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Vacation Rentals with Pools in North Side and nearby

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    $755
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    1 / 24
    5 of 5 stars (10) Excellent
    North Side
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    $220
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    1 / 13
    5 of 5 stars (11) Excellent
    North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    North Side
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    $648
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    1 / 34
    5 of 5 stars (30) Excellent
    North Side
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (30) Make Enquiry
    Amenities & Details
    • Internet Access
    • Swingset
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Caymanease is a private, oceanfront villa with a pool sitting on a secluded 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 relaxing and... View all property information
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    Location Information
    North Side, Grand Cayman KY1 1107
    5 of 5 stars Reviewed 30 April 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...
    5 of 5 stars Reviewed 11 August 2014
    We stayed at Caymanease for a week in mid June 2014. What an amazing place on a wonderful island. The home is perfectly decorated, stocked and in the perfect location! The...
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    $897
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    1 / 28
    5 of 5 stars (30) Excellent
    North Side
    6 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Reviews (30) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Water Views
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    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 cathedral ceilings, and enjoy the ever changing aquamarines of... View all property information
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    North Side, Grand Cayman KY1 1702
    5 of 5 stars Reviewed 3 June 2015
    Our party of six included me and my husband, our two adult children, my 83 year old father and a girlfriend. We wanted a house where we could relax, enjoy each other's company...
    5 of 5 stars Reviewed 21 May 2015
    My group of 8 girlfriends have been traveling together for 19 years, and have stayed in many great villas in the Caribbean. Far Tortuga has got to be one of the best. Vince was...
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    1 / 14
    5 of 5 stars (4) Excellent
    North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Waterfront
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool...
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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, 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
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    North Side, Grand Cayman KY11007
    5 of 5 stars 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 stars 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...
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    $326
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    1 / 7
    4.5 of 5 stars (3) Very good
    North Side
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Waterfront
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    North Side, Grand Cayman KY 1006
    5 of 5 stars 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 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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    $1,252
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    1 / 13
    4.5 of 5 stars (3) Very good
    North Side
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Ecstasea is located on the Northside of the island just about 1 mile east of the Rum Point Club. The 5BR stately villa is now painted a sage green with white trim and enjoys a wonderful beach. The main living area is octagonally designed for maximum views. The pool & beach are very private.... View all property information
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    Location Information
    North Side, Grand Cayman 00000
    5 of 5 stars Reviewed 18 August 2014
    5BR Ecstasea was an excellent choice for our ten days on the North side this past March, away from the hustle and bustle of Georgetown. Location, water quality, beach access and...
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    The following rentals are within 10 kilometres of North Side, Grand Cayman, Cayman Islands.

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    $283
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    1 / 17
    5 of 5 stars (13) Excellent
    Old Man Bay
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Watersports Nearby
    • Internet Access
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to On The Bay Condo, located on the ocean’s edge in Old Man Bay, Grand Cayman Island. This is a truly private and tranquil resort, with a lovely white sandy beach, private swimming cove, pool and, of course, the magnificent aqua-blue water of the Caribbean all at your convenience. As... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 1010
    5 of 5 stars Reviewed 24 March 2015
    Lovely condo with perfect location. Away from the crowded 7 mile beach strip, but with beach, pool, views and everything we like. Condo was well appointed and very comfortable.
    5 of 5 stars Reviewed 22 March 2015
    Our first time travelling to Grand Cayman and after staying at The Turtles Next inn and experiencing the island we'll be back for sure. Our condo was first class with all the...
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    $315
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    1 / 12
    5 of 5 stars (39) Excellent
    Old Man Bay
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (39) Make Enquiry
    Amenities & Details
    • Internet Access
    • Water Views
    • Shared Outdoor Pool...
    • Satellite TV
    • Air Conditioning
    • Elevator/Lift access
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This small 12-unit Condo resort is situated in the middle of the north coast of Grand Cayman on a bay dotted with coconut palms. 'On the Bay' has a private sandy beach (swimming) cove, large freshwater pool and is a great value for those looking to be close to everything in East End as well as Rum... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    5 of 5 stars Reviewed 16 May 2015
    We wanted to find a beachfront location away from the crowds at Seven Mile Beach to enjoy the true beauty of the island and this fit the bill perfectly. A comfortable space for 3...
    5 of 5 stars Reviewed 1 April 2015
    On the Bay #205 was the perfect place to stay in Grand Cayman. The location was ideal. This condo is highly recommeded.
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    $1,069
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    1 / 27
    4.5 of 5 stars (11) Very good
    Old Man Bay
    5 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Porch
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    4-5BR/4-5BA Cayman Sands Villa is directly oceanfront in Old Man Bay on the north coast. This very popular villa is one of only 2-3 villas that offers shore-diving (SCUBA) to the famous Cayman Wall. With no coral reef to negotiate, and a sandier beach, SCUBA divers can kick 250 yds. straight out to... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 1202
    5 of 5 stars Reviewed 13 April 2015
    This property was absolutely great. Well appointed with a great kitchen for entertaining our large group. In addition, we loved the screened outdoor area that allowed for many...
    5 of 5 stars Reviewed 3 May 2012
    Amazing relaxed house. Big great room or socializing and nice big bedrooms for getting a bit away. Our extended family of seven had plenty of room. Covered pool was enjoyable even...
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    $1,032
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    1 / 16
    5 of 5 stars (12) Excellent
    Old Man Bay
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Gym
    • Terrace
    • Air Conditioning
    • Balcony
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    4BR/4.5BA Luxury Villa Caymanas is directly oceanfront in Old Man Bay on the north coast. This modern 4 KING SUITE villa offers excellent snorkeling & privacy. The private rear yard around the pool is all white sand for private sunbathing. Enormous oceanfront windows and glass doors to the sea... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 1202
    5 of 5 stars Reviewed 27 July 2014
    Recently stayed at Villa Caymanas this home was amazing, it allowed everyone to enjoy the privacy, space and flexibility that you need to experience the full range of all that...
    5 of 5 stars Reviewed 8 July 2014
    The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and...
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    $315
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    1 / 34
    5 of 5 stars (11) Excellent
    Old Man Bay
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Ocean Views
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Water Views
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Paradise On the Bay provides a serene, comfortable, and soothing vacation in the tropics. Come to our well appointed three bedroom beachfront condo and feel at home. Each bedroom has its own bath. Bring your friends, family, or just yourself to our comfortable, airy piece of heaven on Grand... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 0001
    5 of 5 stars Reviewed 1 July 2015
    This condo is impeccably maintained. Very clean, everything seems brand new. Not tired or in need of repair at all. Large, open, airy – just beautiful. We were also really...
    5 of 5 stars Reviewed 5 January 2014
    I was here with a group of friends for a week over New Year's. What a WONDERFUL experience! It's a half hour drive from Georgetown, about 45 minutes from Seven Mile Beach, and in...
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    $890
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    1 / 16
    4.5 of 5 stars (24) Very good
    Old Man Bay
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (24) Make Enquiry
    Amenities & Details
    • Stereo System
    • Terrace
    • Air Conditioning
    • Porch
    • Private Outdoor...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    4BR/4BA Christmas Palms Villa is directly oceanfront in Old Man Bay on the north coast. This recently built villa offers excellent snorkeling directly behind the oceanfront pool and steps to the beach, which is both sandy and pebbly. Many coral heads hosting schools of juvenile fish await you!... View all property information
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    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    5 of 5 stars Reviewed 29 July 2014
    This place was just as the pictures show. My husband went to celebrate our 35th wedding anniversary with our sons (one with wife and our 11 years old granddaughter, the other's...
    5 of 5 stars Reviewed 22 June 2014
    Just got back from the best vacation we have had in a while. I can't say enough about this house. It was perfect for our family. There were 5 adults and a 7 year old and...
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    $240
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    1 / 11
    5 of 5 stars (10) Excellent
    Old Man Bay
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Escape to the quiet side of Grand Cayman. On The Bay, a small resort on the tranquil North Shore, promises a peaceful Caribbean beach and freshwater pool you’ll often have all to yourself. Yet you’re just a 10-minute drive from the activities at Rum Point. This unit, On The Bay #311, dazzles with... View all property information
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    Location Information
    Old Man Bay, Grand Cayman
    5 of 5 stars Reviewed 20 June 2015
    Nestled away from all the hustle and bustle is Old Man Bay #311. With beautiful views of the Bay and pool which we had to ourselves everyday. Our very own little piece of...
    5 of 5 stars Reviewed 10 April 2015
    This condo was very clean and comfortable. Well outfitted - even had coolers for picnics and everything needed for cooking. Also stocked with charcoal for the grill outside...
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    $179
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    1 / 12
    4.5 of 5 stars (16) Very good
    Old Man Bay
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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 a... View all property information
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    Location Information
    Old Man Bay, Grand Cayman
    4 of 5 stars Reviewed 3 February 2015
    Garden view still had ocean view Very clean ,hot water tank,in condo wifi,washer/dryer Felt right at home Small IGA 10 min east for groceries
    5 of 5 stars Reviewed 29 May 2014
    We thoroughly enjoyed swimming in the pool, snorkelling in the ocean, walking the beach to collect shells. Only a short drive for lunch & dinner but with the option of preparing...
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