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Old Man Bay Vacation Rentals

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    Travelers to Old Man Bay are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 78 Rentals in Old Man Bay
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    New Listing - 3 Bedroom Ocean Front - Tranquil, Peaceful Location! Snorkeling!1 / 34
    (1)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Ocean Front Villa -New on the Market Available Christmas- New Years -High Season1 / 20
    (2)Excellent
    Old Man Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4BR-Villa Caymanas1 / 31
    (13)Excellent
    Old Man Bay
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point1 / 23
    (1)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 27, 2017
    Breathtaking views!. Large, sparkling clean, 3-bedroom condo with full kitchen and laundry; large 2nd-floor patio/deck area. If you are looking for peace and quiet - this is...
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    About this property
    Tranquility in the Tropics is what you'll find at Paradise On the Bay! Come to our well appointed three bedroom beachfront condo and feel at home. Bring your friends, family, or just yourself to our comfortable, airy piece of heaven on Grand Cayman's lush North Side. Rent a car and explore all 22...
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    Old Man Bay, Grand Cayman KY1 1001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4BR-Christmas Palms1 / 24
    (24)Very good
    Old Man Bay
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2014
    This place was just as the pictures show. My husband went to celebrate our 35th wedding anniversary with our sons (one with wife and our 11 years old granddaughter, the other's...
    Reviewed June 22, 2014
    Just got back from the best vacation we have had in a while. I can't say enough about this house. It was perfect for our family. There were 5 adults and a 7 year old and...
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    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to Christmas Palms! This spectacular villa sits directly oceanfront in Old Man Bay on the north coast. The villa offers luxurious interiors that are...
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    Old Man Bay, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cayman Sands1 / 27
    (12)Excellent
    Old Man Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2016
    This is a fantastic house right on the beach. They provide every single thing you need to have a fabulous stay. The house was immaculate when we arrived. We were a large group...
    Reviewed April 13, 2015
    This property was absolutely great. Well appointed with a great kitchen for entertaining our large group. In addition, we loved the screened outdoor area that allowed for many...
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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Cayman Sands is an oceanfront villa in Old Man Bay along the north coast. This popular villa is one of only 2-3 homes that offer shore scuba-diving off the famous...
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    Old Man Bay, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Villa Esprit1 / 23
    (4)Excellent
    Old Man Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 6, 2017
    The House was perfect great for a small family. I loved the kitchen and the pool was the perfect size. We will be back next year.
    Reviewed August 4, 2017
    Our family booked this house for our family vacation. Having stayed on SMB 2 other times, we decided that it would be nice to stay on the other side of the island. This decision...
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    About this property
    This exclusive, brand new 3 bedroom beach front villa in North Side, has been beautifully decorated with state of the art fixtures and fittings for your ultimate comfort and convenience. This ultra-modern villa with its sleek design features a fully equipped modern kitchen with new appliances,...
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    Old Man Bay, Grand Cayman KY1 1001
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 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 July 27, 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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    Old Man Bay, Grand Cayman KY1 1001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Your Oceanside Retreat Awaits!1 / 17
    (16)Excellent
    Old Man Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 5, 2017
    We just returned from a week in this wonderful condo. It's away from the crowds, so very quiet. Wide open view of the ocean, slept with the window open so that I could just...
    Reviewed April 26, 2017
    Loved the condo and all it had to offer. My husband really appreciated the recliner! Had many little things like water shoes, beach chairs etc. Even some sun tan lotion and...
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    About this property
    Welcome to On The Bay Condo, located on the ocean’s edge in Old Man Bay, Grand Cayman Island. This is a truly private and tranquil resort, with a lovely white sandy beach, private swimming cove, pool and, of course, the magnificent aqua-blue water of the Caribbean all at your convenience. As...
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    Old Man Bay, Grand Cayman KY1 1010
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand Cayman Northern Lights Beachfront Villa1 / 26
    (19)Excellent
    Old Man Bay
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Where to begin...This was our third trip to Grand Cayman. The previous times we stayed on SMB (and loved it). But this year decided to stay on the North Side to explore and...
    Reviewed February 21, 2018
    My husband and I stayed here with my parents for 9 glorious days. The house was lovely, comfortable, impeccably clean, and incredibly well appointed. We enjoy cooking and...
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    About this property
    Northern Lights Condos is a privately owned and operated nine-unit condominium complex situated on the edge of the ocean on Grand Cayman's quiet north coast. The beauty and comfort of these units are only matched by their natural surroundings; 240 feet of sandy beach, a coral reef teeming with...
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    Location Information
    Old Man Bay, Grand Cayman KY1 1201
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Coral Cottage Yellow in Old Man Bay is one of two, charming brand new homes, full of Cayman character, nestled together right on the oceanfront. The cottage has a...
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    Old Man Bay, Grand Cayman KY1 1702
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Coral Cottage Pink in Old Man Bay is one of two charming brand new homes full of Cayman character, nestled together right on the oceanfront. The cottage has a private...
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    Old Man Bay, Grand Cayman KY1 1702
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Old Man Bay
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Waterfront
    • Parking
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Coral Cottages Pink & Yellow consists of two brand new villas, full of Cayman character, nestled together right on the oceanfront in Old Man Bay. Each villa has a...
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    Location Information
    Old Man Bay, Grand Cayman KY1 1702
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    The following rentals are within 5 miles of Old Man Bay.
    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (20)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Certificate of Excellence
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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 February 12, 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 January 25, 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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    Location Information
    North Side, Grand Cayman KY2 1101
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 29, 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 January 22, 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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    Location Information
    North Side, Grand Cayman KY1 0001
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sea Beauty1 / 24
    (13)Excellent
    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 22, 2015
    What an amazing experience! Cathy and Jerry have created the most lovely and thoughtful home away. If you want a sanctuary away from the hoards, this is THE place to go...
    Reviewed March 10, 2015
    This gem of a villa is incredible! My wife and teenage daughter and son stayed here for a week, Feb 17 thru the 24th. We absolutely loved it here. The Villa is extremely well...
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    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to Sea Beauty, a Cayman-style gingerbread cottage located on the island's south coast. Sea Beauty is unique from the other properties we manage in that it has...
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    Location Information
    East End, Grand Cayman KY1 1202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayman Calypso Villa1 / 16
    (3)Excellent
    East End
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
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    Amenities & Details
    • Grill
    • Washer
    • Balcony
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2018
    If your looking for a spacious,quiet, comfortable home away from the cruise tourist..A place to really feel at home..This IS the place to be! We loved our 11 day stay here. The...
    Reviewed July 16, 2017
    This is a great place to stay. Quiet and relaxing but close enough to be able to drive to everything we wanted to do. Amazing pools and wonderful ocean view. House was...
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    About this property
    Our rental villas are situated in the quaint community of East End on Grand Cayman, away from all the noise and congestion of Georgetown and 7-mile beach. Parking is a HUGE problem in Georgetown and on 7 mile beach -- there are very few public parking lots, and many streets do not allow parking....
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    Location Information
    East End, Grand Cayman KY11801
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Private Villa on the Caribbean Sea - Stunning Views - Fall & Winter Specials1 / 32
    (4)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 20, 2018
    We feel so fortunate to have recently had the opportunity to spend 3 glorious weeks at Endless Breeze – our first visit to Grand Cayman.My husband and I are nurses (me...
    Reviewed April 1, 2018
    The house is amazing and located in east end of island away from all the ships and hustle and bustle of the island. The house has every amenity you can think of making your stay...
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    About this property
    Located on the quiet east end of the island, you will find many restaurants and beaches to choose from at this very private home. Cool down and relax on the great pool decking or gazebo. With one of the best views of the ocean facing due-south. You can see terrific sunrises and sunsets and catch an...
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    Location Information
    East End, Grand Cayman KY1 1501
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 61 / 13
    (11)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2015
    We just returned from spending a week at Cayman Stead. Jackie was very prompt to address all my questions prior to our departure, and she provided great information on the area...
    Reviewed March 3, 2015
    We fortunate enough to stay here for two months this winter! This unit has a well equipped kitchen for someone that wants to do a little cooking. The pans are not so thin...
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    About this property
    This luxury vacation condo rental is located on the second floor of the North Pointe Condominium building, which houses only 10 units. Freshly remodeled and decorated, Cayman Stead offers luxury accommodations for your Caribbean Island vacation in paradise! This air-conditioned ocean view condo...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Crescent Beach (Sand) at Half Moon Bay1 / 23
    (14)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other travelers have booked this property
    Certificate of Excellence
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    • Washer
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Children's Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2018
    The apartment was sparkling, with a beautiful kitchen and appliances, comfortable beds, and fabulous views. Loved it!
    Reviewed February 10, 2018
    Hurricane Nate rumbled through the week before we arrived at Crescent Beach, but that did nothing to detract from this beautiful beach. We were steps away from the beach, with...
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    About this property
    Crescent Beach offers very secluded, private and peaceful ocean-front living in a marine park with coral gardens. The beach is semi-private and a home for nesting turtles. The two luxury apartments are called Sky (upper) and Sand (ground). Each apartment accommodates six persons and an optional...
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    Location Information
    East End, Grand Cayman KY1 1501
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Beautiful White Sandy Beach, Low Season Special, pay for 6 nights, stay 7 nights1 / 13
    (2)Very good
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 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
    Special Offer during Low Season (min. 1 week stay) Guest Review: '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....' Our piece of paradise looks onto the turquoise waters of the...
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    Location Information
    North Side, Grand Cayman KY1 1700
    Rental Home - 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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    • Grill
    • Ocean Views
    • Wi-Fi
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 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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    Location Information
    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Morritts Tortuga - Cayman Islands Stingray city, diving, Beautiful Beaches.1 / 12
    (12)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Housekeeping Included
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 22, 2017
    We did an exchange via RCI and were very happy with our unit. It was a 2 BR, 2 B unit with a full kitchen. It had just been remodeled and was very nice. However, there in no...
    Reviewed August 19, 2017
    Overall the resort is nice and we had a great view of the ocean from our balcony. The maintenance guy did show up when he was called but our bathroom light was not repaired...
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    About this property
    Check in Friday, Saturday or Sunday. Weeks only. Get away and experience paradise. This resort offers white sandy beaches and crystal clear waters with a little bit for everyone... for those who want to relax and escape to the adventure seeker. RELAX - White sandy beaches, Ocean with a million...
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    Location Information
    East End, Grand Cayman KY1 1106
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Crescent Beach (Sky) at Half Moon Bay1 / 22
    (7)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other travelers have booked this property
    Certificate of Excellence
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Children's Pool
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2018
    We rented the whole house (Sky & Land) for the week. The privacy, the many extras inside, such as - a welcoming package, bicycles, kayaks, snorkeling equipment, first aid...
    Reviewed January 23, 2018
    This lovely house is easy to find on the east side of the island (approx. 35 min from 7 Mile Beach). The snorkeling in the bay is incredible. I'd recommend bringing or buying...
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    About this property
    Crescent Beach offers very secluded, private and peaceful ocean-front living in a marine park with coral gardens. The beach is semi-private and a home for nesting turtles. The two luxury apartments are called Sky (upper) and Sand (ground). Each apartment accommodates six persons and an optional...
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    Location Information
    East End, Grand Cayman KY1 1501
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Inquiry
    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    1BR/1BA Mahogany Cove Apartment is directly oceanfront in the Cottage District on the south coast in the middle of the island. Offering excellent snorkeling directly behind the house and from the adjacent dock next door, a sandy beach for long walks or a hammock under the thatched cabana for lazy...
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    East End, Grand Cayman KY1 1202
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 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 March 1, 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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    Blue Sea Hideaway1 / 15
    (1)Very good
    East End
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Sea Hideaway is a delightful, 550 square foot studio apartment that is steps from a white sandy beach. Newly built, it has a full size refrigerator, microwave/convection oven, ceramic cooktop and a dishwasher. There is a queen sized bed, sofa and dinette. Just outside the sliding glass...
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    Location Information
    East End, Grand Cayman KY11801
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (27)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 August 15, 2018
    This place has everything you need from kitchen needs to snorkeling gear. Wonderful location -- waking up to beach scenery every morning! Quiet location and close to Rum Point...
    Reviewed March 30, 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...
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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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    Designer Villa, in Tranquil and Beautiful East End1 / 28
    (7)Excellent
    East End
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2018
    Excellent rental with views of the beach! Awesome swimming pools and pool floaties & noodles in the closet. Great large rooms and plenty of bathrooms. We loved our time on...
    Reviewed April 15, 2015
    Designer Villa and the Grand Cayman, itself, was much more than we expected. The villa is warm and inviting and has everything that a couple, a group or a family would want and...
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    About this property
    Divers paradise or just kick back and relax in this Caribbean-style, THREE story villa with media loft & separate office area. This 2450 square foot, designer decorated villa is offers plenty of elbow room with 3+ bedrooms, and 3.5 baths, Located in a small, private and intimate complex of...
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    East End, Grand Cayman 540259
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Ecstasea1 / 25
    (3)Very good
    North Side
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2014
    5BR Ecstasea was an excellent choice for our ten days on the North side this past March, away from the hustle and bustle of Georgetown. Location, water quality, beach access and...
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    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to Ecstasea. This two-story oceanfront villa is located on the north side of the island, approximately a mile east of the Rum Point Club. Nestled on a deep,...
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    North Side, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    'PIECE of MINE' Luxury VIlla1 / 12
    (1)Excellent
    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2018
    Piece of Mine was A GREAT GET AWAY. it is well laid out, immaculately kept as well as well appointed. We enjoyed the location for the exploration of the east end of the island...
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    About this property
    “Piece of Mine” is located in “Cottage” (Frank Sound) on the southeastern coast of Grand Cayman. Enjoy the beach where you can find lots of interesting rocks, shells and other things that wash up daily. The body of water known as “Frank Sound” is protected by a coral reef. You will find some of...
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    East End, Grand Cayman 00000
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to KiToCay! This 3,000 sq. ft. sun-filled home is located in the village of Old Man Bay within walking distance to Over The Edge Restaurant and Bar. The...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Morritt's Tortuga Club - East End, Grand Cayman, Cayman Islands: 2-BR, 2 Baths, Sleeps 6, with Full Kitchen. Fixed week rental, 7 nights blocks only, Friday, Saturday or Sunday check in / changeover only. LIVING AREA: Pull Out Sofa, Queen size, Bathtub/Shower BEDROOM 1: Queen Size Bed BEDROOM...
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    Location Information
    East End, Grand Cayman KY 1 1106
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean's Edge Grand Cayman Condo1 / 34
    (8)Very good
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 November 12, 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 May 27, 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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    Location Information
    North Side, Grand Cayman XXXXX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East End
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
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    • Shared Outdoor Pool (Unheated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 story, 3 bedroom, 3.5 bath private villa with 4 pools just outside the slider. The beach is just across the street inside the reef. Relax under the palm with a breeze blowing in a tropical island setting. The kitchen is fully equipped for preparing your own meals, you can grill your steaks...
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    Location Information
    East End, Grand Cayman KY1800
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oceanfront Ground Floor 2 bedroom 2 bathroom sleeps 4-61 / 28
    (5)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 July 14, 2018
    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 July 12, 2018
    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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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East End
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Washer
    • Hot Tub
    • Patio
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, private 1 bedroom apartment takes up the entire ground floor level of a large 3-storey house in the East End of Grand Cayman. It walks out directly to a stunningly beautiful white, sandy beach, lush with vegetation and palm trees, right on your doorstep. Lounge chairs are on the...
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    Location Information
    East End, Grand Cayman KY11801
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    East End
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Morritts Tortuga Club Resort - East End Grand Cayman: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Saturday check in Studio Poolside Suite Our Grand Cayman Studio suite is poolside with an area of approximately 450 square feet, one minute walk to the beach. Studio suits two, with a...
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    Location Information
    East End, Grand Cayman KY1 1106
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Coco Kai Beach Front Villa -Cayman Kai1 / 21
    (1)Excellent
    North Side
    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 March 9, 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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    Location Information
    North Side, Grand Cayman KY1
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 15
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    Cayman Cottage by the Sea1 / 18
    (1)Very good
    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 27, 2017
    If you wind surf this is the place to stay. If you want to be away from the crowds and enjoy the ambiance of the quieter side of the island this place is great. They had kayaks...
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    About this property
    Both beds are QUEEN sized. The Cottage provides basic accommodation, nothing fancy, no marble foyer nor granite countertops, but it does give you spotlessly clean accommodation literally steps from a powdery - white sand beach. We also have a large HOT TUB. On the main floor, you cannot...
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    Location Information
    East End, Grand Cayman KY11801
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ocean Paradise # 5 Yellow - Affordable Luxury Home w/ pool (Aug - Dec 10-20% Off1 / 16
    (36)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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 May 24, 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 April 9, 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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    Aug - Dec 2018 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Paradise # 1 Cream - Affordable Luxury Home w/ pool (Aug - Dec 10-20% Off)1 / 8
    (4)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 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 February 18, 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
    Aug - Dec 2018 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4BR-Castaway Cove1 / 21
    (3)Very good
    North Side
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to Castaway Cove, an oceanfront villa located in the Northside. Offering excellent snorkeling, this airy, sun-filled two-story beach home features...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    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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    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • 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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    North Side, Grand Cayman KY1 1103
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Ocean Paradise # 3 Blue - Affordable Luxury Home w/ pool (Aug - Dec 10-20% Off1 / 30
    (1)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2017
    Ocean paradise is awesome what u see in the pictures is what u get u only need food and drinks the place is as advertised 5 stars the view is amazing the one minor complaint...
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    About this property
    Aug - Dec 2018 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Kozy Kai - Sealodge #171 / 13
    (19)Very good
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 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 May 22, 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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    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aug - Dec 2018 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 KY11206
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rum Sands1 / 16
    (4)Excellent
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 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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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Pools #121 / 11
    (10)Excellent
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 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 October 17, 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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    Old Man Bay Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
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    85° 77°
    October
    83° 75°
    November
    81° 74°
    December
    80° 73°
    January

    Additional Old Man Bay Info

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