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Old Man Bay Holiday Rentals

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    Travellers to Old Man Bay are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 92 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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    Truly Oceanfront luxury in Grand Cayman1 / 12
    (44)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Christmas Palms by Grand Cayman Villas and Condos1 / 24
    (24)Very good
    Old Man Bay
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 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 22 June 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
    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 complemented by beautiful multi-windowed views, an oceanfront freshwater pool, and--of course--excellent snorkeling just steps off the pool...
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    Old Man Bay, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Villa Caymanas by Grand Cayman Villas and Condos1 / 31
    (13)Excellent
    Old Man Bay
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2016
    OMG this place was so amazing, we didn't even consider this place initially because several of the pictures do it no justice at all and were not very appealing. Please don't let...
    Reviewed 13 March 2014
    Villa Caymanas is a lovely house right on the beach and is privately situated among landscaping and vegetation. The property is as described. Because it is on the North of the...
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    About this property
    Welcome to Villa Caymanas! This beautiful oceanfront villa is located in Old Man Bay along the north coast. Boasting four full king suites, an oceanfront freshwater pool, and expansive balcony, Villa Caymanas is the perfect vacation retreat. Whether you prefer to explore the snorkeling reefs...
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    Old Man Bay, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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 Garden
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 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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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the crowds of Seven Mile Beach for this peaceful North Side oasis in Grand Cayman.  Welcome to Northern Lights, a 9-unit complex of privately owned two-story townhomes nestled in Old Man Bay, along the quiet north shore.  Northern Lights #5 is one of the few 3 bedroom units within the...
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    Old Man Bay, Grand Cayman KY1 1702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cayman Sands by Grand Cayman Villas and Condos1 / 27
    (12)Excellent
    Old Man Bay
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 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 13 April 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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    About this property
    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 Cayman Wall. With an open, one-story design, Cayman Sands offers guests an intimate experience across 4,000 sq ft. of living space, plus...
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    Old Man Bay, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coral Cottage Pink in Old Man Bay is one of two charming brand new homes full of Cayman flair, nestled together right on the oceanfront. The cottage has a private oceanfront infinity pool and fantastic screened garden atrium. The vistas across the oceanfront and into the garden are spectacularly...
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    Old Man Bay, Grand Cayman KY1 1702
    Holiday Rental House - 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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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 November 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 26 April 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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    Location Information
    Old Man Bay, Grand Cayman KY1 1010
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 private oceanfront infinity pool and fantastic screened garden atrium. The vistas across the oceanfront and into the garden are...
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    Old Man Bay, Grand Cayman KY1 1702
    Holiday Rental House - 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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    • Parking
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 private oceanfront infinity pool and fantastic screened garden atrium. The vistas across the oceanfront and into the gardens are...
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    Location Information
    Old Man Bay, Grand Cayman KY1 1702
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Grand Cayman Northern Lights Beachfront Villa1 / 26
    (20)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 28 October 2018
    My recent stay at the Northern Lights condos was simply amazing. It was my first time visiting Cayman and I wouldn't hesitate in staying here again. I got in late on a Saturday...
    Reviewed 1 October 2018
    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...
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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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    Old Man Bay, Grand Cayman KY1 1201
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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 6 November 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 4 August 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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    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Old Man Bay.
    Ocean Pearl Beachfront Townhome Vacation Rental1 / 27
    (2)Excellent
    North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 February 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 22 January 2016
    My wife, sister-in-law, and I had a wonderful experience at the Ocean Pearl. Truly remarkable.The condo is right on a sparkling strip of beach. Besides a few sand pipers and...
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    About this property
    Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront villa. Here you can discover the natural side of Grand Cayman, escape your busy life and enjoy peace and tranquility. Part of the Northern Lights development, we are one of just nine units and are bordered by the Salina...
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    Location Information
    North Side, Grand Cayman KY1 0001
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sea Beauty by Grand Cayman Villas and Condos1 / 24
    (15)Excellent
    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This place exceeded our expectations by tons. Cathy met us at the house and welcomed us with open arms. A lovely welcome basket with goodies and fresh fruit also awaited us...
    Reviewed 2 weeks ago
    Our two week stay at Sea Beauty was perfect! Cathy met us there and welcomed us to this wonderful delight. The house is as beautiful as the pictures show, no surprises at all...
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    About this property
    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 over 300-feet of private beach! Plus, it's also ADA accessible with wheelchair ramps along the front, extra wide doorways,...
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    Location Information
    East End, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Children's Pool
    • Hot Tub
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Reef Resort - Grand Cayman: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Saturdays check in only. Two Bedroom Master Suite The resort's Grand Cayman Two Bedroom Master Suite, which comfortably sleep six people, is beachfront with an area of approximately 1,350 square feet, plus...
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    Location Information
    East End, Grand Cayman 55555
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 31 March 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 3 March 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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    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (20)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
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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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    Location Information
    North Side, Grand Cayman KY2 1101
    Holiday Rental House - 3 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
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    • Grill
    • Washer
    • Balcony
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 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 16 July 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
    Holiday Rental House - 3 Bedrooms, 2 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 14 July 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 12 July 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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    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 homeowner of this unique 2-story villa owns the adjacent lots as well. Both vacant lots are maintained and shielded from the road with...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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 travellers have booked this property
    Certificate of Excellence
    Check in Check out
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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 15 April 2018
    The apartment was sparkling, with a beautiful kitchen and appliances, comfortable beds, and fabulous views. Loved it!
    Reviewed 10 February 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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    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 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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    Location Information
    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 travellers have booked this property
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Children's Pool
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 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 24 January 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
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Balcony
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mahogany Cove Apartment is directly oceanfront in the Cottage District along the south coast in the middle of the island. Offering excellent snorkeling and a sandy beach for long walks, or a thatched hammock cabana right on the beach for lazy afternoons, this apartment is a perfect couple’s...
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    East End, Grand Cayman KY1 1202
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Castaway Cove by Grand Cayman Villas and Condos1 / 21
    (3)Very good
    North Side
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Castaway Cove, an oceanfront villa located in the Northside. Offering excellent snorkeling, this airy, sun-filled two-story beach home features breathtaking views from almost every room, vaulted ceilings, and an open concept design. Enjoying a protective coral reef, Castaway Cove is...
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conch'ed Out is a sparkling oceanfront cottage in Old Man Bay along the north coast. This Caribbean-style 2 bedroom private villa offers excellent snorkeling steps off the oceanfront pool. A sandy private backyard trails down to a pebbly beach. Five pairs of french doors and screened porches,...
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful White Sandy Beach. Weekly Special: Stay 7 nights pay only for 6 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 14 June 2017
    This beach front - reef accessible villa was absolutely amazing. The azure waters at our back door were absolutely the most healthy and best snorkeling on the island. (Don't...
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    About this property
    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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    North Side, Grand Cayman KY1 1700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,1 / 37
    (8)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • Shared Garden
    • Grill
    • Air Conditioning
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    Booked and payed for a 2 week vacation at the wyndam, at the end of the first week we were told we had to move due to booking error, we had to move to a different resort, we...
    Reviewed 30 January 2018
    Loved the condo - view just stunning. Condo had everything we needed and the beach was awesome . Very windy for most of our stay so made it quite noisy during the night...
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    The Reef Resort - Grand Cayman: 1-BR, Sleeps 4, with Full Kitchen. Fixed week - 7 nights, Saturdays check in only. One Bedroom Executive Suite The resort's One Bedroom Suite at the Reef is among the best in the Cayman Islands. It is beachfront and sleep up to four guests with an area of...
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    Location Information
    East End, Grand Cayman KY1 1801
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Mahogany Cove by Grand Cayman Villas and Condos1 / 19
    (4)Very good
    East End
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • Ocean Views
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2016
    Wife and I stayed 8 nights in the lower one bedroom villa portion of Mahogany Cove. The location was ideal for us as we are avid snorkelers and prefer the quieter side of the...
    Reviewed 10 April 2016
    This was the 3rd time we have stayed at Mahogany Cove and we are definitely planning on coming back for a 4th! This place has everything you need; GREAT SNORKELING, GREAT...
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    About this property
    Mahogany Cove is directly oceanfront in the Cottage District, on the south coast in the middle of the island. Featuring a uniquely flexible floor plan, Mahogany Cove can be rented in multiple configurations to suit anyone from honeymooning couples to large family trips and group getaways....
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    East End, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Calypso Blue by Grand Cayman Villas and Condos1 / 28
    (5)Excellent
    North Side
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2016
    Stayed at the newly renovated Calypso blue with 9 other adults. Plenty of room for everyone to join together, or to be off on their own comfortably. The beach was amazing, with...
    Reviewed 6 April 2016
    Most amazing vacation ever!!!! This house is PERFECT. (We had 2 families with 4 kids total, ages 10-13.)I don't even know where to start. The location is great. It's close...
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    About this property
    Calypso Blue has been fully renovated and redecorated, but is still at a reasonable cost for a larger family. Oceanfront freshwater pool with a sandy beach area lead to excellent coral reef snorkeling just steps from the back door. A large oceanfront screened porch is the perfect place to dine or...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    East End
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wyndham Reef Resort: Studio, Sleeps 2, with Kitchenette1 / 39
    (2)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2018
    The view is worth the trip. Awake daily and set on the veranda and enjoy the Caribbean sea. The room is functional and the bed was super comfortable. The only negative I can...
    Reviewed 1 January 2018
    The price was really competitive against others in the area. Staying during the busy season is really expensive and we were glad to find this place which offered a kitchenette...
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    About this property
    Wyndham Reef Resort: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Saturdays check in only. Studio Beach Suite Our Grand Cayman Studio suite is beachfront with an area of approximately 450 square feet, including its own balcony. Studio suits two, with a king size bed overlooking the...
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    East End, Grand Cayman KY1 1801
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Designer Villa, in Tranquil and Beautiful East End1 / 84
    (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 1 May 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 15 April 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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    Location Information
    East End, Grand Cayman 540259
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Ocean Views
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Babylon Reef, a freshly renovated oceanfront villa, with sundeck and private pool, situated directly on one of the best shallow snorkeling sites on the entire island. Protected by a coral reef, there are rarely any currents or waves to contend with so children can play in the shallows...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 15 August 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 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...
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    About this property
    Located in the quiet and secluded Cayman Kai / Rum Point area of Grand Cayman, 'A Mid-Winter Night's Dream' is an ideal place for a tropical getaway. Situated on the ground floor, directly overlooking the ocean, we have great views of the Caribbean from every window. The screened-in lanai is a...
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    Location Information
    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Morritt's Tortuga Club: Studio, Sleeps 2, Full Kitchen1 / 96
    (1)Excellent
    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Children's Pool
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2018
    This place is very nice. Needs some updating, but very clean and ALL staff are incredibly friendly and helpful. The grounds are beautiful and clean. Our only complaint is that...
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    About this property
    Morritt's Tortuga Club - East End, Grand Cayman, Cayman Islands: Studio, Sleeps 2, with Full Kitchen. Fixed week rental, check in days: Fri, Sat, Sun. 1-Bedroom, Sleeps 4, with Full Kitchen and/or 2-Bedrooms. Sleeps 6 are also available - please inquire about rates and availability. Queen Size...
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    Location Information
    East End, Grand Cayman 77777
    Condo/Apartment - 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 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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    Location Information
    North Side, Grand Cayman KY1 1105
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    • Parking
    • Grill
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 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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    Location Information
    East End, Grand Cayman 00000
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cayman Castle & Guesthouse by Grand Cayman Villas and Condos1 / 27
    (4)Excellent
    East End
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2015
    We had a great time. The house was unique and suited our needs. It was in excellent condition and everything worked well. We had no issues. The booking was easy and...
    Reviewed 20 June 2014
    June 7-14, 2014. Every other year we take a "family" vacation..large group of 19.. Ages ranging from 65-1. After much research The Castle was just what I was looking...
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    About this property
    Cayman Castle and Guesthouse sits directly oceanfront on a private 2-acre walled estate. Perched on an elevated point of land, the Cayman Castle grounds include an attached private white sandy beach with excellent snorkeling and sunbathing. Infinity pool (heated in the winter), multi-tiered...
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    Location Information
    East End, Grand Cayman KY 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    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
    Holiday Rental House - 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 22 November 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 19 August 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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    Blue Sea Hideaway1 / 15
    (1)Very good
    East End
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Patio
    • Grill
    • Washer
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    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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    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Waterfront
    • Washer
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cheerfully decorated small resort of oceanfront villas is perfectly located to take advantage of the fresh sea breezes and a magnificent view of the shimmering Caribbean sea. It has a sandy & rocky beach and the snorkeling in front of the villas is fantastic. It's about a 35 minute drive from...
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    Location Information
    North Side, Grand Cayman KY
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rum Haven1 / 16
    (15)Very good
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • 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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    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
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 December 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated 2-Storey villa with 3 bedrooms, 2 of them with ensuite bathrooms. There is also a 2 piece powder room. Configuration is: King Bed, Queen Bed (for some reason trip advisor does not list this as an option) and 2 twin beds on the main floor. The master has the ensuite...
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    Location Information
    East End, Grand Cayman KY1 1801
    Holiday Rental House - 3 Bedrooms, 3 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
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Ocean Views
    • Patio
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lone Palm! Nestled in Gun Bay along the East End, Lone Palm is a 3 bedroom, 3 bathroom award-winning home designed by renowned architect John Doak. An open concept living area with vaulted ceilings opens up to a full-width beachfront veranda with a private pool, sundeck, and a white...
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    Location Information
    East End, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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