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Holiday Homes and Apartments Old Man Bay, Cayman Islands and nearby

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    All 23 Rentals in the Old Man Bay Area
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    $267
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    1 / 25
    Old Man Bay
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $1,166
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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
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    $970
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    1 / 16
    4.5 of 5 stars (24) Very good
    Old Man Bay
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    $309
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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 25 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 23 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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    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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    Old Man Bay, Grand Cayman KY1 1001
    5 of 5 stars Reviewed 17 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 2 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 / 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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    Old Man Bay, Grand Cayman KY1 0001
    5 of 5 stars Reviewed 2 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 6 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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    1 / 24
    5 of 5 stars (12) Excellent
    Old Man Bay
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Private Fishing...
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    • Water Views
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Northern Lights Condos is a privately owned and operated nine-unit condominium complex situated on the edge of the ocean on Grand Cayman's quiet north coast. The beauty and comfort of these units are only matched by their natural surroundings; 240 feet of sandy beach, a coral reef teeming with... View all property information
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    Location Information
    Old Man Bay, Grand Cayman CAYMAN ISLANDS
    5 of 5 stars Reviewed 19 April 2015
    Highly recommend! We were with our 2 sons, ages 10 and 12, and this condo had everything we could have asked for and more. The views were spectacular, snorkeling right off the...
    5 of 5 stars Reviewed 3 January 2015
    We could not have asked for a better place to stay to satisfy our quest for sun, fun, and relaxation. The North side of the Cayman Islands has a gorgeous reef with outstanding...
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    $1,125
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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 28 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 9 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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    $262
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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 11 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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    $195
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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 4 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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    The following rentals are within 10 kilometres of Old Man Bay, Grand Cayman, Cayman Islands.

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    1 / 34
    5 of 5 stars (31) Excellent
    North Side
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (31) 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 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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    $978
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    1 / 28
    5 of 5 stars (32) Excellent
    North Side
    6 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Reviews (32) 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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    Location Information
    North Side, Grand Cayman KY1 1702
    5 of 5 stars Reviewed 29 July 2015
    This was probably one of the best homes we have stayed in with our family. 8 adults and 3 children under the age of 4. Plenty of room for everyone. Pool used every day, dock and...
    5 of 5 stars Reviewed 27 July 2015
    This place is on the quiet north side of the island- has a patch of sandy beach, a small pool, and most importantly a dock with a cabana and a hammock (great breezes there), with...
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    $775
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    1 / 12
    4.5 of 5 stars (3) Very good
    North Side
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    4BR/3.5BA Castaway Cove Villa is directly oceanfront in the district of Northside and enjoys a protective coral reef with excellent snorkeling. Two-Story oceanfront windows and doors flood this villa with Caribbean sunshine. Vaulted ceilings, french doors to oceanfront deck and open architecture... View all property information
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    Location Information
    North Side, Grand Cayman KY1 1202
    From
    $459
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    1 / 15
    4.5 of 5 stars (4) Very good
    North Side
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    3BR/3BA - Mahogany Point is directly oceanfront in the district of Northside and enjoys a protective coral reef with excellent snorkeling. Living room and master bedroom sliding glass doors bring in lots of Caribbean sunshine. A charcoal BBQ, central A/C, lounge chaises, and WiFi Internet access... View all property information
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    Location Information
    North Side, Grand Cayman 00000
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    $377
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    1 / 13
    5 of 5 stars (9) Excellent
    North Side
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Watersports Nearby
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Snorkel right outside your villa on the quieter north side of Grand Cayman - where you will enjoy cooling sea breezes (the a/c is often a choice, not a necessity!) and breathtaking uninterrupted views of the ocean. No traffic jams, just the gentle sound of the waves breaking on the reef to lull you... View all property information
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    Location Information
    North Side, Grand Cayman KY2 1101
    5 of 5 stars Reviewed 22 March 2015
    No, really, we were hoping there would be oregano -- there was. We were hoping the knives would be sharp and that the dishwasher really washed dishes -- yup. We were hoping you...
    5 of 5 stars Reviewed 24 February 2015
    As a long time vaction rental patron, I found this house on the beach to be exactly what I wanted and expected. The house was in perfect order, included everything we needed for...
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    $823
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    1 / 24
    5 of 5 stars (10) Excellent
    North Side
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Ocean Views
    • Water Views
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    North Side, Grand Cayman KY1 9006
    5 of 5 stars Reviewed 2 June 2015
    The house is gorgeous, spacious, and well appointed but cannot hold a candle to that view from the pool. Such an elegant, peaceful atmosphere.
    5 of 5 stars Reviewed 12 May 2015
    They say it's fun to have fun but you have to know how. Well, Coral Loft will teach you - it is a simply fabulous property about 45 minutes drive away from the 'bustle' of George...
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    1 / 11
    5 of 5 stars (7) Excellent
    North Side
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (7) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located just 5 miles from Rum Point, directly on the sparkling Caribbean Sea, #2 Azure Breeze Villas is situated in North Side, Grand Cayman. This newly decorated beachside villa has breathtaking panoramic ocean and beach front views from both the ground floor living area as well as from the... View all property information
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    Location Information
    North Side, Grand Cayman KY1 1701
    4 of 5 stars Reviewed 19 August 2013
    This villa is perfectly placed on the North Side of the island, away from built up busy tourist areas. There is fantastic unspoilt reef a short way into the ocean at the back of...
    5 of 5 stars Reviewed 17 May 2013
    As you can see in the photos, the six villas at Azure Breeze are located on their own private beach, surrounded by lovely palms and other seaside greenery. Northside is a very...
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    $240
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    1 / 13
    5 of 5 stars (11) Excellent
    North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Water Views
    • Waterfront
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This luxury vacation condo rental is located on the second floor of the North Pointe Condominium building, which houses only 10 units. Freshly remodeled and decorated, Cayman Stead offers luxury accommodations for your Caribbean Island vacation in paradise! This air-conditioned ocean view condo... View all property information
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    Location Information
    North Side, Grand Cayman KY1 1701
    5 of 5 stars Reviewed 31 March 2015
    We just returned from spending a week at Cayman Stead. Jackie was very prompt to address all my questions prior to our departure, and she provided great information on the area on...
    5 of 5 stars Reviewed 3 March 2015
    We fortunate enough to stay here for two months this winter! This unit has a well equipped kitchen for someone that wants to do a little cooking. The pans are not so thin that...
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    $341
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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 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 16 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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    $206
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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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    Location Information
    North Side, Grand Cayman KY11007
    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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    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 19 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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    5 of 5 stars (2) Excellent
    North Side
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • DVD Player
    • Watersports Nearby
    • Ocean Views
    • Housekeeping...
    • Wi-Fi
    • Water Park Nearby
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Gorgeous crystal clear waters right out the back door! Eighty feet from the sliding doors is the best snorkeling on the island, between the shore and a beautiful coral reef, in shallow water that is easy to navigate. There are endless colorful fish and beautiful coral heads for exploring. Azure... View all property information
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    Location Information
    North Side, Grand Cayman KY1 1701
    5 of 5 stars Reviewed 24 April 2015
    We had a fantastic vacation at the Hartzell Azure Breeze #3! Before we started our trip, they provided home info, sites to see, medical info., dining recommendations, and Chris...
    5 of 5 stars Reviewed 21 April 2015
    We stayed for nine days at Azure Breeze 3. The house was great and had everything we needed and more! We loved taking out the kayak into the ocean and exploring the reefs. We...
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    $315
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    North Side
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Wi-Fi
    • Water Views
    • Watersports Nearby
    • Ocean Views
    • Hot Tub
    • Housekeeping...
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront townhome. Here you can discover the natural side of Grand Cayman, escape your busy life and enjoy peace and tranquility. Part of the Northern Lights development, we are one of only nine units and are bordered by the... View all property information
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    Location Information
    North Side, Grand Cayman KY1 0001