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North Side Holiday Vacation with Pools

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    $468 Average
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    Travellers to North Side are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    11 Matching Rentals in North SideView all 17 rentals
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    Ocean Pearl Beachfront Townhome Vacation Rental1 / 27
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 45
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    Beachfront,Step from Your Porch Onto the Sand1 / 20
    (62)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2017
    This condo was well maintained and loved the decor. The complex has a pool and a hot tub - great for relaxing after a day of play. The area in Kaibo was peaceful and beautiful...
    Reviewed 23 February 2017
    A perfect condo. It is equipped as well as your own home. Love the fact that the beach and small pool is right outside the door.
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    About this property
    Location: Cayman Kai, North Shore, Grand Cayman, Cayman Islands, Caribbean (Beachfront, Cayman Kai, Kaibo Yacht Club, Rum Point area) Accommodations: Condominium, 2/2, sleeps 6, Cayman Kai Welcome to Blue S'Kai, our white sand beach getaway condo is new to the rental market in beautiful,...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Paradise Home # 5 Yellow - Summer Discount 20% Off1 / 16
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    We hosted our wedding at Ocean Paradise this past weekend and could not have asked for a better wedding venue! We rented out all 5 homes and our wedding party stayed in them for...
    Reviewed 9 April 2017
    Amazing find with a great location. We stayed in one of the beachfront homes away from the crowds in GeorgeTown. If you like peace and serene environment, you dont need to look...
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    About this property
    Summer Discount 10% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY1 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coral Loft - Casual Living With A Luxurious Twist1 / 24
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Waterfront
    • Ocean Views
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    WOW is all I could think when I walked in and saw the wall of windows and the perfect view to the ocean. The home was clean and laid out so there were little gathering spaces...
    Reviewed 22 August 2016
    Coral Loft was everything we were promised and more. The pictures do not come close to the breathtaking reality as one enters the house. This is a very clean, spacious, and...
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    About this property
    This four bedroom beach house underwent a massive renovation in 2013, including the addition of a pool. Coral Loft is on the ocean in the Cayman Kai neighbourhood, a mere mile from the famous Rum Point Beach. The home sits atop a high ridge, offering panoramic views of the ocean as well as the...
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    No Big Ting - Luxury Beach Villa with a Pool!1 / 34
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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.
    Reviewed 27 December 2016
    Amazing view, wonderful large screened in porch, pool and a house that is very comfortable and stocked with everything! Bikes, snorkel gear, pool toys, every kitchen dish and...
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    About this property
    This renovated three bedroom home in the Rum Point / Cayman Kai area of Grand Cayman has every amenity you could want and now includes a solar heated pool. It has all the luxuries of your home but sits on over a half acre of beach and the back door is steps away from the ocean. The cooling sea...
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Paradise Home # 4 Green - Summer Discount 20% Off1 / 7
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2015
    Lovely place. Really enjoyed our time here, felt like we discovered the best the island has to offer. Owners are very helpful. Cleaning people do a fantastic job! The kitchen...
    Reviewed 15 March 2015
    Best Vacation Spot EverMy wife and I took our family (son, daughter, their spouses and our 15 month old granddaughter) to Grand Cayman to escape the brutal Ohio winter in...
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    About this property
    Summer Discount 10% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6BR-Far Tortuga Oceanfront Villa, rents as 4,5,6BR1 / 56
    (36)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2017
    Fantastic house, beautiful location, had all amenities for a perfect holiday. Fully equipped, air conditioning, two fridges, washing machine, loads of towels, very comfortable...
    Reviewed 6 October 2016
    I can't say enough about Far Tortuga. From the beginning working with Vince to finally arriving, it was all so fantastic! The home was exactly as I expected. The bathrooms...
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    About this property
    Book directly from the owner and avoid extra fees and charges. Situated in one of the best areas for snorkeling, this luxury home has a breathtaking view of the beach, sparkling warm ocean, and foamy reef. Each room is designed to catch the fresh sea breezes, give an air of spaciousness with high...
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    Location Information
    North Side, Grand Cayman KY1 1702
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Caymanease An Oceanfront Home on a Private Beach with a Pool and Kayaks1 / 33
    (35)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2017
    Fabulous beach home that the owners obviously take pride in. And I emphasize home - not just your standard rental. - It is immaculately clean, beautifully decorated, and...
    Reviewed 19 March 2017
    We were a group of seven who had the pleasure of staying at Caymanease over the Christmas holidays. The house easily accommodated our group and we never felt crowded or on top...
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    About this property
    Caymanease is a private, oceanfront home with a pool sitting on a secluded, private sandy beach located in the North Side of Grand Cayman. This villa sleeps 8 and offers 3 bedrooms and 3 and 1/2 baths, and enclosed outdoor shower, an oceanfront pool, kayaks and all the amenities you need to have a...
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    Location Information
    North Side, Grand Cayman KY1 1107
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    Beachfront Winter Getaway at Resplendent Kaibo1 / 20
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Waterfront
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2014
    We loved stay. This is our 7th trip to Cayman and we have never stayed in the same place twice. Next year we will be staying here again and many years to come. The location...
    Reviewed 12 April 2014
    My husband and I and our two young boys (3 & 5) stayed at this condo for almost a week. It was perfect and I'm so glad we booked this one. The condo itself was nicely laid...
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    About this property
    Located at the Kaibo Yacht Club Phase 2 in Grand Cayman's exclusive Cayman Kai area, this is a 2 bedroom/2 bathroom condo, recently refurbished and fully equipped. Sleeps up to 6 persons, with king size bed in master bedroom, full size bed in second bedroom and has a queen-sized sofa bed in living...
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    Location Information
    North Side, Grand Cayman KY11007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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