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Old Man Bay Vacation Rentals

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    All 73 Rentals in Old Man Bay
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    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Old Man Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2017
    Wonderful location on quiet north side of island. Beautiful and spacious CLEAN 2nd fl condo with balcony. 3 large bedrooms with bathrooms. Nice TV/dining area. Good sized...
    Reviewed July 27, 2016
    Mark was great from the first email. He sent us a map with the condo location, grocery stores and eateries. He sent me information on a fly fishing guide and all of the fun...
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    About this property
    This small 12-unit Condo resort is situated in the middle of the north coast of Grand Cayman on a bay dotted with coconut palms. 'On the Bay' has a private sandy beach (swimming) cove, large freshwater pool and is a great value for those looking to be close to everything in East End as well as Rum...
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    Old Man Bay, Grand Cayman KY1 1001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Grand Cayman Northern Lights Beachfront Villa1 / 26
    (17)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 December 11, 2017
    Northern lights condo #6 exceeded our expectations- clear water & snorkeling on the reef just in front of the dock. It was an easy drive to starfish bay, rum point...
    Reviewed September 1, 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...
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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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    YOU'VE Arrived! Beachfront 3BR condo w/ Pool-Relax... North Side near Rum Point1 / 23
    (1)Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 27, 2017
    Breathtaking views!. Large, sparkling clean, 3-bedroom condo with full kitchen and laundry; large 2nd-floor patio/deck area. If you are looking for peace and quiet - this is...
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    About this property
    Tranquility in the Tropics is what you'll find at Paradise On the Bay! Come to our well appointed three bedroom beachfront condo and feel at home. Bring your friends, family, or just yourself to our comfortable, airy piece of heaven on Grand Cayman's lush North Side. Rent a car and explore all 22...
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    Old Man Bay, Grand Cayman KY1 1001
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    On The Bay #1041 / 18
    (21)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 2 weeks ago
    Nice quiet location. The condo itself is well maintained and clean. The kitchen is very well provisioned (probably the best of any we have stayed in). Pool is nice. We did...
    Reviewed January 14, 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...
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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 November 6, 2017
    The House was perfect great for a small family. I loved the kitchen and the pool was the perfect size. We will be back next year.
    Reviewed August 4, 2017
    Our family booked this house for our family vacation. Having stayed on SMB 2 other times, we decided that it would be nice to stay on the other side of the island. This decision...
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    About this property
    This exclusive, brand new 3 bedroom beach front villa in North Side, has been beautifully decorated with state of the art fixtures and fittings for your ultimate comfort and convenience. This ultra-modern villa with its sleek design features its own private pool and BBQ, along with two kayaks that...
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    Old Man Bay, Grand Cayman KY1 1001
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 5 miles 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 February 29, 2016
    This was our first time to Grand Cayman Island and we cannot wait to go back. It was breath taking, truly a vacation of a lifetime.We cannot even begin to describe how...
    Reviewed January 22, 2016
    My wife, sister-in-law, and I had a wonderful experience at the Ocean Pearl. Truly remarkable.The condo is right on a sparkling strip of beach. Besides a few sand pipers and...
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    About this property
    Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront villa. Here you can discover the natural side of Grand Cayman, escape your busy life and enjoy peace and tranquility. Part of the Northern Lights development, we are one of just nine units and are bordered by the Salina...
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    Location Information
    North Side, Grand Cayman KY1 0001
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Crescent Beach (Sand) at Half Moon Bay1 / 23
    (10)Excellent
    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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 September 1, 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 January 17, 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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    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 August 25, 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 July 6, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 August 18, 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 July 21, 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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    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 September 19, 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 September 5, 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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    Location Information
    East End, Grand Cayman KY1 1501
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 July 16, 2017
    This is a great place to stay. Quiet and relaxing but close enough to be able to drive to everything we wanted to do. Amazing pools and wonderful ocean view. House was...
    Reviewed June 13, 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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    Location Information
    East End, Grand Cayman KY11801
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 July 5, 2017
    If you aren't into the hustle and bustle of crowds this is the perfect place to stay. My family stayed here for 7 days and couldn't have felt more relaxed. A beautiful quiet...
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    About this property
    A glorious secluded beach and the crystal clear Caribbean provide the backdrop for a dream vacation at The Haven in Cayman Kai. This lovely quiet oceanfront two bedroom, two bath sea lodge (accommodates 6) is located on the North Side of Grand Cayman near Rum Point. At our beach there is swimming,...
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    Location Information
    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Ocean Front Villa with White Sandy Beach1 / 14
    (1)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    This beach front - reef accessible villa was absolutely amazing. The azure waters at our back door were absolutely the most healthy and best snorkeling on the island. (Don't...
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    About this property
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Loft - Casual Living With A Luxurious Twist1 / 24
    (16)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 December 16, 2017
    Our family stayed Dec 9-16, 2017. Beautiful new home on the ocean. Very clean and has everything you need for your home away from home. We could not have chosen a better home...
    Reviewed August 16, 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...
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 4 weeks ago
    If you wind surf this is the place to stay. If you want to be away from the crowds and enjoy the ambiance of the quieter side of the island this place is great. They had kayaks...
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    About this property
    Both beds are QUEEN sized. The Cottage provides basic accommodation, nothing fancy, no marble foyer nor granite countertops, but it does give you spotlessly clean accommodation literally steps from a powdery - white sand beach. We also have a large HOT TUB. On the main floor, you cannot...
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    Location Information
    East End, Grand Cayman KY11801
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,1 / 37
    (6)Very good
    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • Shared Yard
    • Grill
    • Air Conditioning
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We thoroughly enjoyed out stay in a the condo right on the ocean. Everyone was courteous, the property was well-maintained, and we felt very secure. Can't wait to go back!
    Reviewed August 6, 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...
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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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    The Reef Resort - Grand Cayman: Studio, Sleeps 21 / 70
    (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 July 19, 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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    Gorgeous Beachfront Villa, Azure Breeze #51 / 17
    (17)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 4 weeks ago
    Great place. Very relaxing and in a fantastic part of the Island. Snorkeling out front was great. Consistent nice Breeze. Easy to get to many great spots- Kaibo, Rum Point...
    Reviewed December 19, 2017
    Thanks for sharing your amazing house. If you want loud parties with lots of people, noise and a hectic schedule as soon as you walk out of the door this is not the place for...
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    About this property
    Snorkel right outside your villa on the quieter north side of Grand Cayman - where you will enjoy cooling sea breezes (the a/c is often a choice, not a necessity!) and breathtaking uninterrupted views of the ocean. No traffic jams, just the gentle sound of the waves breaking on the reef to lull you...
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    Location Information
    North Side, Grand Cayman KY2 1101
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    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 May 1, 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    Reviewed March 1, 2015
    Island House 17 was a perfect rental property for our vacation. My boyfriend and I traveled with another couple. The house is located in a peaceful community on a beautiful cove...
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    About this property
    Looking for a peaceful, relaxing Caribbean vacation experience in a beautiful beach-front spot that's easy to reach? Come find your slice of paradise at Kai Kotch.  It's a charming 2-bedroom home on a secluded sandy beach in the prime vacation location of the Rum Point / Cayman Kai area of Grand...
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    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
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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
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    • 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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    East End, Grand Cayman 55555
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (25)Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This North Side/Rum Point condo perfectly fit our desire to stay away from the hustle and bustle of Georgetown and the cruise ship traffic. The drive to nearby attractions...
    Reviewed June 8, 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...
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    About this property
    Located in the quiet and secluded Cayman Kai / Rum Point area of Grand Cayman, 'A Mid-Winter Night's Dream' is an ideal place for a tropical getaway. Situated on the ground floor, directly overlooking the ocean, we have great views of the Caribbean from every window. The screened-in lanai is a...
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    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East End
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    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 # 4 Green - Fall Discount 20% Off1 / 7
    (3)Very good
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 5, 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 March 15, 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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    North Side, Grand Cayman KY 1006
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 49
    (10)Excellent
    North Side
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 13, 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 August 5, 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • 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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    Shellen1 / 22
    (12)Very good
    East End
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Waterfront
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 21, 2017
    You cannot beat the location of Shellen. It's set back from the road (cars go about 50 mph so it's good to have some distance) and the privacy and views are fantastic. There...
    Reviewed June 10, 2016
    We stayed at Shellen for a weekend with close friends. It was an amazing property. It exceeded every one of our expectations. Ideal location if you want a quiet tranquil...
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    About this property
    Tuck into your own private mini-resort at Shellen, a 3-bedroom (plus sleeper sofa), 2-bath villa poised at the edge of the rocky, dramatic Caribbean coastline. Amenities include an ocean-view outdoor deck with pool, a sunken hot tub, and plenty of lounge chairs under tall palm trees. Not to mention...
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    East End, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
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    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one steps onto this property the sight, sound of the ocean greets you. This 3 bed, 2 bath charming Cottage, which was once a private home, is tastefully furnished with many personal touches and sits perfectly amongst the landscaped grounds. The owner loves her garden which includes native...
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    North Side, Grand Cayman KY1 1103
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 2015
    Designer Villa and the Grand Cayman, itself, was much more than we expected. The villa is warm and inviting and has everything that a couple, a group or a family would want and...
    Reviewed January 17, 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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    Morritts Tortuga Cayman Islands!! Stingray city, diving, Beautiful Island.1 / 12
    (12)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 November 22, 2017
    We did an exchange via RCI and were very happy with our unit. It was a 2 BR, 2 B unit with a full kitchen. It had just been remodeled and was very nice. However, there in no...
    Reviewed August 19, 2017
    Overall the resort is nice and we had a great view of the ocean from our balcony. The maintenance guy did show up when he was called but our bathroom light was not repaired...
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    About this property
    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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    East End
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Children's Pool
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    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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    Location Information
    East End, Grand Cayman 77777
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Rum Sands1 / 16
    (3)Very good
    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2016
    This was a wonderful spot to stay if you're looking for something away for the crowds and plan on doing your own cooking. The home is surrounded by water and is a perfect getaway.
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    About this property
    Upgrades to this charming one-bedroom, one-bath Rum Sands, located on a quiet cove in Cayman Kai, create both a romantic luxury cottage and a 100% authentic Caymanian escape. Find stainless steel appliances, coastal-chic décor, Caribbean cross-breezes, lots of sunshine and a luxurious king-sized...
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    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean's Edge Grand Cayman Condo1 / 34
    (8)Very good
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
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    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2016
    First the good part. The condo has a great view. The lanai is great, though it would have been nice to have a couch of some sort. I loved the quiet, there was maybe 1 other...
    Reviewed May 27, 2015
    Not only was this condo exactly as described, it exceeded adequate description. You are right on the ocean's edge; I hardly have seen anybody here except occasional visits by...
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    About this property
    Aqua blue ocean views from every window describe the Ocean's Edge. Newly built and located in the exclusive Rum Pointe area of Grand Cayman (the quiet, unspoiled side of Cayman)it is part of a small 10 unit complex with private beach and pool. Located in the exclusive Rum Point, Cayman Kai area...
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    Location Information
    North Side, Grand Cayman XXXXX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Side
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Waterfront
    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled amongst whispering palms on The Cove in the popular Cayman Kai area on the north coast is a comfortable family home that welcomes all! Arranged on two floors this is the perfect ‘home from home’. With 5 bedrooms and 5 bathrooms this beach house makes for the perfect family get-together or...
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    North Side, Grand Cayman KY1 1000
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    East End
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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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    East End, Grand Cayman KY11801
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    East End
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 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 January 17, 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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    North Side
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach Plum Villa is an open floor plan private villa, located directly on a large beach overlooking the multi-colored Caribbean sea. This 2 story expansive home is designed to enjoy the open air breezes and outdoors with a large open deck surrounding the freshwater pool. The North Side of Grand...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Kirk Kove1 / 15
    (8)Very good
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2016
    We stayed a week at the beginning of May at Kirk's Kove and loved this house on the beach. I spent most of my time lying in the hammock on the screened deck reading my book...
    Reviewed April 5, 2014
    My husband and I spent 2 relaxing weeks at Kirk Kove in February. We watched the sun rise from our own private screened in porch, took morning walks down to Starfish Point...
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    About this property
    The spacious layout at Kirk Kove in Cayman Kai will surprise you. A 2-bedroom, 2-bath beach house found on a quiet, protected cove, Kirk Kove offers plenty of space, both indoors and out, for your group to sprawl out and soak up paradise. Outside, you’ll find a setup reminiscent of a beachfront...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, bright and cheerfully decorated beach front house is best for those casual beach lovers and avid snorkelers who enjoy lots of peace and quiet! Perched to embrace the refreshing Caribbean sea breezes and spectacular sea view, a cool tropical cocktail on your sundeck is a must, as well...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Kailypso1 / 24
    (15)Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 3, 2016
    The Kailypso vacation rental was perfect for our needs and the first time we have rented a villa over a timeshare condo. It is a little tight for six adults; however, there are...
    Reviewed April 25, 2015
    This villa was absolutely spectacular! The home was sunny, beautifully decorated, clean, welcoming and made our vacation just perfect. Judy, the manager of Cayman Villas was...
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    About this property
    Friends and families love this 3-bedroom, 2-bath beach house tucked into a private cove in a residential area in Cayman Kai, strolling distance from Rum Point. It’s easy to see what makes Kailypso such a popular beach house for group getaways. It offers the essential ingredients of a Caribbean...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 July 5, 2017
    This newish house is very nice. However, it's easy to see that the upkeep hasn't been as frequent as it needs to be--but it was comfortable none-the-less. The house was always...
    Reviewed February 18, 2017
    Great location for families, friends, right on the beach which is great for snorkeling and costal walks, there are sea urchins so proper footwear needed. Saw plenty of fish...
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    About this property
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 August 18, 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 May 16, 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
    Rental Home - 3 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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    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2017
    Everything looks as advertised. Only issue is the pool never got warm and don't think it's designed to. The ocean was much warmer. Otherwise a perfect place and location. Very...
    Reviewed October 17, 2016
    We had a wonderful peaceful weekend. I’m a local and wanted to try the pools out for a long time as my husband and I usually do staycation every year but mostly in hotels. We...
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    About this property
    Honeymoons and couples getaways find an unforgettable romantic venue at The Pools #12, a one-bedroom, one-bath beachfront condo in Cayman Kai. This exclusive accommodation has its own private swimming pool facing the bright waters of the North Sound, and is within walking distance of two Cayman...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 24, 2017
    We hosted our wedding at Ocean Paradise this past weekend and could not have asked for a better wedding venue! We rented out all 5 homes and our wedding party stayed in them for...
    Reviewed April 9, 2017
    Amazing find with a great location. We stayed in one of the beachfront homes away from the crowds in GeorgeTown. If you like peace and serene environment, you dont need to look...
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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