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Cayman Islands Romantic Vacation Rentals

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    123 Matching Rentals in Cayman IslandsView all 371 rentals
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    2 BR MoonLight Kai condo at Kaibo Yacht Club, ph.21 / 27
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The Reef Resort - Grand Cayman: Studio, Sleeps 21 / 35
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Escape from Reality - Ocean Front!1 / 47
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Balcony
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2018
    Absolutely fantastic place. Well furnished. Clean. Well located. Will be back. The only advise is the beds were to small
    Reviewed February 5, 2018
    I have rented scores of vacation homes in many locations and I have to say this was my favorite of all time. Comfy, cozy, and had everything we needed for a wonderful vacation...
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    About this property
    Hear and see the ocean in this beautiful, newly remodeled 1500 Sq. Ft, two bedroom beach front home features an open floor plan enabling you to interact with others easily. It has free stateside calls, central air, three sitting areas, all new kitchen appliances, bottled water quality water...
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    West End, Cayman Brac KY2 2001
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern condo with Amazing Caribbean Views! You will see the cruise ships arrive into port each morning from the privacy of your second floor lanai. There are 2 bedrooms and 2 bathroom, which are modern and new. The open kitchen has stainless appliance with sleek Granite counter tops. There is a...
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    Seven Mile Beach, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tiki House Grand Cayman, Seven Mile Beach Area1 / 102
    (24)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2017
    If I could give the Tiki House a higher rating, I would! The location, for starters, is ideal. Being a 2 minute walk from the famous Seven Mile Beach alleviated the stress of...
    Reviewed March 4, 2017
    On booking a dive/vacation trip for 6 people to the Caymans, we decided to try VRBO instead of having to get three separate hotel rooms. We located the Tiki House, read the...
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    About this property
    Beautiful private residence. Tiki House is set behind a coral wall, with wonderful garden patio shaded by a bougainvillea trellis. Great ocean views and just steps to Seven Mile Beach's sandy, palm shaded public beach. Famous snorkeling at Cemetery Reef is close by as are great local restaurants,...
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    West Bay, Grand Cayman KY 1
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Condo on 7 Mile Beach - Great Location - Ground Fl1 / 14
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 19, 2017
    We loved staying at the condo for our trip! Very spacious, clean, and comfortable. The staff was super nice and very helpful! Highly recommend
    Reviewed March 19, 2016
    This apartment met all of our expectations. Located more towards the south end of Seven Mile Beach, it provided quick access to eating establishments, grocery stores, and the...
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    About this property
    Ideally located condo on the renowned 7 mile beach. This spacious condo, on the ground floor, has 2 bedrooms, and 2 full bathrooms, with a sofa bed in the living room. This air-conditioned unit, with fitted wardrobes, Wi-Fi, safety deposit box, fully equipped kitchen, TV and DVD player, ceiling...
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    Seven Mile Beach, Grand Cayman KY1 1204
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Featherstone's House of the Rising Sun1 / 5
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2015
    i have come to the caymans for quite some time and find this place my favorite. charming. quiet. the owner helpful with any questions concerns or needs. a definite return for...
    Reviewed April 24, 2015
    Featherstone has a two story cottage, where we stayed, that sits behind the owner's two story main house. It is very private and beautifully decorated by the interior...
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    About this property
    Romantic and beautiful cottage located on the most beautiful totally private beach on the island. Professionally decorated with a second story balcony off the upstairs bedroom overlooking Paradise. In back is a private garden under the almond trees with a hot tub. The beach is 1 1/2 acres of...
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    Cayman Brac, Cayman Islands KY2 2201
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Castaway by the Sea - Lodge1 / 11
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2017
    Thom and Susan's little paradise is perfect for R&R. This "tiny" home is completely efficient and equipped.. just bring your swim suit and snorkel !! The environment...
    Reviewed April 28, 2016
    We stayed at Castaway lodge for 6 nights in March. The place is owned by a wonderful couple called Thom and Susan who are down the road if you need anything. The cottage is...
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    About this property
    If you enjoy being on the beach, Castaway Lodge by the Sea is a cleverly designed and thoughtfully appointed cottage set back 125 feet from the water’s edge. It is a charming, immaculate and well equipped, air conditioned studio style bungalow situated on a half acre, with your own private beach....
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    Bodden Town, Grand Cayman KY1 1601
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grand Cayman Sea Lodge Oceanfront on North Side1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    North Side, Grand Cayman KY1 1109
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Reef Resort - Grand Cayman: 1-BR, Sleeps 4,1 / 37
    (8)Very good
    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 April 18, 2018
    Booked and payed for a 2 week vacation at the wyndam, at the end of the first week we were told we had to move due to booking error, we had to move to a different resort, we...
    Reviewed January 30, 2018
    Loved the condo - view just stunning. Condo had everything we needed and the beach was awesome . Very windy for most of our stay so made it quite noisy during the night...
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your own piece of paradise… COCOPLUM#1 Enjoy the look and feel of a casual Caribbean family villa with privacy and plenty of open space. Whether you are considering a couples get away or family adventure, Cocoplum is your perfect island escape. Experience the tranquility of this ground...
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    Location Information
    Seven Mile Beach, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kaibo “7UP” is a beautifully furnished and outfitted second floor condo at the Kaibo Yacht Club Phase 2 in tranquil Cayman Kai, on the north side of Grand Cayman Island This 2 bedroom, 2 bathroom condo is furnished with warm wood furniture in relaxing colors The master bedroom features a king size...
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    Rum Point, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront 2 Bedroom Condo #33 at Serene&Exquisite Retreat at Rum Point1 / 30
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Balcony
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2018
    This place is truly wonderful and the location is perfect! We stayed at several Airbnb places but this one by far is the best. The condo was clean and very comfortable. The beds...
    Reviewed April 8, 2018
    This place is awesome - very quiet, safe and right on the beach. It is situated on a leeward side of the complex, so it is sheltered from the winds and any construction noise...
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    About this property
    Located directly on the beach at the popular Retreat Resort right in the heart of Rum Point in the North Shore. This non-smoking two bedroom/two and a half bathroom condo is beautifully updated with a fully equipped new kitchen, vaulted ceilings (with fans) and with high quality furniture...
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    Location Information
    Rum Point, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Great Location & Value! 7mile Beach Condo next to *NEW*  Margaritaville Resort1 / 30
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Children's Pool
    • Hot Tub
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 2017
    Livia was a brilliant host.I cannot recommend her more. No matter what we needed she was on it like a bonnet. Apartment has everything you need and if you lack anything she...
    Reviewed July 24, 2017
    The condo, swimming pools, landscaping, and beach are beautiful and well maintained. There are sailboats, kayaks, sea food, paddle boards and other equipment available less than...
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    About this property
    Beachfront condominiums, right next to the New Margaritaville Resort. You do not need to cross the road to get to the beach as the condos are on the beach side. The unit is on the ground floor and has a garden view. It is not facing the beach however a 2 minute walk to the beach and NO HASSLE of...
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    Location Information
    Seven Mile Beach, Grand Cayman KY1 9006
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Wyndham Reef Resort: Studio, Sleeps 2, with Kitchenette1 / 39
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 20, 2018
    The view is worth the trip. Awake daily and set on the veranda and enjoy the Caribbean sea. The room is functional and the bed was super comfortable. The only negative I can...
    Reviewed January 1, 2018
    The price was really competitive against others in the area. Staying during the busy season is really expensive and we were glad to find this place which offered a kitchenette...
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    About this property
    Wyndham Reef Resort: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Saturdays check in only. Studio Beach Suite Our Grand Cayman Studio suite is beachfront with an area of approximately 450 square feet, including its own balcony. Studio suits two, with a king size bed overlooking the...
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    Location Information
    East End, Grand Cayman KY1 1801
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kai Time Island House, Cayman Kai/Rum Point1 / 37
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 28, 2017
    Our ten day stay at Kai Time Island House (#14) could not have been better. Kudos to the owners who have made this place so welcoming - no details have been overlooked. This...
    Reviewed June 8, 2017
    We wanted a vacation that included quiet time yet had the amenities close by. We had a great time snorkeling at Rum Point, handling the starfish, and time at Kaibo. We also to...
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    About this property
    Cayman Kai Vacations specializes in offering the 'Island Houses of Cayman Kai' Tranquil Fruition, Calico Kai, Barefoot Lagoon, Summer Breeze, Toto Kai, Kai Time, Dream Kai, Casa Kai, Kai Kotch, Kai-lypso, Mango Kai, which are located in the exclusive Cayman Kai/Rum Point area on Grand Cayman,...
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    Location Information
    Rum Point, Grand Cayman GRAND CAYMAN CAYMAN ISLANDS
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Children's Pool
    • Hot Tub
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Reef Resort - Grand Cayman: Studio, Sleeps 2, with Kitchenette. Fixed week - 7 nights, Saturdays check in only. Two Bedroom Master Suite The resort's Grand Cayman Two Bedroom Master Suite, which comfortably sleep six people, is beachfront with an area of approximately 1,350 square feet, plus...
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    Location Information
    East End, Grand Cayman 55555
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayman Islands Kaibo Yacht Club Condo - Rum Point1 / 31
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2018
    We have so enjoyed our stay here. We have absolutely lived in the lovely screened in area of the condo. The island is incredibly beautiful and welcoming. We cannot say enough...
    Reviewed January 25, 2017
    I stayed at this Rum Point condo for one week with my family. I must say that my trip was near perfect. The condo itself was "fully loaded" which made our stay very...
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    About this property
    Kaibo is what you have dreamed about when you think about an island getaway. It's fun, exciting, romantic, peacful and more all wrapped into one. We have a beautiful beach, a view that looks like a postcard and all the amenities you could want or need for a tropical paradise. Come visit us at Kaibo...
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    Location Information
    Rum Point, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Morning Glory1 / 24
    (7)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 28, 2018
    My wife and I stayed here as guests of a wedding party. I was first impressed at the architecture and construction of this villa. From lighting to sound system it is quite the...
    Reviewed January 10, 2018
    This magnificent house is close to spotts beach, but even though it would only be about a 5 minute walk, there is really no where to walk along the roadside. The view is...
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    About this property
    Morning Glory is truly one of the most elegant residential estates on the south coast of Grand Cayman. This state-of-the art house features 5 bedrooms and 5.5 bathrooms in the main house, and a spacious 2 bed/1 bath apartment above the garage, that all together comfortably accommodates a total...
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    Location Information
    Savannah, Grand Cayman KY1 1000
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our property is a duplex of 3 bedrooms 2 bathrooms each unit. It has a site dimension of 10,215 sq ft. This huge space outdoors makes the Apartment suitable for children (above age 2) who like to play outdoors. The floor area is approximately 2,800 sq ft each unit. The master bedroom has a...
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    Location Information
    George Town, Grand Cayman KY11007
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rum Haven1 / 16
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 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 January 2, 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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    Shellen1 / 27
    (12)Very good
    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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    Location Information
    East End, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    On The Bay #1041 / 18
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2018
    The condo was very well equipped and spotlessly clean. Very relaxing weekend would highly recommend.
    Reviewed January 10, 2018
    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...
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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...
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    Old Man Bay, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Paradise Home # 4 Green Summer Discount 10-20% Off1 / 37
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 22, 2017
    My wife, daughter and myself reserved this 3 bedroom, 3 bath for a weeks vacation just before Christmas. We absolutely loved the first class accomodations. It was nice for all...
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    About this property
    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 City, Rum Point and...
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    Location Information
    Rum Point, Grand Cayman KY1 1206
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Little Cayman Escape1 / 16
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
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    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 2018
    The place met or exceeded every expectation. Secluded, pristine, tranquil private, comfortable. Escort to and from airport. The ultimate in stress management. Managment was a...
    Reviewed October 22, 2017
    Accommodations perfect! View beautiful! Nighttime stars amazing! Snorkeling easy and interesting. We had a fine time!
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    About this property
    Little Cayman Escape is a unique, 3-bedroom, 2-bath (sleeps 9) villa on the beach in charismatic Little Cayman—the smallest and least populated of the Cayman Islands. With its circular architecture (including wraparound terrace), secluded location, and big windows overlooking the Caribbean, a stay...
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    South Town, Little Cayman KY1 1202
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Ocean's Edge Grand Cayman Condo1 / 34
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2016
    First the good part. The condo has a great view. The lanai is great, though it would have been nice to have a couch of some sort. I loved the quiet, there was maybe 1 other...
    Reviewed May 27, 2015
    Not only was this condo exactly as described, it exceeded adequate description. You are right on the ocean's edge; I hardly have seen anybody here except occasional visits by...
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    About this property
    Aqua blue ocean views from every window describe the Ocean's Edge. Newly built and located in the exclusive Rum Pointe area of Grand Cayman (the quiet, unspoiled side of Cayman)it is part of a small 10 unit complex with private beach and pool. Located in the exclusive Rum Point, Cayman Kai area...
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    Location Information
    North Side, Grand Cayman XXXXX
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Condo, 2 Bedrooms + Convertible beds 2 Baths, (Sleeps 4-6) ASK ABOUT SPECIAL RATES JULY 14-19 LOCATION IS EVERYTHING! NO STAIRS GROUND FLOOR UNIT Centrally located you will find our spacious 2/BR, 2/Bath ground floor villa situated in one of the finest sections of Seven Mile Beach at Villas of...
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    Seven Mile Beach, Grand Cayman BWI
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Magic1 / 16
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
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    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2016
    We recently vacationed at Sea Magic with our dear friends. Between the two families, there were 3 teenagers, and this was the perfect house for us. There are actually 2 and a...
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    About this property
    This recently renovated 2 bedroom villa has spared no detail. With 2 bedrooms and 2 bathrooms, it is perfect for a couple of friends or a small family who want a Caribbean vacation home that has the quaint character of an islandy cottage - with the luxurious design details of an upscale villa....
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    North Side, Grand Cayman KY1 1202
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt1 / 48
    (30)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    Reviewed March 1, 2015
    Island House 17 was a perfect rental property for our vacation. My boyfriend and I traveled with another couple. The house is located in a peaceful community on a beautiful cove...
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    About this property
    Looking for a peaceful, relaxing Caribbean vacation experience in a beautiful beach-front spot that's easy to reach? Come find your slice of paradise at Kai Kotch.  It's a charming 2-bedroom home on a secluded sandy beach in the prime vacation location of the Rum Point / Cayman Kai area of Grand...
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    Location Information
    North Side, Grand Cayman KY1 1105
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Pools #121 / 11
    (10)Excellent
    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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    Villa Bellagio1 / 29
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 26, 2018
    We rented this beautiful home for a family celebration of two "special" birthdays, Father's days for two, and to have an annual epic vacation. This amazing home was...
    Reviewed February 8, 2018
    The house was very comfortable for all 10 of us that stayed, very clean, had enough amenities to last the entire week we were there. We were not able to swim in the bay due to...
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    About this property
    Nestled amongst whispering palms on The Cove in the popular Cayman Kai area on the north coast is a comfortable family home that welcomes all! Arranged on two floors this is the perfect ‘home from home’. With 5 bedrooms and 5 bathrooms this beach house makes for the perfect family get-together...
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    North Side, Grand Cayman KY1 1000
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Kaibo Yacht Club #20B1 / 16
    (15)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 27, 2018
    Lovely condo at Kaibo Yacht Club. Perfect for two couples. Amazing view from the balcony and steps from the beach. Great pool and hot tub and well kept grounds. Water a little...
    Reviewed November 6, 2017
    Stayed here for 5 days and loved every minute of it . We normally stay on SMB but always wanted to try a few days on the north side. Althgouh it was low season and a couple of...
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    About this property
    A popular boater’s destination and condo complex, Kaibo Yacht Club in Cayman Kai gathers locals and visitors alike, who dock at the Club to grab beachside BBQ, a tropical cocktail, or a gourmet meal. All of these options are available to you, of course—right outside your door at this Kaibo...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Soleil d'Or Luxury Beach Cottage, Private Pool1 / 14
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 14, 2016
    I recently spent a week in the Le Soliel d'Or cottage with my husband and two-year-old daughter and can not wait to return. It was the perfect place to spend time together as a...
    Reviewed December 8, 2015
    I just returned from a stay in the "Cottage" at Le Soleil d'Or. I feel like I'm now returning from heaven. What a unique and fabulous experience. I was able to tour the...
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    About this property
    Tranquil and secluded. The single-story Beach Cottage retreat is the perfect location for a honeymoon, small family or a relaxing, romantic escape. This oceanfront getaway sleeps two to four and includes your own private pool and beach. Le Soleil d'Or is home to its very own organic 20-acre...
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    Location Information
    Cayman Brac, Cayman Islands KY2 2000
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A seafront balcony at this 2-bedroom, 2-bath condo unit waits for you to come out with a morning coffee or an evening glass of wine to watch gentle waves lap the shore. The indoor space just received a facelift, so it’s just as striking as its surroundings in historic Bodden Town on Grand Cayman....
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    Bodden Town, Grand Cayman KY1 1000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rum Sands1 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2016
    This was a wonderful spot to stay if you're looking for something away for the crowds and plan on doing your own cooking. The home is surrounded by water and is a perfect getaway.
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    About this property
    Upgrades to this charming one-bedroom, one-bath Rum Sands, located on a quiet cove in Cayman Kai, create both a romantic luxury cottage and a 100% authentic Caymanian escape. Find stainless steel appliances, coastal-chic décor, Caribbean cross-breezes, lots of sunshine and a luxurious king-sized...
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    North Side, Grand Cayman KY1 1202
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the newly renovated ground floor, 2 bedroom unit at George Town Villas! Inside you will find big, sea-view windows where you see the beauty of the Caribbean waters. The open concept kitchen, dining and living area makes for the perfect place to gather after a sun filled day. The open...
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    George Town, Grand Cayman KY1 1002
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you on the hunt for an away-from-it-all retreat, where you can take a stroll on a pristine Caribbean beach all to yourself? Look no further than this second-floor, two-bedroom gem of a condo, Villas Pappagallo #1B, on the quiet, never-crowded northwest shores of Barkers Beach in West Bay....
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    West Bay, Grand Cayman KY1 1000
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Villas of the Galleon  7 Mile Beach, Ground Floor!1 / 44
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
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    • Air Conditioning
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2017
    This condo is situated right between the Ritz and the Westin. It is the perfect location. You can rent kayaks, boats, paddle boards, and wave runners right in front of the...
    Reviewed December 9, 2015
    This was our second stay at this condo. It was newly painted this time and very clean, as was the case the previous time we stayed here. It's in a great location on Seven Mile...
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    About this property
    ASK ABOUT OUR SPECIAL WiFi access BIG screen TV You will find this spacious 2/BR, 2/Bath ground floor villa situated in one of the finest sections of Seven Mile Beach at Villas of the Galleon, where the beach is only about 100 ft from our porch. Within a short 1/4 mile walk is a modern...
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    Location Information
    Seven Mile Beach, Grand Cayman BWI
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kailypso1 / 24
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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 will love this 3-bedroom, 2-bath beach house situated on a secluded cove (Bio Bay), in a residential area in Cayman Kai, strolling distance from the Rum Point Beach Bar and Restaurant It’s easy to see what makes Kailypso such a popular beach house for group getaways. It...
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    Location Information
    North Side, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Villa Esprit1 / 23
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 a fully equipped modern kitchen with new appliances,...
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    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Washer
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 City, Rum Point and...
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    Rum Point, Grand Cayman KY1 1206
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Moon Bay #31 is a wonderful complex located on the majestic south shore. Just a few (barefoot) steps from the condo will lead you to the beach. Snorkeling the reef is a favourite activity here—it is teeming with vibrant and fascinating sea life. At the right time of year the beach at Moon Bay is a...
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    Location Information
    Bodden Town, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Terrace
    • Ocean Views
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private, spacious 2 bedroom beachfront condo. Great for small families or couples retreats. This spacious beachfront condo is spread over two floors with all of the amenities that one could need. A large corner patio, two full bathrooms and a fully equipped kitchen will make you feel at home upon...
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    Location Information
    Bodden Town, Grand Cayman KY1
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Paradise Home # 1 Cream - Summer Discount 10-20% Off1 / 8
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2017
    This newish house is very nice. However, it's easy to see that the upkeep hasn't been as frequent as it needs to be--but it was comfortable none-the-less. The house was always...
    Reviewed February 18, 2017
    Great location for families, friends, right on the beach which is great for snorkeling and costal walks, there are sea urchins so proper footwear needed. Saw plenty of fish...
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    About this property
    Summer Discount 10-20% Off Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray City, Rum...
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    Location Information
    North Side, Grand Cayman KY1206
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Pools #101 / 14
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We stayed in this same unit in January 2018 and had a fantastic time so we brought our brother and sister in law to join us in August. The condo had be painted and freshened up...
    Reviewed 2 weeks ago
    We just stayed (July 9 - 19) at the Pool #10 and had an amazing time!! The property was updated and looked beautiful. It had all that we needed - towels, washing /dryer...
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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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    Kirk Kove1 / 15
    (8)Very good
    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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    White Sands #161 / 16
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Grill
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 17, 2018
    Lovely beach, water, and shade trees nicely separated from the crowds at mid 7 mile beach. Condo shows some age but manager, Margie very responsive, pleasant and helpful. This...
    Reviewed May 5, 2016
    My wife, 20 something daughter and I stayed at White Sands # 16 for a long weekend. Though it was somewhat a spur of the moment trip Cayman Villas was, as always, prompt and...
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    About this property
    Escape the hotel crowds and tuck into a quiet beachfront condo resort that has everything you need and nothing you don’t. This two-bedroom, two-bath retreat is located on Seven Mile Beach’s slow-paced northern end. Here, you’re just a short shoreline stroll from some of Seven Mile’s best...
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    Location Information
    West Bay, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Plantation Village 411 / 23
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 2018
    The home was in great condition and spacious for 4 people. Beds were very comfortable and there were plenty of kichen tools. The pools and areas were clean and close to...
    Reviewed November 10, 2016
    The place was very clean, it had a few issues with the water drainning very slow in the tub but that was it.
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    About this property
    SPECIAL ALERT *** 20% OFF THE NIGHTLY RATE FOR DATES IN JUNE, JULY AND AUGUST 2018- for new bookings only. Plantation Village is perfectly situated on the southern end of Seven Mile Beach. This 2 bedroom, 2 bathroom unit is positioned in the centre of the complex on the ground floor with a...
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    Location Information
    Seven Mile Beach, Grand Cayman KY1 1204
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Paradise Home # 3 Blue - Summer Discount 10-20% Off1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2017
    Ocean paradise is awesome what u see in the pictures is what u get u only need food and drinks the place is as advertised 5 stars the view is amazing the one minor complaint...
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    About this property
    Summer Discount 10-20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous...
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    Location Information
    Rum Point, Grand Cayman KY1 1206
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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