We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in North Side, Cayman Islands

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €327 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to North Side are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 24
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 34
    5 of 5 bubbles (22) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 24
    5 of 5 bubbles (13) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 48
    5 of 5 bubbles (30) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • 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 KY1 1105
    5 of 5 bubbles 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 bubbles 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...
    See all reviews
    1 / 20
    5 of 5 bubbles (58) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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,... View all property information
    Location Information
    North Side, Grand Cayman KY1 1701
    5 of 5 bubbles Reviewed 2 days ago
    First time on the Island , and we lucked out ! Best location and condo! Before we even left home the owners provided us with so much information, directions from the airport...
    5 of 5 bubbles Reviewed 13 July 2016
    Awesome!!!! The owner was very helpful and informative. The condo was very clean with all the amenities you could need and more!!! Will definitely recommend to friends and...
    See all reviews
    1 / 35
    4.5 of 5 bubbles (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    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 XXXXX
    3 of 5 bubbles Reviewed 12 November 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...
    5 of 5 bubbles 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...
    See all reviews
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Parking
    • Private Outdoor...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman KY1 1000
    1 / 16
    5 of 5 bubbles (34) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    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 KY1 1006
    4 of 5 bubbles Reviewed 16 November 2016
    We had family visiting so decided to rent a cottage on the North Side for the bank holiday weekend. We had house no. 2 which is at the rear. I would recommend staying in one of...
    5 of 5 bubbles Reviewed 26 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...
    See all reviews
    1 / 34
    5 of 5 bubbles (33) Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    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 KY1 1107
    5 of 5 bubbles Reviewed 2 weeks ago
    This house has great amenities, comfortable beds, very well-equipped, and so well decorated! The house has a pool and its own private beach; the view is gorgeous! This is one of...
    5 of 5 bubbles Reviewed 2 weeks ago
    I spent a week with friends celebrating a birthday at Caymanease. It was wonderful! The house is well stocked, beautifully decorated, spacious, and has a private beach. We felt...
    See all reviews
    1 / 28
    5 of 5 bubbles (35) Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    North Side, Grand Cayman KY1 1702
    5 of 5 bubbles 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 have...
    5 of 5 bubbles Reviewed 7 July 2016
    What a wonderful villa! Spacious for our family of 14, well stocked, gorgeous views, helpful and friendly owner and service people, The gazebo was perfect for coffee at...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 45
    5 of 5 bubbles (9) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    North Side, Grand Cayman KY1 9006
    4 of 5 bubbles 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...
    5 of 5 bubbles 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...
    See all reviews
    1 / 7
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    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 KY 1006
    5 of 5 bubbles 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...
    5 of 5 bubbles 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...
    See all reviews
    1 / 20
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    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 KY11007
    5 of 5 bubbles 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 is...
    5 of 5 bubbles 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 out...
    See all reviews