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Holiday Rentals with Pools in North Side, Cayman Islands

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    Travellers to North Side are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    1 / 20
    5 of 5 stars (56) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 45
    5 of 5 stars (8) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 34
    5 of 5 stars (21) 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...
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 1 week ago
    WOW! From our first impression to our departing day! What an amazing villa with wonderful owners. Its always hard searching for the perfect place to call home while you are on...
    5 of 5 stars Reviewed 30 July 2016
    I spent a week at No Big Ting with my wife, three daughters and aunt and uncle. Walking up the fron steps and into the house on day one our five year old twins decided this was...
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    1 / 48
    5 of 5 stars (30) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Washer
    • Satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 1 May 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    5 of 5 stars Reviewed 2 March 2015
    Island House 17 was a perfect rental property for our vacation. My boyfriend and I traveled with another couple. The house is located in a peaceful community on a beautiful cove...
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    1 / 24
    5 of 5 stars (13) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Washer
    • Waterfront
    • Ocean Views
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 23 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...
    5 of 5 stars Reviewed 19 August 2015
    Coral Loft was everything we expected and more. The place was excellent and the location was what we were looking for, very private and relaxing. Our 2 grandchildren, ages 4 and...
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    1 / 34
    5 of 5 stars (31) 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...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Caymanease is a private, oceanfront villa 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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 18 July 2015
    Let me start by saying, I am writing this while sitting at Caymanease, looking at the sea. Everything you read in the previous reviews is accurate. Pictures cannot do the house...
    5 of 5 stars Reviewed 1 May 2015
    This was our 3rd trip to Caymanease and we had another awesome trip. My husband takes the kayaks out for some early morning fishing. We all love snorkeling the reef just off the...
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    1 / 35
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool...
    • Satellite TV
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.<BR><BR><BR>Located in the exclusive Rum Point, Cayman... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 27 May 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...
    5 of 5 stars Reviewed 16 December 2014
    The condo was perfect. Owners gave directions there and list of cruise ships coming into town so we could pick a day to go into town with less congestion. Everything is provided...
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    1 / 16
    5 of 5 stars (33) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 27 June 2016
    Booked two house for a group of 11 - ages 12 to 79. Very well appointed, comfortable and location cannot be beat, just beautiful. The food and sundries on the island are 2 to 4...
    4 of 5 stars Reviewed 19 May 2016
    We stayed in the yellow house #5. And I think it's really the absolute best house there. Its the most private. We were told by the cleaners that people often think they are...
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    1 / 7
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 6 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...
    5 of 5 stars Reviewed 15 March 2015
    Best Vacation Spot Ever My 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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    1 / 20
    5 of 5 stars (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...
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman
    5 of 5 stars Reviewed 25 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 is...
    5 of 5 stars Reviewed 13 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 out...
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