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Get Away from it All with a Relaxing Cayman Islands Vacation!

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View of the bay from the Villa.
Our private Villa is ready for you to enjoy!
The Villa's deck has a great breeze to enjoy while relaxing.
Our fully-equipped kitchen makes cooking fun while looking out at the bay.
Our two master bedrooms each have its own full bathroom.

Reviews

9.8 out of 10
Exceptional
2 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Pet-friendly
  • Pool
  • Kitchen

Explore the area

Map
Little Cayman, Cayman Islands
  • Little Cayman Beach
  • Owen Island Beach
  • South Hold Sound
  • Little Cayman (LYB-Edward Bodden Airfield)

Rooms & beds

2 bedrooms (sleeps 6)

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining Area

About this property

Get Away from it All with a Relaxing Cayman Islands Vacation!

Head O' Bay is the perfect Caribbean vacation destination for families or couples who want a relaxing and fun-filled island adventure. Located on private property, you are free to relax on the deck or in one of the hammocks and enjoy the breathtaking view of the beautiful, crystal clear Caribbean sea. Owen Island, otherwise known as "The Key", is just a short swim or kayak ride across the bay--it also makes for a great chance to snorkel and see a variety of tropical fish. Tourists from all of the world come to Little Cayman to scuba dive and experience the breathtaking view of The Wall on the north side of the island. Sea turtles, Grouper, and Angelfish are just a few of the tropical life you will see here at Little Cayman. Let us know if you are interested in scuba diving and we will be glad to help you get set up for a diving trip with one of the resorts on the island. Bird-watching is also a favorite pastime of visitors who visit Little Cayman.
The villa is equipped with a full kitchen, washer and dryer, and 2 bedrooms and 3 full baths (2 upstairs and 1 downstairs.) Extra sleeping on the fold out couch is available as well. With a grocery store on Little Cayman meals are easy to prepare.
Come visit our piece of paradise and experience one of the most beautiful places in the world.

Property manager

Owner

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 2:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Head O' Bay is very kid friendly!
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Events

No events allowed
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Pets

Pets allowed: limit 1 total
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Smoking

Smoking is not permitted
If you must smoke, please smoke outside.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Blossom Village

Located in Little Cayman, this villa is on the beach. Three Fathom Wall and Marilyn's Cut (Dive Site) are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Booby Pond Nature Reserve and South Hold Sound. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Little Cayman, Cayman Islands

Restaurants

  • Beach Nuts Bar
  • Hungry Iguana
  • Seahorse Boutique & Coffee Shop
  • Bird Of Paradise
  • Southern Cross Tiki Bar

Frequently asked questions

Is Get Away from it All with a Relaxing Cayman Islands Vacation! pet-friendly?

Yes, this property allows pets (limit 1 total).

What time is check-in at Get Away from it All with a Relaxing Cayman Islands Vacation!?

Check-in begins at 2:00 PM.

What time is check-out at Get Away from it All with a Relaxing Cayman Islands Vacation!?

Checkout is at 11:00 AM.

Where is Get Away from it All with a Relaxing Cayman Islands Vacation! located?

This Little Cayman villa is located by the ocean, nestled on the beach a short distance away from Booby Pond Nature Reserve, South Hold Sound and Little Cayman Beach. Also nearby are Owen Island Beach and Little Cayman Baptist Church.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 16 reviews
Rating 8 - Good. 2 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Madeleine S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family get away
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.
Stayed 3 nights in Mar 2025

10/10 Excellent

Zora L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jan 2020

10/10 Excellent

Todd J., MCLEAN, VIRGINIA, USA

Great place to stay.
Right on the water - wake up to THAT view - amazing. Included bikes, catamaran, paddle boards, kayak, outdoor shower. Trevor picked us up at airport; nice. Walked to town. Walked to Hungry Iguana restaurant and Little Cayman Beach Resort bar/grill. Road our bicycles to Pirates Point; but they picked us up everyday for scuba and brought us back. So easy.
Stayed 5 nights in Dec 2017
This review was submitted before 2018 and has not been verified.

8/10 Good

John L., George Town, Cayman Islands

Beautifully located house with an amazing elevated deck
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.
Stayed 5 nights in Nov 2017

10/10 Excellent

Tom C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
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

10/10 Excellent

Richard Z., Fort Collins, Colorado

Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise Found!
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
Stayed 6 nights in Dec 2019

10/10 Excellent

Chris N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in Dec 2019

10/10 Excellent

Matt T.

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. Thanks!!!!
Stayed 3 nights in Apr 2019

10/10 Excellent

Sue C.

HEAVEN
Every single part of it....sheer heaven.
Stayed 14 nights in Jan 2019

10/10 Excellent

Tom C.

Love it
Why did I come home. Please take me back to Head O Bay absolutely love it there!
Stayed 6 nights in Mar 2018

10/10 Excellent

Shari B.

a wonderful property!
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.
Stayed 4 nights in Mar 2018
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Claudia M.

Great comfortable place to stay.
Great to use the paddle board, bikes and ksyaks. Can watch sunrise from the bed. Close To everything. Beautiful serring
Stayed 8 nights in Feb 2018
This review was submitted before 2018 and has not been verified.

8/10 Good

Robert G., RI

Beautiful Location however a lack of attention to some details
The location on the beach is wonderful, the beds are great, the furniture is comfortable inside and on the porch, and the snorkeling on the island is superb. To offer constructive criticism, the electronics are lacking(no TV the entire stay and the WiFi which is transmitted from another building, requires you to go on the porch to get reliable access and moderate speed). The hot water heater is wired inadequately, requiring resetting the Breaker downstairs often. Trevor responded promptly however the technical nature of the issues were above his capability. He met us at the airport, and was always welcoming.
Stayed 3 nights in Dec 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Kathy E., North Port

Exactly the Vacation We Were Looking For!
Head O Bay is in a wonderful location with easy access to the small town which is about 1 mile away. Kayaks, SUP boards, Catamaran, and Bikes, and small outboard great for scooting to Owen Island all provided. We rented scooters as well just to get to other areas of the island quickly and easily. We prepared most of our meals in the kitchen and enjoyed them on the deck overlooking the Bay! Owen Island is easily reached by Kayak, SUP, or swim. Here you can snorkel, swim, or just enjoy the beach and sun! Blood Bay is easily reached via Bike, Point of Sand easier by Scooter. There are 2 restaurants at the near by resorts within walking distance, a third in town 1 mile away, all enjoyable and with friendly personnel! Everyone was friendly, helpful, and Trevor is the best, you can always find him when needed! It is our hope to return soon with additional family members!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Juli S.

amazing place
Were leaving today and sad to go. This place is amazing and has everything anyone would want and more. Every room has a fabulous view of the bay/ ocean. Its beautifully decorated, clean and well maintained. The location is amazing and the views are fabulous. We enjoyed riding the bikes provided ( we did rent a car but the bike riding was fun) and you can bike ride to the grocery store from the home. They also have Kayaks for you to use and we kayaked to Owens island. There is everything in the kitchen you need to make a fabulous meal, and nice outdoor furniture for al fresco dining. Everyone here was very helpful and we were greeted at the airport by Trevor who showed us around and made us feel like family. I would definatley recommend this home to anyone looking for a fabulous vacation
This review was submitted before 2018 and has not been verified.

10/10 Excellent

William S.

Great stay at Head O' Bay
We had a great stay and a wonderful vacation. This was one of the nicest houses we have rented anywhere in the Caribbean. Snorkeling was outstanding at places like Point of Sand, and a kayak paddle out to Owen Island was like having our own private island. Bonefish were cruising the beach every morning. Trevor was extremely helpful; he took great care of us, and the Rhian family really really put themselves out to assure we had a great vacation.

About the host

Hosted by Owner

Host profile image
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.

Why they chose this property

We built our vacation villa to share the Little Cayman experience with others.

What makes this property 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!

Languages:

English
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