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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

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

Bedrooms 2
Property type villa
Minimum Stay 1 - 3 nights


About the property

Villa, 2 Bedrooms + Convertible bed(s), 3 Baths (Sleeps 6)

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.

More Details

Member since: 2011
Speaks English
Response time:
Within a day
Response rate:
Calendar last updated:
16 March, 2018

About Owner

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 Blossom Village

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

Guestbook comments from the owner

3 words to describe this peace of Heaven on Earth

1 Peaceful

2 Magnificent

3 Inspiring

(Day 2)

Never once have Tom and I been disappointed! It just keeps getting better and better. So serene, so isolated. The sailboat has really added more enjoyment to our stay! This is truly amazing to find such Happiness and Calmness. Little Cayman is our Home away from Home. From the moment we land it’s our little treasure with pristine beaches and the irresistible call of the Ocean. Thank you for sharing your home with us.

(Day 3) OMG - Really can it be possible - Yes, sailing the best ever. What a fabulous vacation. Sleeping conditions outstanding… Peaceful lapping waters, soft breezes blowing in. Oh my, we are spoiled. I just keep taking picture after picture to plant in my heart. No place on earth - luxury at its finest. Lorraine and Sonny, you two were ahead of your time when you found this spot. Thank you from our hearts, Deb and Tom.
Oct 2013
  • 1 of 5


Accommodation and facilities for this holiday villa on Blossom Village on Cayman Islands

Property Type:
  • villa
  • Self-catering
House Rules:
  • Check-in: 16:00 / Check-out: 11:00
  • Max. occupancy: 6
  • pets considered
  • children welcome ...
Location Type:
  • Beach View
  • Beachfront ...
  • Ocean View
  • Oceanfront
  • Away From It All
  • Family
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Covered Parking
  • Garage
  • Internet
  • Linens Provided
  • Living Room
  • Parking Off Street
  • Telephone ...
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Hob
  • Toaster
  • Dining Area
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 2 Bedrooms, Sleeps 6
  • Books ...
  • CD Player
  • Games ...
  • Balcony ...
  • Bicycles ...
  • Terrace
  • Kayak / Canoe ...
  • Barbecue ...
  • Patio
  • 6 bicycles
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool ...
Onsite Services:
  • Concierge
  • Staff
  • Health/Beauty Spa
  • museums
  • restaurants
Leisure Activities:
  • Boating
  • Shelling
  • Shopping
  • sight seeing
  • Wildlife Viewing
Sports & Adventure Activities:
  • fishing
  • hiking
  • Kayaking
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • swimming
  • water skiing


Excellent! 4.7/5 -
(7 traveller reviews)

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Get Away from it All with a Relaxing Cayman Islands Vacation!
average rating of 4.714286 based on 12 reviews

Great place to stay.

  • 5 of 5

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.

  • Review Submitted: 23-Dec-2017
  • Date of Stay: December 2017
  • Source: VRBO, from HomeAway
Owner's Response: I am so glad y'all had a good time! thank you very much for the good review, I hope y'all will be coming back to stay at Head O' Bay again.
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0 0

Great comfortable place to stay.

  • 5 of 5

Great to use the paddle board, bikes and ksyaks. Can watch sunrise from the bed. Close To everything. Beautiful serring

  • Review Submitted: 05-Mar-2018
  • Date of Stay: February 2018
  • Source: HomeAway
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Beautiful Location however a lack of attention to some details

  • 4 of 5

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.

  • Review Submitted: 12-Dec-2017
  • Date of Stay: December 2017
  • Source: VRBO, from HomeAway
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Beautifully located house with an amazing elevated deck

  • 4 of 5

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.

  • Review Submitted: 15-Nov-2017
  • Date of Stay: November 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the great review, John! It would be our pleasure to have you back at Head O' Bay.
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0 0

Exactly the Vacation We Were Looking For!

  • 5 of 5

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!

  • Review Submitted: 07-May-2016
  • Date of Stay: March 2016
  • Source: VRBO, from HomeAway
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3 0
Morgan Hill,Ca

amazing place

  • 5 of 5

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

  • Review Submitted: 18-Jun-2012
  • Date of Stay: June 2012
  • Source: VRBO, from HomeAway
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4 0


Nearest Airport
1 Miles
The airport is only 1 mile from the villa


Prices & Availability

Prices for this holiday villa on Blossom Village, Caribbean

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
High Season
16 Dec 2017 - 30 Apr 2018
3 night minimum stay
for 3 nights

Additional pricing information

Cleaning fee £108.31
Tax Rate 13.0%

If staying less than one week, add $150.00 cleaning fee.

Owner's Cancellation Policy

  • 50% refund for cancellations more than 7 days before check-in date.
  • 100% refund for cancellations more than 14 days before check-in date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Ask Owner a Question