Your little slice of paradise awaits…

About Us…

Family owned since 1965, Head O’ Bay is located in the heart of Little Cayman, the smallest island of the three Cayman Islands.

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  • – John L

    Head-o-Bay is in the most perfect location in the Cayman Islands. Breezes stroke you from the many vantage points: a hammock between palms, the second floor deck, the gazebo at the end of the jetty. If you’re too hot, walk across the sand and dunk yourself straight into the sea. And the choices to eat are great on Little Cayman (especially the super convenient and best food just next door at SCC). It is paradise, there’s no mistaking that. Inside the beds are really comfy and there’s everything you need.

  • – Milo F

    If I could live there, I would. And believe me, I’ve asked.

  • -Madeleine S

    We stayed for 3 nights - 4 year old, grandparents and couple - and had the most wonderful time! We loved the beautiful views and sitting out on the terrace to soak them up at all hours of the day. We kayaked to Owen’s Island, cycled around and visited point of sand. It was a lovely space to unwind, recharge and have fun! Thank you to Dera for being such a wonderful host.

  • -Shari B

    We had a lovely time at this well appointed property right on the beach on this small, very quiet island. The property caretaker was very helpful and accommodating and we cannot say enough about how much we enjoyed our stay.