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Holiday Rentals with Pools in North Side

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    €280 Average
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    Travellers to North Side are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    13 Matching Rentals in North SideView all 19 rentals
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    Coral Loft - Casual Living With A Luxurious Twist1 / 24
    (15)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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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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    No Big Ting - Luxury Beach Villa with a Pool!1 / 34
    (26)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    'A Mid-Winter Night's Dream' Grand Cayman Oceanfront, Quiet, Secluded, Rum Point1 / 21
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    We had such a great time at Dams place! Everything you could need and great comfort. The ocean is literally 60 feet from the pool. Such a quiet relaxing place. I would recommend...
    Reviewed 31 December 2016
    Our family went to Grand Cayman over Christmas this year. Back in February, 2016, we had booked a condo on the East end of the island. I decided to shoot them a quick email 3...
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    About this property
    Located in the quiet and secluded Cayman Kai / Rum Point area of Grand Cayman, 'A Mid-Winter Night's Dream' is an ideal place for a tropical getaway. Situated on the ground floor, directly overlooking the ocean, we have great views of the Caribbean from every window. The screened-in lanai is a...
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    Location Information
    North Side, Grand Cayman 00000
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kai Kotch, #17 Island Houses of Cayman Kai, Rum Pt1 / 96
    (30)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    In addition to all the activities available, the covered, screened-in lanai was great to to relax on without being "bugged." Also, awesome local owners.
    Reviewed 1 March 2015
    Island House 17 was a perfect rental property for our vacation. My boyfriend and I traveled with another couple. The house is located in a peaceful community on a beautiful cove...
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    About this property
    Looking for a peaceful, relaxing Caribbean vacation experience in a beautiful beach-front spot that's easy to reach? Come find your slice of paradise at Kai Kotch.  It's a charming 2-bedroom home on a secluded sandy beach in the prime vacation location of the Rum Point / Cayman Kai area of Grand...
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    Location Information
    North Side, Grand Cayman KY1 1105
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean Oasis - Private Beachfront Villa With POOL1 / 49
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2016
    We love the north side, and enjoyed this house. The pool is phenomenal and well-situated, both for the view and to avoid getting overheated by afternoon sun. The house was a...
    Reviewed 5 August 2016
    The Ocean Oasis home is located on the quieter, East end of Grand Cayman, and we truly felt like we had our own island getaway. The house and grounds are very spacious and...
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    About this property
    This private residence has opened its doors to become the ultimate vacation rental. The brand new pool is complete and includes a built in bench the entire length of the pool, it is perfect for soaking in the view. Come enjoy all of the comforts of home with the luxury of panoramic ocean views....
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    Location Information
    North Side, Grand Cayman KY1 9006
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beachfront,Step from Your Porch Onto the Sand1 / 60
    (64)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 30 July 2017
    This condo is really nice. All the details is a sure sign of proud owners. We enjoyed our stay here.
    Reviewed 29 July 2017
    This condo was completely equipped with everything you could need for a wonderful stay. The owners have really done a wonderful job providing everything needed to make it feel...
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    About this property
    Location: Cayman Kai, North Shore, Grand Cayman, Cayman Islands, Caribbean (Beachfront, Cayman Kai, Kaibo Yacht Club, Rum Point area) Accommodations: Condominium, 2/2, sleeps 6, Cayman Kai Welcome to Blue S'Kai, our white sand beach getaway condo is new to the rental market in beautiful,...
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    Location Information
    North Side, Grand Cayman KY1 1701
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Paradise Home # 4 Green - Fall 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
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Paradise Home # 5 Yellow - Fall 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
    Fall Discount 20% Off Ocean Paradise is perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat. Ocean Paradise offers luxury and relaxation in world-class vacation accommodations yet is conveniently located near world-famous Stingray...
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    Location Information
    North Side, Grand Cayman KY1 1006
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Flip Flop Kai1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2017
    This was our first trip to the Cayman Island. Our stay at Flip Flop Kai was absolutely perfect. The home was actually better in person then it looked online. We truly enjoyed...
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    About this property
    Welcome to Flip Flop Kai! This beautiful 3 bedroom, 3 bathroom and den villa is nestled on a sandy beach overlooking the bioluminescent Cove in Cayman Kai. This home has gorgeous views from almost every room and a wonderful covered beach side veranda where you can listen to the gentle lapping of...
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    Location Information
    North Side, Grand Cayman KY1 1000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Caymanease An Oceanfront Home on a Private Beach with a Pool and Kayaks1 / 33
    (36)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 6 August 2017
    My husband and I booked the Caymanese for our family to celebrate our oldest daughter's college graduation. We enjoyed every minute of our stay! The Caymanese is a beautiful...
    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...
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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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    6 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The immensely popular Coco Kai Villa is now available directly from the owner. This property is situated in the quiet, pristine area of Cayman Kai. Our home also has an in-ground pool and sits on the beautiful beaches of the Caribbean. This is a very private, exclusive part of beautiful Grand...
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    Location Information
    North Side, Grand Cayman KY1
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 15
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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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