman / North Side

                                                                    North Side villa

                                                                    2 7 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 7
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    “Rum Point ... Sea Magic” Wonderful newly remodeled home with lots of amenities not the least of which is the huge hot tub. The house is located in a very quiet area of Rum Point yet very close to the Rum Point beach club. Would highly recommend and

                                                                    Price per night from

                                                                    $297

                                                                    Price per night from

                                                                    $297

                                                                    (4) Excellent 

                                                                      50

                                                                      SPRING PROMO - Ultra-Cool 6-Bedroom Beachfront Mansion in Rum Point

                                                                      Grand Cayman / Rum Point

                                                                      Rum Point villa

                                                                      5 18 min stay varies

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

                                                                      Price per night from

                                                                      $2,512

                                                                      Price per night from

                                                                      $2,512

                                                                        26

                                                                        Hilltime by Grand Cayman Villas and Condos

                                                                        Grand Cayman / Rum Point

                                                                        Rum Point villa

                                                                        4 8 min stay varies

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

                                                                        Price per night from

                                                                        $685

                                                                        Responds fast!
                                                                        avg. 2 hours 37 minutes

                                                                        Price per night from

                                                                        $685

                                                                        (10) Very Good 

                                                                          24

                                                                          Coral Reef

                                                                          Grand Cayman / Seven Mile Beach

                                                                          Seven Mile Beach villa

                                                                          7 25 min stay varies

                                                                          • 7 bedrooms
                                                                          • sleeps 25
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          “This beautiful home has everything you need!” We had a blast staying at Coral Reef. There were 6 adults and 2 kids (ages 9 & 13). There was plenty of room for hanging out, eating breakfast, playing games, swimming and playing on the beach. We never

                                                                          Price per night from

                                                                          $2,875

                                                                          Price per night from

                                                                          $2,875

                                                                            27

                                                                            SUMMER PROMO - 3-Bedroom Luxury Villa on a Spectacular Cove Beach

                                                                            Grand Cayman / George Town

                                                                            George Town villa

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Ask about children

                                                                            Price per night from

                                                                            $1,045

                                                                            Price per night from

                                                                            $1,045

                                                                            (14) Excellent 

                                                                              25

                                                                              SUMMER PROMO - 4-Bedroom, Breezy, Ocean Estate with Rolling Surf Views

                                                                              Grand Cayman / Bodden Town

                                                                              Bodden Town villa

                                                                              4 10 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              “Amazing Vacation!!!” Very impressive house and property right on the ocean. We were 3 couples and 2 kids and the floor plan was absolutely perfect for us. Each room has it's own bathroom. We cooked most meals in the chef's kitchen and ate family st

                                                                              Price per night from

                                                                              $1,145

                                                                              Price per night from

                                                                              $1,145