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Old Man Bay Holiday Homes

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    Don't let other travellers get your favourite Old Man Bay area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 23 Rentals in Old Man Bay
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    Your Oceanside Retreat Awaits!1 / 17
    (14)Excellent
    Old Man Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Grand Cayman Northern Lights Beachfront Villa1 / 26
    (16)Excellent
    Old Man Bay
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    On The Bay - North Side Beachfront 3BR, 3Bath Condo - near Rum Point1 / 23
    (1)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Truly Oceanfront luxury in Grand Cayman1 / 12
    (44)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2017
    Wonderful location on quiet north side of island. Beautiful and spacious CLEAN 2nd fl condo with balcony. 3 large bedrooms with bathrooms. Nice TV/dining area. Good sized...
    Reviewed 28 July 2016
    Mark was great from the first email. He sent us a map with the condo location, grocery stores and eateries. He sent me information on a fly fishing guide and all of the fun...
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    About this property
    This small 12-unit Condo resort is situated in the middle of the north coast of Grand Cayman on a bay dotted with coconut palms. 'On the Bay' has a private sandy beach (swimming) cove, large freshwater pool and is a great value for those looking to be close to everything in East End as well as Rum...
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    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Old Man Bay.
    Ocean Pearl Beachfront Townhome Vacation Rental1 / 27
    (2)Excellent
    North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2016
    This was our first time to Grand Cayman Island and we cannot wait to go back. It was breath taking, truly a vacation of a lifetime.We cannot even begin to describe how...
    Reviewed 23 January 2016
    My wife, sister-in-law, and I had a wonderful experience at the Ocean Pearl. Truly remarkable.The condo is right on a sparkling strip of beach. Besides a few sand pipers and...
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    About this property
    Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront villa. Here you can discover the natural side of Grand Cayman, escape your busy life and enjoy peace and tranquility. Part of the Northern Lights development, we are one of just nine units and are bordered by the Salina...
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    North Side, Grand Cayman KY1 0001
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    No Big Ting - Luxury Beach Villa with a Pool!1 / 34
    (26)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    What a place - right on the white sand beach and the turquoise sea, we loved it. Stock up, drive in and flake out. The house was modern, comfortable and spotlessly...
    Reviewed 7 July 2017
    Awesome place. Very relaxing, full of great extras, very close to Rum Point. Pool overlooking the beach is amazing. Can't wait to come back.
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    About this property
    This renovated three bedroom home in the Rum Point / Cayman Kai area of Grand Cayman has every amenity you could want and now includes a solar heated pool. It has all the luxuries of your home but sits on over a half acre of beach and the back door is steps away from the ocean. The cooling sea...
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    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coral Loft - Casual Living With A Luxurious Twist1 / 24
    (15)Excellent
    North Side
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Waterfront
    • Ocean Views
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    As soon as we walked in the house our grandchildren were saying "Wow!" at everything. The house is beautiful. Everything is of the highest quality and Bonnie thinks of...
    Reviewed 15 May 2017
    WOW is all I could think when I walked in and saw the wall of windows and the perfect view to the ocean. The home was clean and laid out so there were little gathering spaces...
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    About this property
    This four bedroom beach house underwent a massive renovation in 2013, including the addition of a pool. Coral Loft is on the ocean in the Cayman Kai neighbourhood, a mere mile from the famous Rum Point Beach. The home sits atop a high ridge, offering panoramic views of the ocean as well as the...
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    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beautiful Ocean Front Villa with White Sandy Beach1 / 14
    (1)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    This beach front - reef accessible villa was absolutely amazing. The azure waters at our back door were absolutely the most healthy and best snorkeling on the island. (Don't...
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    About this property
    Our piece of paradise looks onto the turquoise waters of the Caribbean Sea, where a coral reef protects this part of the island, and coral heads are scattered for several miles in both directions. Swim in the warm shallow waters and make friends with the local denizens, parrot fish, French grunt,...
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    Location Information
    North Side, Grand Cayman KY1 1700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand Cayman Sea Lodge Oceanfront on North Side1 / 15
    (1)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Ocean Views
    • Wi-Fi
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    If you aren't into the hustle and bustle of crowds this is the perfect place to stay. My family stayed here for 7 days and couldn't have felt more relaxed. A beautiful quiet...
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    About this property
    A glorious secluded beach and the crystal clear Caribbean provide the backdrop for a dream vacation at The Haven in Cayman Kai. This lovely quiet oceanfront two bedroom, two bath sea lodge (accommodates 6) is located on the North Side of Grand Cayman near Rum Point. At our beach there is swimming,...
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    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (15)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    My wife and I stayed here for eight days and were more than completely satisfied. The villa is beautifully situated on a white powder beach with the surf just a few feet away...
    Reviewed 22 August 2016
    This was my first trip to GCI. Hard to improve on all the other positive reviews on Frank and this property. Everything I read from others was right on, so I will add comments...
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    About this property
    Snorkel right outside your villa on the quieter north side of Grand Cayman - where you will enjoy cooling sea breezes (the a/c is often a choice, not a necessity!) and breathtaking uninterrupted views of the ocean. No traffic jams, just the gentle sound of the waves breaking on the reef to lull you...
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    Location Information
    North Side, Grand Cayman KY2 1101
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront,Step from Your Porch Onto the Sand1 / 20
    (64)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    This condo is really nice. All the details is a sure sign of proud owners. We enjoyed our stay here.
    Reviewed 30 July 2017
    This condo was completely equipped with everything you could need for a wonderful stay. The owners have really done a wonderful job providing everything needed to make it feel...
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    About this property
    Location: Cayman Kai, North Shore, Grand Cayman, Cayman Islands, Caribbean (Beachfront, Cayman Kai, Kaibo Yacht Club, Rum Point area) Accommodations: Condominium, 2/2, sleeps 6, Cayman Kai Welcome to Blue S'Kai, our white sand beach getaway condo is new to the rental market in beautiful,...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Paradise Home # 4 Green - Fall Discount 20% Off1 / 7
    (3)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2015
    Lovely place. Really enjoyed our time here, felt like we discovered the best the island has to offer. Owners are very helpful. Cleaning people do a fantastic job! The kitchen...
    Reviewed 15 March 2015
    Best Vacation Spot EverMy wife and I took our family (son, daughter, their spouses and our 15 month old granddaughter) to Grand Cayman to escape the brutal Ohio winter in...
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    About this property
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (24)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2017
    We had such a great time at Dams place! Everything you could need and great comfort. The ocean is literally 60 feet from the pool. Such a quiet relaxing place. I would recommend...
    Reviewed 31 December 2016
    Our family went to Grand Cayman over Christmas this year. Back in February, 2016, we had booked a condo on the East end of the island. I decided to shoot them a quick email 3...
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    About this property
    Located in the quiet and secluded Cayman Kai / Rum Point area of Grand Cayman, 'A Mid-Winter Night's Dream' is an ideal place for a tropical getaway. Situated on the ground floor, directly overlooking the ocean, we have great views of the Caribbean from every window. The screened-in lanai is a...
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    Location Information
    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 49
    (9)Excellent
    North Side
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 2016
    We love the north side, and enjoyed this house. The pool is phenomenal and well-situated, both for the view and to avoid getting overheated by afternoon sun. The house was a...
    Reviewed 6 August 2016
    The Ocean Oasis home is located on the quieter, East end of Grand Cayman, and we truly felt like we had our own island getaway. The house and grounds are very spacious and...
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    About this property
    This private residence has opened its doors to become the ultimate vacation rental. The brand new pool is complete and includes a built in bench the entire length of the pool, it is perfect for soaking in the view. Come enjoy all of the comforts of home with the luxury of panoramic ocean views....
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt1 / 48
    (30)Excellent
    North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    Reviewed 2 March 2015
    Island House 17 was a perfect rental property for our vacation. My boyfriend and I traveled with another couple. The house is located in a peaceful community on a beautiful cove...
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    About this property
    Looking for a peaceful, relaxing Caribbean vacation experience in a beautiful beach-front spot that's easy to reach? Come find your slice of paradise at Kai Kotch.  It's a charming 2-bedroom home on a secluded sandy beach in the prime vacation location of the Rum Point / Cayman Kai area of Grand...
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    Location Information
    North Side, Grand Cayman KY1 1105
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean Front Villa with Superb Views and Own Beach1 / 22
    (7)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2013
    This villa is perfectly placed on the North Side of the island, away from built up busy tourist areas. There is fantastic unspoilt reef a short way into the ocean at the back of...
    Reviewed 16 May 2013
    As you can see in the photos, the six villas at Azure Breeze are located on their own private beach, surrounded by lovely palms and other seaside greenery. Northside is a very...
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    About this property
    Located just 5 miles from Rum Point, directly on the sparkling Caribbean Sea, #2 Azure Breeze Villas is situated in North Side, Grand Cayman. This newly decorated beachside villa has breathtaking panoramic ocean and beach front views from both the ground floor living area as well as from the...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Paradise Home # 1 Cream - Fall Discount 20% Off1 / 8
    (4)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2017
    This newish house is very nice. However, it's easy to see that the upkeep hasn't been as frequent as it needs to be--but it was comfortable none-the-less. The house was always...
    Reviewed 18 February 2017
    Great location for families, friends, right on the beach which is great for snorkeling and costal walks, there are sea urchins so proper footwear needed. Saw plenty of fish...
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    About this property
    Fall Discount 20% Off Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray City, Rum Point...
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    Location Information
    North Side, Grand Cayman KY1206
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Paradise Home # 5 Yellow - Fall Discount 20% Off1 / 16
    (36)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    We hosted our wedding at Ocean Paradise this past weekend and could not have asked for a better wedding venue! We rented out all 5 homes and our wedding party stayed in them for...
    Reviewed 10 April 2017
    Amazing find with a great location. We stayed in one of the beachfront homes away from the crowds in GeorgeTown. If you like peace and serene environment, you dont need to look...
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    About this property
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY1 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Caymanease An Oceanfront Home on a Private Beach with a Pool and Kayaks1 / 33
    (36)Excellent
    North Side
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    My husband and I booked the Caymanese for our family to celebrate our oldest daughter's college graduation. We enjoyed every minute of our stay! The Caymanese is a beautiful...
    Reviewed 25 March 2017
    Fabulous beach home that the owners obviously take pride in. And I emphasize home - not just your standard rental. - It is immaculately clean, beautifully decorated, and...
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    About this property
    Caymanease is a private, oceanfront home with a pool sitting on a secluded, private sandy beach located in the North Side of Grand Cayman. This villa sleeps 8 and offers 3 bedrooms and 3 and 1/2 baths, and enclosed outdoor shower, an oceanfront pool, kayaks and all the amenities you need to have a...
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    Location Information
    North Side, Grand Cayman KY1 1107
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    North Side
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Parking
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience pure beach life tranquility at ‘Conquered Fame,’ a 4-bedroom, 2-bathroom beachfront vacation rental villa in the Cayman Islands. Situated on half an acre in the peaceful Rum Point area of Cayman Kai, this 1,500 square foot home comfortably sleeps 10, and offers an amazing open-layout,...
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    Location Information
    North Side, Grand Cayman KY1 1700
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Flip Flop Kai1 / 19
    (1)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2017
    This was our first trip to the Cayman Island. Our stay at Flip Flop Kai was absolutely perfect. The home was actually better in person then it looked online. We truly enjoyed...
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    About this property
    Welcome to Flip Flop Kai! This beautiful 3 bedroom, 3 bathroom and den villa is nestled on a sandy beach overlooking the bioluminescent Cove in Cayman Kai. This home has gorgeous views from almost every room and a wonderful covered beach side veranda where you can listen to the gentle lapping of...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    North Side
    6 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    • Patio
    • Satellite TV
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The immensely popular Coco Kai Villa is now available directly from the owner. This property is situated in the quiet, pristine area of Cayman Kai. Our home also has an in-ground pool and sits on the beautiful beaches of the Caribbean. This is a very private, exclusive part of beautiful Grand...
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    Location Information
    North Side, Grand Cayman KY1
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 15
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    Beachfront Winter Getaway at Resplendent Kaibo1 / 20
    (4)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Waterfront
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2014
    We loved stay. This is our 7th trip to Cayman and we have never stayed in the same place twice. Next year we will be staying here again and many years to come. The location...
    Reviewed 13 April 2014
    My husband and I and our two young boys (3 & 5) stayed at this condo for almost a week. It was perfect and I'm so glad we booked this one. The condo itself was nicely laid...
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    About this property
    Located at the Kaibo Yacht Club Phase 2 in Grand Cayman's exclusive Cayman Kai area, this is a 2 bedroom/2 bathroom condo, recently refurbished and fully equipped. Sleeps up to 6 persons, with king size bed in master bedroom, full size bed in second bedroom and has a queen-sized sofa bed in living...
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    Location Information
    North Side, Grand Cayman KY11007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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