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Vacation Rentals in Old Man Bay, Cayman Islands and nearby

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    1 / 17
    5 of 5 stars (13) Excellent
    Old Man Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Old Man Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 34
    5 of 5 stars (11) Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    5 of 5 stars (42) Excellent
    Old Man Bay
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool...
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Old Man Bay, Grand Cayman KY1 1001
    5 of 5 stars Reviewed 1 week ago
    We were surprised when entering the condo. We didn't expect that much space and luxury. You can probably get lost in the master bathroom, no kidding! I don't have a lot to add...
    5 of 5 stars Reviewed January 5, 2016
    The property was exactly as advertised, it is clean, very well furnished, it has everything you could possibly want to make your holiday property a home away from home. We arrived...
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    The following rentals are within 5 miles of Old Man Bay, Grand Cayman, Cayman Islands.

    1 / 24
    5 of 5 stars (2) Excellent
    North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
    • Shared Outdoor Pool...
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Indulge in relaxation, recreation, and romance at the “Ocean Pearl” beachfront villa. 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 just nine units and are bordered by the Salina... View all property information
    Location Information
    North Side, Grand Cayman KY1 0001
    5 of 5 stars Reviewed February 29, 2016
    This was our first time to Grand Cayman Island and we cannot wait to go back. It was breath taking, truly a vacation of a lifetime. We cannot even begin to describe how...
    5 of 5 stars Reviewed January 22, 2016
    My wife, sister-in-law, and I had a wonderful experience at the Ocean Pearl. Truly remarkable. The condo is right on a sparkling strip of beach. Besides a few sand pipers and...
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    North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Kiwi Kai is perfect for the couple or family that enjoys tropical open air living. This 910 square foot unit is right on the beach at Cayman Kai, Rum Point, North Side, on the island of Grand Cayman. You will be a few steps from snorkeling, swimming or wading in the crystal clear Caribbean Sea.... View all property information
    Location Information
    North Side, Grand Cayman KY1 1102
    1 / 24
    5 of 5 stars (2) Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Housekeeping...
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    North Side, Grand Cayman KY1 1701
    5 of 5 stars Reviewed April 23, 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...
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    1 / 20
    5 of 5 stars (56) Excellent
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 stars Reviewed 2 weeks ago
    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...
    5 of 5 stars Reviewed June 20, 2016
    I have stayed in Grand Cayman many times but this was the first time at Cayman Kai and what luck booking Beachfront! This property is ideally located next to the Kaibo Bar and...
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    1 / 48
    5 of 5 stars (30) Excellent
    North Side
    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 KY1 1105
    5 of 5 stars Reviewed May 1, 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 March 1, 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 / 13
    5 of 5 stars (13) Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    North Side, Grand Cayman KY2 1101
    5 of 5 stars Reviewed March 8, 2016
    This is the second trip for our family staying at Azure Breeze. It’s quiet and family friendly. You are right on the beach with a gorgeous view. The kids played in the sand...
    5 of 5 stars Reviewed February 23, 2016
    This rental was perfect for our needs. We always look for somewhere on the beach, no far from a grocery store, that is good for three generations of family. This rental was...
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    1 / 34
    5 of 5 stars (19) Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • 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 KY1 9006
    5 of 5 stars Reviewed April 26, 2016
    My husband and I stayed at NBT with our two children (2 year old and 9 Month old) and my mother in law (Nana). The house was the perfect lay-out for us, we all had our own space...
    5 of 5 stars Reviewed January 26, 2016
    We arrived Sunday, January 10, 2016 and got our rental car (which you will need as the house is about 40 minutes from airport). Also note, all grocery stores are closed on...
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    1 / 11
    5 of 5 stars (7) Excellent
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    North Side, Grand Cayman KY1 1701
    4 of 5 stars Reviewed August 18, 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 May 16, 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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    1 / 34
    5 of 5 stars (31) Excellent
    North Side
    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 KY1 1107
    5 of 5 stars Reviewed July 17, 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 April 30, 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 / 24
    5 of 5 stars (12) Excellent
    North Side
    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 KY1 9006
    5 of 5 stars Reviewed August 19, 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...
    5 of 5 stars Reviewed August 13, 2015
    I'm sitting in the living room of the Coral Loft as I type this review. The house is amazing... so bright and clean. The furnishings are beautiful and modern with a beachy feel...
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    1 / 8
    4 of 5 stars (1) Very good
    North Side
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 Kaibo's restaurants,... View all property information
    Location Information
    North Side, Grand Cayman KY1206
    4 of 5 stars Reviewed June 12, 2016
    If your looking for a house to share with friends or family members in a quiet, remote rental with all the amenities right down to a gas barbecue grill and a potato peeler this is...
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    1 / 23
    North Side
    6 Bedrooms, 7 Bathrooms, Sleeps 15 | Quick View
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    • Internet Access
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Coco Kai is a newly remodeled 6 bedroom, 6 and a half bathroom property, along with two living rooms, separate dining space, breakfast bar, brand new kitchen with new upgraded appliance and remodeled bathrooms. New furniture has been installed throughout. Every room has been redecorated, including... View all property information
    Location Information
    North Side, Grand Cayman KY1 1202
    1 / 28
    5 of 5 stars (34) Excellent
    North Side
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • 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 stars Reviewed 2 weeks ago
    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...
    5 of 5 stars Reviewed September 2, 2015
    This house on the north side of the island was a wonderful place to enjoy the beauty of Grand Cayman and the company of friends! If you are looking for the excitement of seven...
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    1 / 16
    5 of 5 stars (33) Excellent
    North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • 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
    5 of 5 stars Reviewed 4 weeks ago
    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 May 18, 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
    North Side
    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 KY 1006
    5 of 5 stars Reviewed April 5, 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 March 15, 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
    North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 stars Reviewed July 24, 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 April 12, 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 / 23
    North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
    • Internet Access
    • Parking
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This exclusive, brand new 3 bedroom beach front villa in North Side, has been beautifully decorated with state of the art fixtures and fittings for your ultimate comfort and convenience. This ultra-modern villa with its sleek design features its own private pool and BBQ, along with two kayaks that... View all property information
    Location Information
    North Side, Grand Cayman KY1 1001