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North Side Holiday Rentals

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    Travellers to North Side are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 39 Rentals in North Side
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    Ocean Pearl Beachfront Townhome Vacation Rental1 / 27
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Beautiful White Sandy Beach, Low Season Special, pay for 6 nights, stay 7 nights1 / 13
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 61 / 13
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 49
    (11)Excellent
    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 1 week ago
    This was the best vacation I've ever had. The home was great for a group of 4, ranging in ages from 11-76. What made this location so special was that it was private and quiet...
    Reviewed 13 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...
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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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    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2018
    View from the Villa in the master bedroom of the Caribbean was outstanding. Very clean nicely furnished and Well supplied. Frank’s preview mailings were of great help.
    Reviewed 25 January 2018
    This villa is comfortable, well equipped, and a good value. It is on the water on the quiet, North Side of Grand Cayman. Just minutes from Rum Point and 40 minutes from George...
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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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    North Side, Grand Cayman KY2 1101
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt1 / 48
    (30)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • 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 1 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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    North Side, Grand Cayman KY1 1105
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/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 30 March 2018
    I just want to say thank you to Dan for going the xtra mile to make sure we had a perfect stay. I had my dates crossed with air and accommodations and Dan worked with us to...
    Reviewed 26 December 2017
    This North Side/Rum Point condo perfectly fit our desire to stay away from the hustle and bustle of Georgetown and the cruise ship traffic. The drive to nearby attractions...
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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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    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean's Edge Grand Cayman Condo1 / 34
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2016
    First the good part. The condo has a great view. The lanai is great, though it would have been nice to have a couch of some sort. I loved the quiet, there was maybe 1 other...
    Reviewed 27 May 2015
    Not only was this condo exactly as described, it exceeded adequate description. You are right on the ocean's edge; I hardly have seen anybody here except occasional visits by...
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    About this property
    Aqua blue ocean views from every window describe the Ocean's Edge. Newly built and located in the exclusive Rum Pointe area of Grand Cayman (the quiet, unspoiled side of Cayman)it is part of a small 10 unit complex with private beach and pool. Located in the exclusive Rum Point, Cayman Kai area...
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    North Side, Grand Cayman XXXXX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand Cayman Sea Lodge Oceanfront on North Side1 / 15
    (1)Excellent
    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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    Halcyon Days1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A private pool, sunny décor, your own private boat dock, and a tucked-away location at the end of a tranquil cove make this 2-bedroom cottage in Rum Point a true Caymanian experience. Bring your friends and family! Rum Point is a boater’s destination. At Halcyon Days, the Rum Point Club beach...
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sea Magic1 / 16
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2016
    We recently vacationed at Sea Magic with our dear friends. Between the two families, there were 3 teenagers, and this was the perfect house for us. There are actually 2 and a...
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    About this property
    This recently renovated 2 bedroom villa has spared no detail. With 2 bedrooms and 2 bathrooms, it is perfect for a couple of friends or a small family who want a Caribbean vacation home that has the quaint character of an islandy cottage - with the luxurious design details of an upscale villa....
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Villa Bellagio1 / 29
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We rented this beautiful home for a family celebration of two "special" birthdays, Father's days for two, and to have an annual epic vacation. This amazing home was...
    Reviewed 8 February 2018
    The house was very comfortable for all 10 of us that stayed, very clean, had enough amenities to last the entire week we were there. We were not able to swim in the bay due to...
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    About this property
    Nestled amongst whispering palms on The Cove in the popular Cayman Kai area on the north coast is a comfortable family home that welcomes all! Arranged on two floors this is the perfect ‘home from home’. With 5 bedrooms and 5 bathrooms this beach house makes for the perfect family get-together...
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    North Side, Grand Cayman KY1 1000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    The Pools #101 / 14
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    Location is amazing, layout of condo is excellent. The property does need a little TLC. The ledge on one of the stairway steps comes right off when you step on it. Really...
    Reviewed 12 January 2016
    We specifically picked this condo because of its distance from Georgetown(an easy 45-50min drive). The area of Cayman Kai is beautiful and the snorkeling is great. Our condo...
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    About this property
    The Pools at Cayman Kai provide an exclusive collection of beachfront condos with a distinguishing perk: your own enclosed, sea-view swimming pool. Spend a day on the white sand beach just outside beyond your back door (or at nearby Rum Point), then return to your 2-bedroom, 2-bath condo and dip...
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    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-61 / 29
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Our stay at this 2 bedroom condo was absoluteley fantastic! The newly renovated ground floor condo has everything you need with the beach at the back door and a infinity pool...
    Reviewed 6 days ago
    If you're looking for a quiet relaxing week, the condo is perfectly located in the Kaibo Yacht Club area; a beautiful large main bedroom with ensuite bathroom, walk in closet...
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    About this property
    Welcome to our recently renovated (2018) and completely updated large two-bedroom, ground floor, oceanfront condo at Kaibo. This small, private 30-unit complex is located away from the cruise ship congestion of Georgetown and the crowds at Seven Mile Beach yet with all the amenities and...
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    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Paradise Home # 5 Yellow - Summer Discount 10-20% Off1 / 16
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    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 9 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
    Summer Discount 10-20% 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...
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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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    Rum Sands1 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    This was a wonderful spot to stay if you're looking for something away for the crowds and plan on doing your own cooking. The home is surrounded by water and is a perfect getaway.
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    About this property
    Upgrades to this charming one-bedroom, one-bath Rum Sands, located on a quiet cove in Cayman Kai, create both a romantic luxury cottage and a 100% authentic Caymanian escape. Find stainless steel appliances, coastal-chic décor, Caribbean cross-breezes, lots of sunshine and a luxurious king-sized...
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    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one steps onto this property the sight, sound of the ocean greets you. This 3 bed, 2 bath charming Cottage, which was once a private home, is tastefully furnished with many personal touches and sits perfectly amongst the landscaped grounds. The owner loves her garden which includes native...
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    Location Information
    North Side, Grand Cayman KY1 1103
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Kaibo Yacht Club #20B1 / 16
    (15)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2018
    Lovely condo at Kaibo Yacht Club. Perfect for two couples. Amazing view from the balcony and steps from the beach. Great pool and hot tub and well kept grounds. Water a little...
    Reviewed 6 November 2017
    Stayed here for 5 days and loved every minute of it . We normally stay on SMB but always wanted to try a few days on the north side. Althgouh it was low season and a couple of...
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    About this property
    A popular boater’s destination and condo complex, Kaibo Yacht Club in Cayman Kai gathers locals and visitors alike, who dock at the Club to grab beachside BBQ, a tropical cocktail, or a gourmet meal. All of these options are available to you, of course—right outside your door at this Kaibo...
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    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Plum Villa1 / 20
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Great house. Very nice layout. All amenities included. We spent a week at the house everything we needed was there. Spent a lot of time outside on beach and around the pool...
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    About this property
    Beach Plum Villa is an open floor plan private villa, located directly on a large beach overlooking the multi-colored Caribbean sea. This 2 story expansive home is designed to enjoy the open air breezes and outdoors with a large open deck surrounding the freshwater pool. The North Side of Grand...
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Pools #121 / 11
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    Everything looks as advertised. Only issue is the pool never got warm and don't think it's designed to. The ocean was much warmer. Otherwise a perfect place and location. Very...
    Reviewed 17 October 2016
    We had a wonderful peaceful weekend. I’m a local and wanted to try the pools out for a long time as my husband and I usually do staycation every year but mostly in hotels. We...
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    About this property
    Honeymoons and couples getaways find an unforgettable romantic venue at The Pools #12, a one-bedroom, one-bath beachfront condo in Cayman Kai. This exclusive accommodation has its own private swimming pool facing the bright waters of the North Sound, and is within walking distance of two Cayman...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Front Villa with Superb Views and Own Beach1 / 11
    (7)Excellent
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Kaibo Yacht Club complex offers more activity and bustle than other accommodations on the island, making it the perfect choice for sociable travelers who love to eat delicious food, mingle, have a few drinks on the beach, and set out for adventures on the water. At 2-bedroom, 2-bath Kaibo...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rum Cove1 / 16
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Waterfront
    • DVD Player
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2014
    This is such a perfect little location. We immediately fell in love with it. So many ammenities. You can use kayaks, bikes, washer/dryer inside, outside shower, a little...
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    About this property
    Bring your sweetheart—and even your dog!—to a lovely, authentic slice of Grand Cayman at one-bedroom, one-bath Rum Cove. This quiet, cove-front bungalow is just across the way from Rum Point, one of Grand Cayman’s most popular areas for mingling, eating delicious grilled food, sipping cocktails,...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Henry's Hideout1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Parking
    • Cable/satellite TV
    • Grill
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    House was beautiful. Very clean had everything you needed as far as beach towels , cooler, beach bag. The kitchen was well equipped and there is a charcoal grill. The deck is...
    Reviewed 4 June 2018
    Gorgeous house. Has everything you would want, and more. Was also one of the cleanest places I have ever stayed in. View spectacular, but be warned that the mosquitoes and...
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    About this property
    This spacious, bright and cheerfully decorated beach front house is best for those casual beach lovers and avid snorkelers who enjoy lots of peace and quiet! Perched to embrace the refreshing Caribbean sea breezes and spectacular sea view, a cool tropical cocktail on your sundeck is a must, as...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kailypso1 / 24
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2016
    The Kailypso vacation rental was perfect for our needs and the first time we have rented a villa over a timeshare condo. It is a little tight for six adults; however, there are...
    Reviewed 25 April 2015
    This villa was absolutely spectacular! The home was sunny, beautifully decorated, clean, welcoming and made our vacation just perfect. Judy, the manager of Cayman Villas was...
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    About this property
    : Friends and families will love this 3-bedroom, 2-bath beach house situated on a secluded cove (Bio Bay), in a residential area in Cayman Kai, strolling distance from the Rum Point Beach Bar and Restaurant It’s easy to see what makes Kailypso such a popular beach house for group getaways. It...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coco Kai Beach Front Villa -Cayman Kai1 / 21
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    • Patio
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2018
    We recently returned home from a wonderful trip to Grand Cayman! There were 3 couples in our group. Coco Kai was the perfect vacation home right on the beach on the North Side...
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    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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    North Side, Grand Cayman KY1
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 15
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    Kozy Kai - Sealodge #171 / 13
    (19)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2018
    The location of Sea Lodge at Cayman Kai is amazing. The location of Kozi Kai within Sea Lodge is just plain incredible. From the back patio, you have a full 180 degree view of...
    Reviewed 22 May 2018
    This one bedroom unit is perfect for 2! The king size bed was so comfortable! The sheets were incredibly soft too. The unit is right on the water's edge, so the views were...
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    About this property
    Romantics will love this 1-bedroom, 1-bath cottage right on the beach in Cayman Kai, less than a 5 minutes’ drive from popular Rum Point. Ocean views from nearly every room and a spacious patio overlooking the water create your own personal paradise. For a very reasonable nightly rate, you can...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Villa La Playa1 / 27
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Washer
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2015
    We stayed at Villa La Playa for 5 nights and had an amazing time. I would definitely recommend this villa to large groups/families, our party was 9 people. The villa itself...
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    About this property
    This authentic Caymanian gem in the quiet residential neighbourhood of Cayman Kai will charm you with its waterfront location, swimming pool, traditional island architecture, distinctive paint colours, and surprisingly spacious interior with 4 bedrooms, 4.5 baths and an open-concept floor plan. All...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Flip Flop Kai1 / 19
    (1)Excellent
    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 29 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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    Rum Haven1 / 16
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2017
    Extremely clean (spotless), nicely decorated - would come back in a heartbeat! My sincere appreciation for the effort as my son stayed there to join us at our beach wedding...
    Reviewed 2 January 2017
    We stayed in this unit for a week and loved it. The location is great, steps from Rum Point Beach resort and still quiet and private. Private boat dock and parking in front...
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    About this property
    Escape to Rum Haven for an authentic Caymanian getaway on the banks of Sand Point Cove. This recently redecorated (2017) one-bedroom, one-bath charismatic bungalow is located just steps from iconic Rum Point—which means you can walk to a bustling beach bar, restaurant, and watersports outfitter—not...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Paradise Home # 4 Green - Summer Discount 10-20% Off1 / 7
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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
    Summer Discount 10-20% 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...
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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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    Ocean Paradise Home # 1 Cream - Summer Discount 10-20% Off1 / 8
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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
    Summer Discount 10-20% 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...
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    Location Information
    North Side, Grand Cayman KY1206
    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 / 35
    (37)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    Our family of five (kids are 19, 16 and 8) enjoyed the best vacation of our lives at this gorgeous oceanfront home. Caymanease is spotless and inviting and very private.I...
    Reviewed 6 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...
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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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    Kaibo Yacht Club #29C1 / 11
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the most popular destinations on Grand Cayman, Kaibo Yacht Club is a haven for boaters, Cayman locals, and visitors. On weekends, boaters dock at the Yacht Club for some excellent beachfront BBQ, tropical cocktails, or a gourmet meal overlooking the sea. And you can stroll to all of this...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront Winter Getaway at Resplendent Kaibo1 / 20
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2018
    I have stayed here twice. The first time on ground level and this year on second level.Much prefer the ground level apt as it is awkward to get suitcases and groceries up the...
    Reviewed 5 January 2018
    This condo is beautiful, clean, and literally steps from the pool and beach! Nikki was so helpful with any questions we had and had great tips for us! Be aware that the...
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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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    Treasure Cove1 / 25
    (10)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2016
    My wife and several of our close friends booked Treasure Cove for couples retreat. We have stayed in hotels for every trip we have ever taken to the Cayman Islands. This was a...
    Reviewed 17 October 2016
    This home is exceptional-beautifully decorated with character beyond most beach rentals, very clean. While you can't swim in the water directly out front (jelly fish everywhere...
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    About this property
    A fantastic place for reunions with friends or family at this secluded, crown-jewel property situated near land’s end beside the calm waters of Cayman Kai. Treasure Cove offers the features that discerning guests expect: from an immaculate private pool to your own boat dock—even two kayaks and a...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
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    Kirk Kove1 / 15
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We stayed a week at the beginning of May at Kirk's Kove and loved this house on the beach. I spent most of my time lying in the hammock on the screened deck reading my book...
    Reviewed 5 April 2014
    My husband and I spent 2 relaxing weeks at Kirk Kove in February. We watched the sun rise from our own private screened in porch, took morning walks down to Starfish Point...
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    About this property
    The spacious layout at Kirk Kove in Cayman Kai will surprise you. A 2-bedroom, 2-bath beach house found on a quiet, protected cove, Kirk Kove offers plenty of space, both indoors and out, for your group to sprawl out and soak up paradise. Outside, you’ll find a setup reminiscent of a beachfront...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    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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    Villa Emmanuel1 / 24
    (8)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2017
    We rented Villa Emmanuel in July 2017 for our family with 3 small children. We couldn't have asked for a better house for our stay. The house was very well equipped (including...
    Reviewed 23 March 2015
    The house was perfect for our family. The beach was great for small kids. The house could use some updating, but overall it was great. Rum Point is a great area and was so...
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    About this property
    Gather your favorite people and head to 5-bedroom, 4-bath Villa Emmanuel, on the quiet shores of Cayman Kai, near Rum Point. A private pool and cabana at the edge of the sea provide the setting for lazy afternoons in the sun—cocktails in hand. When you want to explore the island, you’re in luck:...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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