What our guests had to say...

"We are having a fantastic time. Your house is wonderful and everyone has been amazing! Thank you for checking in on us. We are very happy here =) "

Mindy - New York

"I wanted to write and thank you for your incredible hospitality at Head O’Bay. Your property is lovely, and I definitely will be returning, hopefully sooner than later! I definitely did not want to leave Little Cayman. What an amazing little island. We so enjoyed ourselves, and Head O’ Bay will be highly recommended. Trevor is so welcoming and went out of his way to give us a tour of the island when we first landed. What a memorable experience, thanks to you both."

Visiting Journalist

"Thank you so much for the use of your home! It is fantastic! I tried to find a way to stay! Trevor was wonderful! I asked for a knife to cut open a coconut and (you would be proud) he said no but had Lowell open 2 for me. So many times we have been to the islands and I have not taken the time to enjoy a fresh coconut. Our friends (Tim and Hannah) from the U.K. also had a wonderful time. Tim really wanted fresh fish and Trevor really came through for us. Trevor and Lowell seemed always available but gave us some distance to enjoy the peace and quiet. The diving was great, lot of great pics and video. Would like to be there next time during lobster season. I have your site saved under my favorites. Thank again, the home that you all have built and your love for the island is incredible!"

Karyn and Thomas

"Can't say enough about Little Cayman and Head O'Bay. Definitely the best fishing and diving I have ever experienced!!!!!"

Dayna - Alachua, FL

"Little Cayman diving is some of the best we have ever experienced. Head O'Bay is a beautiful and comfortable home. We'll be back."

Jim - Miami, FL

"We just wanted you to know how happy we are with everything. Your son, Walter, has been most gracious and helpful. Our boys are in pradise. They love the freedom that the little boat affords them and we are enjoying seeing them so occupied. They are out with Lowell as I write and then this afternoon they are off for a dive. as my one son said.."what a classic day!" If they catch a fish it will make it even better. We are off to Point of Sands while they fish. Many thanks for the opportunity to enjoy this wonderful part of the world."



  • Two king size bedrooms with two adjoining bathrooms
  • Central air conditioning
  • Queen studio couch
  • Large full front porch
  • New electrical applicances including dishwasher, refrigerator, washer and dryer
  • Well equipped kitchen
  • Barbeque grill for cooking out
  • TV with satellite service
  • DVD or VCR (bring your own movies or rent one from the Village Square)
  • Daily maid services available
  • No phones but you can rent cell phones from Village Square
  • Annual inspection by the Cayman Islands Department of Tourism to ensure the quality and service you expect on your vacation.