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Old Man Bay Holiday Rentals

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    All 70 Rentals in Old Man Bay
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    Your Oceanside Retreat Awaits!1 / 17
    (15)Excellent
    Old Man Bay
    2 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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    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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    On The Bay #1041 / 18
    (20)Very good
    Old Man Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2017
    I have been to Cayman many times, first time staying on the North Side. The condo was clean and spacious. The grounds were clean. Pool was great. Beach was nice. We had high...
    Reviewed 22 October 2015
    We stayed at this place over a long weekend just before the start of the tourist season. It was practically empty, very quiet, and hard to find. We actually missed it a couple...
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    About this property
    Tucked into lush tropical landscaping on the ground floor of an intimate beachfront resort, 2-bedroom, 2-bath On The Bay #104 is an ideal alternative to the bustle of Grand Cayman’s more active areas— just 10 minutes from Rum Point. The living is easy here. Head to the private beach and swim in a...
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    Old Man Bay, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Internet Access
    • Grill
    • Washer
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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 its own private pool and BBQ, along with two kayaks that...
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    Old Man Bay, Grand Cayman KY1 1001
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grand Cayman Northern Lights Beachfront Villa1 / 26
    (16)Excellent
    Old Man Bay
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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 1 September 2017
    We are very grateful for the boundless hospitality of Justin and Maureen. We had a great holiday - house is very nice and comfortable. Well-thought interior designs...
    Reviewed 9 June 2017
    We have been coming to cayman for 25 years. Started staying on 7 mile beach until it got to built up and we found this little piece of paradise. This condo is everything a...
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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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    Old Man Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Presenting the Vista Blue Oceanfront Villa. A modern, tropical island style private villa situated on nearly 2 acres of land in quiet, laid back Old Man Bay on Grand Cayman's North side. Vista Blue sits back 1,000 feet from the already sleepy Old Robin Road, offering guests privacy and a...
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    Old Man Bay, Grand Cayman KY
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Old Man Bay.
    No Big Ting - Luxury Beach Villa with a Pool!1 / 34
    (26)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2017
    What a place - right on the white sand beach and the turquoise sea, we loved it. Stock up, drive in and flake out. The house was modern, comfortable and spotlessly...
    Reviewed 6 July 2017
    Awesome place. Very relaxing, full of great extras, very close to Rum Point. Pool overlooking the beach is amazing. Can't wait to come back.
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    About this property
    This renovated three bedroom home in the Rum Point / Cayman Kai area of Grand Cayman has every amenity you could want and now includes a solar heated pool. It has all the luxuries of your home but sits on over a half acre of beach and the back door is steps away from the ocean. The cooling sea...
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 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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    Crescent Beach (Sand) at Half Moon Bay1 / 23
    (10)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Children's Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2017
    We would like to thank Paul and Fay Anne for their generous hospitality during our stay.We loved the house - great location, comfortable and stylish design inside (like Orla...
    Reviewed 17 January 2017
    We have recently returned from a family vacation at Sand with our three young children. Probably the best holiday I’ve ever had – and the accommodation made the difference...
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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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    Coral Loft - Casual Living With A Luxurious Twist1 / 24
    (15)Excellent
    North Side
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Waterfront
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    As soon as we walked in the house our grandchildren were saying "Wow!" at everything. The house is beautiful. Everything is of the highest quality and Bonnie thinks of...
    Reviewed 14 May 2017
    WOW is all I could think when I walked in and saw the wall of windows and the perfect view to the ocean. The home was clean and laid out so there were little gathering spaces...
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    About this property
    This four bedroom beach house underwent a massive renovation in 2013, including the addition of a pool. Coral Loft is on the ocean in the Cayman Kai neighbourhood, a mere mile from the famous Rum Point Beach. The home sits atop a high ridge, offering panoramic views of the ocean as well as the...
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Crescent Beach (Sky) at Half Moon Bay1 / 22
    (5)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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 18 August 2017
    Me and my husband rented both Sand and Sky for our honeymoon. We couldn't have picked a better place! Paul and Faye Ann were wonderful hosts. The beach there is also a beautiful...
    Reviewed 21 July 2017
    House is on the East side of the Island. This is great, after a day of going to the tourist areas. You come back and relax in the the nice quiet atmosphere. House is well kept...
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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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    Amenities & Details
    • Grill
    • Ocean Views
    • Wi-Fi
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    If you aren't into the hustle and bustle of crowds this is the perfect place to stay. My family stayed here for 7 days and couldn't have felt more relaxed. A beautiful quiet...
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    About this property
    A glorious secluded beach and the crystal clear Caribbean provide the backdrop for a dream vacation at The Haven in Cayman Kai. This lovely quiet oceanfront two bedroom, two bath sea lodge (accommodates 6) is located on the North Side of Grand Cayman near Rum Point. At our beach there is swimming,...
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    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Villa on the Caribbean Sea - Stunning Views - Fall & Winter Specials1 / 32
    (2)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 19 September 2017
    Everything was perfect. The house was beautiful, the pool perfect, the view perfect. We saw all kinds of God's creations outside. House was easy to find, yet plenty of...
    Reviewed 5 September 2017
    From the moment you entered the front door and saw the ocean vista right there in front of you to the over-sized and well decorated bedrooms to the FULLY equipped kitchen and...
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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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    East End, Grand Cayman KY1 1501
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, 2450 square foot villa is in a small complex of multi-coloured villas surrounding a gorgeous 5 level cascading swimming pool. All rooms in this villa (except 1 bathroom) face the ocean, allowing you to watch the most beautiful sunrises in the Caribbean, hence the reason we call...
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    Location Information
    East End, Grand Cayman KY11801
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful Ocean Front Villa with White Sandy Beach1 / 14
    (1)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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
    Our piece of paradise looks onto the turquoise waters of the Caribbean Sea, where a coral reef protects this part of the island, and coral heads are scattered for several miles in both directions. Swim in the warm shallow waters and make friends with the local denizens, parrot fish, French grunt,...
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    Location Information
    North Side, Grand Cayman KY1 1700
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayman Calypso Villa1 / 16
    (2)Excellent
    East End
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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 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...
    Reviewed 13 June 2017
    If you want a quiet relaxing vacation rental then this is the one for you. We spent a week at this villa on East End, if only we could have stayed another week. It is away...
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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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    East End, Grand Cayman KY11801
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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
    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
    1 Bedroom, 1 Bathroom, Sleeps 4 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
    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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    East End, Grand Cayman 77777
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a second floor condominium located at Castaways' Cove at The Reef Resort. It is a 1 bedroom unit with a private balcony overlooking the Caribbean where you can enjoy your morning coffee or evening ocean sunset or anything in between. We are steps away from the white sand beach and the...
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    Location Information
    East End, Grand Cayman KY1 1801
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East End
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a second floor condominium located at Castaways' Cove at The Reef Resort. It is a 2 bedroom unit with a private balcony overlooking the Caribbean where you can enjoy your morning coffee or evening ocean sunset or anything in between. We are steps away from the white sand beach and the...
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    Location Information
    East End, Grand Cayman KY1 1801
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,1 / 37
    (5)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Shared Garden
    • Grill
    • Air Conditioning
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2017
    Pretty hard to beat the view!!! Friendly staff. Not so great beds. Internet kept cutting off, which is annoying. Much better than just a hotel room. Low key, and quiet on...
    Reviewed 9 March 2017
    After a little confusion on the stay. Which Marta and her people promptly took care of. Our stay was as fantastic as always. Marta's price was right and there is no way you will...
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    About this property
    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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    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (15)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 May 2017
    My wife and I stayed here for eight days and were more than completely satisfied. The villa is beautifully situated on a white powder beach with the surf just a few feet away...
    Reviewed 22 August 2016
    This was my first trip to GCI. Hard to improve on all the other positive reviews on Frank and this property. Everything I read from others was right on, so I will add comments...
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    About this property
    Snorkel right outside your villa on the quieter north side of Grand Cayman - where you will enjoy cooling sea breezes (the a/c is often a choice, not a necessity!) and breathtaking uninterrupted views of the ocean. No traffic jams, just the gentle sound of the waves breaking on the reef to lull you...
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    Location Information
    North Side, Grand Cayman KY2 1101
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (24)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 8 June 2017
    We had such a great time at Dams place! Everything you could need and great comfort. The ocean is literally 60 feet from the pool. Such a quiet relaxing place. I would recommend...
    Reviewed 31 December 2016
    Our family went to Grand Cayman over Christmas this year. Back in February, 2016, we had booked a condo on the East end of the island. I decided to shoot them a quick email 3...
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    About this property
    Located in the quiet and secluded Cayman Kai / Rum Point area of Grand Cayman, 'A Mid-Winter Night's Dream' is an ideal place for a tropical getaway. Situated on the ground floor, directly overlooking the ocean, we have great views of the Caribbean from every window. The screened-in lanai is a...
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    Location Information
    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Morritts Tortuga Cayman Islands!! Stingray city, diving, Beautiful Island.1 / 12
    (10)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Children's Pool
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 12 July 2017
    We traveled to Morritts the end of June. It was hot, 86f daily average and there was humidity but not unbearable. The ocean breeze made all the difference. The mosquitoes were...
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    About this property
    Secure your spot now for a week of Festivities in 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 shades of blue and...
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    Location Information
    East End, Grand Cayman KY1 1106
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Reef Resort - Grand Cayman: Studio, Sleeps 21 / 35
    (1)Excellent
    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Terrace
    • Grill
    • Hot Tub
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Balcony
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We stayed at The Reef Resort for 7 days. I didn't care for the ocean in this area.Very rocky and dirty but it didn't keep my fiancé from snorkeling every day. I can't wait to...
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    About this property
    The Reef Resort - Grand Cayman: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Fridays, Saturdays, Sundays 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...
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    Location Information
    East End, Grand Cayman KY1 1801
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 49
    (9)Excellent
    North Side
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2016
    We love the north side, and enjoyed this house. The pool is phenomenal and well-situated, both for the view and to avoid getting overheated by afternoon sun. The house was a...
    Reviewed 5 August 2016
    The Ocean Oasis home is located on the quieter, East end of Grand Cayman, and we truly felt like we had our own island getaway. The house and grounds are very spacious and...
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    About this property
    This private residence has opened its doors to become the ultimate vacation rental. The brand new pool is complete and includes a built in bench the entire length of the pool, it is perfect for soaking in the view. Come enjoy all of the comforts of home with the luxury of panoramic ocean views....
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt1 / 48
    (30)Excellent
    North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    Reviewed 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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    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Terrace
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designer decorated spacious Beach House on a gorgeous, white powder sand beach. Two master bedrooms with terraces overlooking the ocean, both with Queen beds, and both with ensuite bathrooms. 3rd bedroom has twin beds and there is a day-bed in the loft. A crib is also available. Stunning...
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    Location Information
    East End, Grand Cayman KY11801
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    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, check in days: Fri, Sat, Sun. Studio, Sleeps 2, with Full Kitchen and/or 1-Bedroom. Sleeps 4 are/may be also available - please inquire about rates and availability....
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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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    Designer Villa, in Tranquil and Beautiful East End1 / 28
    (6)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 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...
    Reviewed 17 January 2015
    Our family had a great time staying here. Our group consistent of me, my 2 year old daughter, my wife, and three of our parents. The setting was beautiful and had plenty of...
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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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    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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    Ocean Paradise Home # 1 Cream - Fall Discount 20% Off1 / 8
    (4)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2017
    This newish house is very nice. However, it's easy to see that the upkeep hasn't been as frequent as it needs to be--but it was comfortable none-the-less. The house was always...
    Reviewed 18 February 2017
    Great location for families, friends, right on the beach which is great for snorkeling and costal walks, there are sea urchins so proper footwear needed. Saw plenty of fish...
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    About this property
    Fall Discount 20% Off Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray City, Rum Point...
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    Location Information
    North Side, Grand Cayman KY1206
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Paradise Home # 5 Yellow - Fall Discount 20% Off1 / 16
    (36)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    We hosted our wedding at Ocean Paradise this past weekend and could not have asked for a better wedding venue! We rented out all 5 homes and our wedding party stayed in them for...
    Reviewed 9 April 2017
    Amazing find with a great location. We stayed in one of the beachfront homes away from the crowds in GeorgeTown. If you like peace and serene environment, you dont need to look...
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    About this property
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY1 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Hot Tub
    • Grill
    • Patio
    • Terrace
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designer decorated spacious Beach House on a gorgeous, private, white powder sand beach. Two master bedrooms with terraces overlooking the ocean, one with a King Bed, the other with a Queen and both with ensuite bathrooms. 3rd bedroom has twin beds and there is a day-bed in the loft. A crib...
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    Location Information
    East End, Grand Cayman KY11801
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Beachfront,Step from Your Porch Onto the Sand1 / 20
    (64)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2017
    This condo is really nice. All the details is a sure sign of proud owners. We enjoyed our stay here.
    Reviewed 29 July 2017
    This condo was completely equipped with everything you could need for a wonderful stay. The owners have really done a wonderful job providing everything needed to make it feel...
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    About this property
    Location: Cayman Kai, North Shore, Grand Cayman, Cayman Islands, Caribbean (Beachfront, Cayman Kai, Kaibo Yacht Club, Rum Point area) Accommodations: Condominium, 2/2, sleeps 6, Cayman Kai Welcome to Blue S'Kai, our white sand beach getaway condo is new to the rental market in beautiful,...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Pools #121 / 11
    (10)Excellent
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    Everything looks as advertised. Only issue is the pool never got warm and don't think it's designed to. The ocean was much warmer. Otherwise a perfect place and location. Very...
    Reviewed 17 October 2016
    We had a wonderful peaceful weekend. I’m a local and wanted to try the pools out for a long time as my husband and I usually do staycation every year but mostly in hotels. We...
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    About this property
    Honeymoons and couples getaways find an unforgettable romantic venue at The Pools #12, a one-bedroom, one-bath beachfront condo in Cayman Kai. This exclusive accommodation has its own private swimming pool facing the bright waters of the North Sound, and is within walking distance of two Cayman...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Front Villa with Superb Views and Own Beach1 / 11
    (7)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2013
    This villa is perfectly placed on the North Side of the island, away from built up busy tourist areas. There is fantastic unspoilt reef a short way into the ocean at the back of...
    Reviewed 16 May 2013
    As you can see in the photos, the six villas at Azure Breeze are located on their own private beach, surrounded by lovely palms and other seaside greenery. Northside is a very...
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    About this property
    Located just 5 miles from Rum Point, directly on the sparkling Caribbean Sea, #2 Azure Breeze Villas is situated in North Side, Grand Cayman. This newly decorated beachside villa has breathtaking panoramic ocean and beach front views from both the ground floor living area as well as from the...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Children's Pool
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, check in days: Fri, Sat, Sun. Studio, Sleeps 2, with Full Kitchen and/or 2-Bedrooms. Sleeps 6 are/may be also available - please inquire about rates and availability. LIVING AREA: Pull Out Sofa, Queen size, Bathtub/Shower BEDROOM: Queen Size Bed KITCHEN FACILITIES: Blender,...
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    Location Information
    East End, Grand Cayman 77777
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rum Haven1 / 16
    (15)Very good
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2017
    Extremely clean (spotless), nicely decorated - would come back in a heartbeat! My sincere appreciation for the effort as my son stayed there to join us at our beach wedding...
    Reviewed 2 January 2017
    We stayed in this unit for a week and loved it. The location is great, steps from Rum Point Beach resort and still quiet and private. Private boat dock and parking in front...
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    About this property
    Escape to Rum Haven for an authentic Caymanian getaway on the banks of Sand Point Cove. This recently redecorated (2017) one-bedroom, one-bath charismatic bungalow is located just steps from iconic Rum Point—which means you can walk to a bustling beach bar, restaurant, and watersports outfitter—not...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Halcyon Days1 / 13
    (2)Very good
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A private pool, sunny décor, your own private boat dock, and a tucked-away location at the end of a tranquil cove make this 2-bedroom cottage in Rum Point a true Caymanian experience. Bring your friends and family! Rum Point is a boater’s destination. At Halcyon Days, the Rum Point Club beach bar,...
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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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    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Internet Access
    • Washer
    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 #9C...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Pools #101 / 14
    (9)Very good
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    Location is amazing, layout of condo is excellent. The property does need a little TLC. The ledge on one of the stairway steps comes right off when you step on it. Really...
    Reviewed 12 January 2016
    We specifically picked this condo because of its distance from Georgetown(an easy 45-50min drive). The area of Cayman Kai is beautiful and the snorkeling is great. Our condo...
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    About this property
    The Pools at Cayman Kai provide an exclusive collection of beachfront condos with a distinguishing perk: your own enclosed, sea-view swimming pool. Spend a day on the white sand beach just outside beyond your back door (or at nearby Rum Point), then return to your 2-bedroom, 2-bath condo and dip...
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    Location Information
    North Side, Grand Cayman KY1 1202
    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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
    • Grill
    • Balcony
    • Children's Pool
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Premier Morritt's Tortuga Club resort offers a luxury beach front paradise atmosphere, with 2 pools a waterfall and swim up cocktail bar. Each air conditioned apartment has a balcony and a fully equipped kitchen. The property's restaurant serves gourmet food and there are several bars. Many...
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    Location Information
    East End, Grand Cayman KY1 1106
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Ocean Paradise Home # 4 Green - Fall Discount 20% Off1 / 7
    (3)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2015
    Lovely place. Really enjoyed our time here, felt like we discovered the best the island has to offer. Owners are very helpful. Cleaning people do a fantastic job! The kitchen...
    Reviewed 15 March 2015
    Best Vacation Spot EverMy wife and I took our family (son, daughter, their spouses and our 15 month old granddaughter) to Grand Cayman to escape the brutal Ohio winter in...
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    About this property
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Kozy Kai - Sealodge #171 / 13
    (17)Very good
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    Beautiful views from bedroom. Enjoy your cheese and wine on the cozy porch overlooking stunning views of amazing blue waters while hearing palm leaves russel in the breezes...
    Reviewed 18 January 2015
    We absolutely loved this place. It was clean,comfortable and right on a beautiful,quiet beach. This unit is the closest to the beach, and has A/C throughout. We mostly used the...
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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 get...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Flip Flop Kai1 / 19
    (1)Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2017
    This was our first trip to the Cayman Island. Our stay at Flip Flop Kai was absolutely perfect. The home was actually better in person then it looked online. We truly enjoyed...
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    About this property
    Welcome to Flip Flop Kai! This beautiful 3 bedroom, 3 bathroom and den villa is nestled on a sandy beach overlooking the bioluminescent Cove in Cayman Kai. This home has gorgeous views from almost every room and a wonderful covered beach side veranda where you can listen to the gentle lapping of...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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