Villa, 2 Bedrooms + Convertible bed(s), 3 Baths (Sleeps 6)
Our family has enjoyed vacationing to this spectacular property since 1962, and we're happy to share our little piece of paradise with anyone who wishes to visit.
Owner purchased this Villa in 2006
Why Owner chose Little Cayman
We built our vacation villa to share the Little Cayman experience with others.
What makes this Villa unique
Head O' Bay enjoys a nice breeze most of the year and is conveniently located right on the tip of the sound. This makes access to the bay so easy and Owen's Island is a quick swim from our dock. The bay is a wonderful place to swim, sail, kayak and snorkel. Owen's Island is a tiny little island in the middle of the sound and has one of the best beaches on the whole island. Sunsets there are magnificent!
Pool / Spa
Children allowed - Head O' Bay is very kid friendly!Head O' Bay is very kid friendly!
No smoking - If you must smoke, please smoke outside.If you must smoke, please smoke outside.
Max guests: 6
100% refund if canceled at least 30 days before arrival date. 50% refund if canceled at least 14 days before arrival date.
Damage and incidentals
You will be responsible for any damage to the rental property caused by you or your party during your stay.
The Property is the best location on the Island, No need for Cooling the Trade Winds from the East take care of that. Along with the unobstructed Sunrise every morning. This place is truly a Nature Perserve. I discover something new every time we come to Head O Bay. Tom & Debbie Chew
I am so glad y'all had a wonderful trip, looking forward to hosting you and your family again!
Beautiful views and location
We stayed short four days at the Head O' Bay villa considering what a great location it is at. Right across, short kayaking away is Owen Island with sand beaches and clear, turquoise water for swimming and snorkeling. The house itself is spacious, clean , with beautiful views, comfortable beds and linens, well equipped kitchen and most importantly, friendly, helpful and always available on site manager Trevor. We had a great time and are highly recommending this villa!
We are delighted that y'all had a good stay! thank you so much for choosing Head O' Bay, you're recommendation is very much appreciated!
How do we put into words the incredible vacation we just experienced?
We’ll try, but Head O’Bay and Little Cayman truly have to be experienced to be fully appreciated.
We are so thankful that the wonderful owners of this amazing property called Head O’Bay make it available for regular folks like us to enjoy! It is a unique tropical paradise that is as active or as laid back as you want it to be.
We chose to fill our days with a balance of adventures and relaxation: scuba diving the famous Bloody Bay Wall including a night dive and a wreck dive with LC Reef Divers, paddle boarding to deserted Owen Island for dramatic sunsets, kayaking and Hobie Cat sailing in the bay, bicycling everywhere including the impressive NewYear’s fireworks show at the LC Beach Resort.
The sunrises at Head O’Bay are a profound experience: nothing short of spectacular!
Aside from the beauty of Head O’Bay and Little Cayman, what made the trip so memorable were the wonderful people we had the pleasure of meeting.
First, the owner family and the caretaker of the Head O’Bay were so wonderful and helpful, and they tailored our vacation to be just what we were hoping it would be. Thank you! We enjoyed meeting you!
And the islanders and local residents were so friendly and genuinely nice! We thoroughly enjoyed everyone that we met.
Here’s a tip: anyone visiting Little Cayman needs to allow time to include a visit to the Little Cayman Museum. Tanya, the museum guide is also a scientist and an expert in the ongoing preservation and restoration of the endangered iguanas. Her enthusiasm is contagious!
We also gained an appreciation and respect for the foresight, commitment and generosity that the Tibbetts family has shared with Little Cayman over 3 generations now. It’s a beautiful story that continues today!
Yes, we look forward to returning!
Head Of Bay and Little Cayman are everything claimed, and more!
Enjoy! ...We certainly did!😊�
Rick & Colleen
Wow! y'all had the kind of vacation experience we hope for all of our guests, thank y'all so much for sharing! We hope you come back soon, Happy New Year!!
Nice and quiet getaway
Relaxing trip to Little Cayman. The property is clean and well taken care of. Be sure to bring a streaming device if you want to watch television. The staff is very accommodating.
We are so very happy to be able to provide a peaceful place for vacationers to unwind and relax.
Decompress on Little
We’ve had a great time at Head O’Bay. Trevor was at the house to meet us as we got a lift from the CCMI guys but just as easily he would have picked us up.
It’s all here and the location (facing almost due East) is perfect for sea breeze almost all year.
Leave the windows open and turn off the AC.
Great grill and the bikes were great too.
We live on Grand so always bring meat to grill plus some small bits and pieces from home. But it’s great to see local eggs in the store plus some local bread too.
If I were to have a singular comment/criticism it would be that if one bedroom could have two queens/singles then you could work it for two couples or a family of four like us.
As it was the kids managed it so not a great drama!!
WiFi speed is actually very solid (around 5-8mbps) when you consider where we are. So if you do need to work then that’s easy. Better than rural broadband in the U.K.!!!!
We will definitely be back. At least one more time this year.
thank you so much for the positive review! It was our pleasure to have you stay at Head O' Bay and you and your family are welcome back anytime. We will certainly consider your suggestion on two queens, that is a fantastic idea. I'm very pleased to hear that the internet was working well for y'all.