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Cayman Islands Luxury Rentals

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    Travelers to Cayman Islands are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    99 Matching Rentals in Cayman IslandsView all 663 rentals
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    Surfers Paradise Oceanfront on the 'New Seven Mile Beach'...come and relax !1 / 102
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Coconut Beach by Grand Cayman Villas and Condos1 / 40
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Heritage House by Grand Cayman Villas and Condos1 / 19
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Two Rainbows by Grand Cayman Villas and Condos1 / 26
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2015
    We just enjoyed a wonderful week with our family at this villa. It is beautifully situated for those who love hanging out on a great beach, playing in the pool, sunbathing...
    Reviewed July 5, 2014
    We have rented many properties and this house had to be one of the best. The house was well kept and very clean when we arrived. The kitchen was top notch as it seemed like it...
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    About this property
    Two Rainbows is one of our most popular 5 bedroom villas. Located in Cayman Kai within the turquoise waters of the North Sound, Two Rainbows offers the sought-after combination of a white sand barefoot beach, breathtaking views, oceanfront freshwater pool, and plenty of privacy. Guests can watch...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Fingertip by Grand Cayman Villas and Condos1 / 17
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2014
    We have stayed in several houses in the Rum Point area and this was the best beach location for a relaxing, private vacation for us and our friends. With two master suites...
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    About this property
    Fingertip is directly waterfront at the end of a sandy point in Cayman Kai on the north coast. This one story, extremely private villa is an excellent choice for a honeymoon, anniversary or just a small family vacation. The property ends in a palm-shaded, white sand beach, with lounge chairs and a...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Tarasand by Grand Cayman Villas and Condos1 / 19
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2015
    We spent 11 nights in July at the Tarasand Villa in Grand Cayman. The place is perfectly put together. Whoever designed the home, the interior and the kitchen amenities, really...
    Reviewed May 28, 2014
    We had two families stay at this home for business conference/vacation purposes. There were 4 adults and 3 children (under the age of 14 years old). The home could have...
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    About this property
    Tarasand sits on the waterfront in Cayman Kai within Rum Point along the north coast. This two-story luxury villa is a great family or couples choice and offers barefoot swimming from its palm-shaded beach. At the end of a quiet cul-de-sac, Tarasand is extremely private and the chances are high...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    'Sun Cloud' Oceanfront Villa in Rum Point!1 / 42
    (15)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Washer
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We booked this for three adults and three kids under the age of 8. The location is on the north side out of the madness of the tourist area. We appreciated it as it allowed us...
    Reviewed April 17, 2019
    Our family of 6 split our time between the ritz Carlton on seven mile beach and suncloud. We debated between the two when we were making plans for spring break and eventually...
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    About this property
    *Featured as one of The London Times' Top 50 villas in the Caribbean* If you're seeking a Caribbean vacation unlike anything you've ever experienced before, come escape to 'Sun Cloud,' a luxury Grand Cayman vacation rental house ideally placed on the island's picturesque North Side in Rum Point....
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Coral Kai by Grand Cayman Villas and Condos1 / 23
    (6)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Washer
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 29, 2016
    This place was as advertised maybe larger then pictured and we had a great time. 10 Adults and a couple of toddlers had lots of room to run and hang out. Outside patio and...
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    About this property
    Coral Kai is directly oceanfront in Rum Point on the north coast. This large one story villa offers a sizable sandy beach that-s perfect for long walks or just a lazy afternoon. Excellent snorkeling is just steps from the back door! The large, oceanfront freshwater pool is elevated, allowing...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Kai Vista by Grand Cayman Villas and Condos1 / 22
    (20)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2015
    Kai Vista was truly a fabulous home for us for the week. Kitchen is fully furnished, bedding and towels all clean and comfortable. Including beach towels so we didn't need to...
    Reviewed July 6, 2014
    Eleven members of my family stayed at Rum Point. We got two villa's with Kai Vista being our main one. I didn't receive one complaint from the entire family. The snorkeling...
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    About this property
    Welcome to Kai Vista! Located in Rum Point along the north coast, this luxe villa sits elevated on a ridge, offers excellent snorkeling off a private sandy beach, features an oceanfront infinity pool and hot tub, and a beachfront sundeck with plush loungers. The homeowners have embraced an...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    Cos Kai by Grand Cayman Villas and Condos1 / 27
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Ocean Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2016
    We absolutely enjoyed our stay at Cos Kai. Four couples. The Great Eight travel together to the Caribbean every 2 years. This was our 8th trip,. Everything was smooth from the...
    Reviewed April 22, 2016
    Our stay at Cos Kai could not have been better. The booking process was easy and seamless. For some reason we felt more comfortable dealing with a company based out of Richmond...
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    About this property
    Welcome to Cos Kai. This two-story luxury villa is a great family or multiple-couple villa choice offering amazing sunsets and barefoot swimming from a palm-shaded beach. Boasting over 6,000 sq. ft., Cos Kai is only a 5-minute walk from the Kaibo Yacht Club to the south and a 10-minute walk to...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    Kai Conut by Grand Cayman Villas and Condos1 / 27
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Parking
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 21, 2015
    There are not many times you rent a home for a group of 10 and end up actually getting what you see on the website. Kai Conut was just that. There was never a time we felt on...
    Reviewed August 13, 2013
    Our stay at the Kai Conut was an excellent experience. Our group included 6 adults and 5 children under 6. Having experience traveling around the world and being routinely...
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    About this property
    Kai Conut Villa is directly sound-front in Cayman Kai, within Rum Point on the north coast. A one-story, private villa with a barefoot swimming beach shaded by palms and Casuarina pines, Kai Conut is perfect for families with small children. Kai Conut's spacious, fully modern living, brand new...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Great Escape by Grand Cayman Villas and Condos1 / 46
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Porch
    • Patio
    • Wi-Fi
    • Ocean Views
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2015
    We really enjoyed our stay at this property but we're disappointed by a few things. First of all, the purple bedroom was listed as a king bed on the site we booked from, but we...
    Reviewed March 3, 2015
    Frist visit to Grand Cayman in January with extended family and were lucky enough to book the Great Escape Villa through Grand Cayman Villas and Condos(.net). Jim offered us an...
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    About this property
    Great Escape is located on a quiet cove in Cayman Kai merely a few steps from the Rum Point Club. This sprawling villa consists of a main house with 3 bedrooms and 2 baths, plus an optional 1 bedroom, 1 bath guest cottage. Rental of both the villa and cottage gives guests two superb master king...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Reef Romance by Grand Cayman Villas and Condos1 / 20
    (10)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Ocean Views
    • Grill
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 2016
    Reef Romance villa on the oceanfront of Rum Point area of Grand Cayman was perfect in every way! The layout of the rooms, all with king size beds and ensure full bathrooms, was...
    Reviewed February 7, 2016
    We stayed at Reef Romance for 10 magical days. Everyday I got to experience waking up in paradise! The views were amazing. The house and location has everything you need to...
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    About this property
    Reef Romance is directly oceanfront in Rum Point on the north coast. A perfect getaway spot for up to five couples, Reef Romance features five king suites, a sizable sandy beach, and excellent snorkeling just steps from the back door! The oceanfront pool, hammocks, and outdoor thatched cabana...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Ocean Kai by Grand Cayman Villas and Condos1 / 27
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 2016
    First of all, let’s get it out there…this house is AMAZING! Our family of 10 (grandparents, ourselves and our college-age kids with their friends) had a relaxing, fun, quality...
    Reviewed July 27, 2015
    This house is stunning and crazy spacious! There was a large group and small children all under age of 7. this house was PERFECT!!!! I cannot explain what a great plan this was...
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    About this property
    Ocean Kai was recently built on the oceanfront in Cayman Kai. Spanning over 5,500 sq ft of lofty living space, with tall ceilings and open concept design, Ocean Kai sleeps 10 guests across 5 bedrooms each with private ensuite bath. Upon entering the great room there is an immediate wow factor as...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Calypso Blue by Grand Cayman Villas and Condos1 / 58
    (6)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2019
    We descended on Calypso Blue with 5 little girls (9,7,5,3 and 5 ms) and 7 adults. My 7 yr old niece declared it the best place ever (as compared to a resort) because we all had...
    Reviewed May 24, 2016
    Stayed at the newly renovated Calypso blue with 9 other adults. Plenty of room for everyone to join together, or to be off on their own comfortably. The beach was amazing, with...
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    About this property
    Calypso Blue has been fully renovated and redecorated, but is still at a reasonable cost for a larger family. Oceanfront freshwater pool with a sandy beach area lead to excellent coral reef snorkeling just steps from the back door. A large oceanfront screened porch is the perfect place to dine or...
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    North Side, Grand Cayman KY1 1202
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Gypsy by Grand Cayman Villas and Condos1 / 25
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gypsy! This beautiful oceanfront villa has been professionally decorated and includes a private pool with elevated views and close proximity to the famous Rum Point Club. Decorated in an elegant Caribbean theme of beach cremes and soft hues, Gypsy is a luxurious island getaway. From the...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Hidden Cove by Grand Cayman Villas and Condos1 / 27
    (1)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Parking
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden Cove is one of the best values on Grand Cayman. Tucked away in a quiet corner of the exclusive Cayman Kai area, Hidden Cove offers a very large family, or two smaller families, a home away from home at very reasonable rates. With a boat dock directly on a secluded cove right on Little...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Housekeeping Included
    • Washer
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Villa Amarone! This spectacular oceanfront home is situated on a sandy beach just minutes from George Town and Seven Mile Beach. Privacy, amenities and excellent snorkeling can be found throughout Villa Amarone, named for the owner's favorite Italian wine. South Sound is a quiet...
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    George Town, Grand Cayman KY1 1202
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    Blue Water Villa by Grand Cayman Villas and Condos1 / 24
    (16)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2018
    We had the best holiday here 2 couples and 4 kids.Staff were so helpful, we arranged for groceries to be at the villa for our arrival and a meal to be cooked the first day. It...
    Reviewed March 31, 2016
    Villa Zara provided a fantastic place to rest our heads and rejuvenate for another day. Our days were spent snorkeling, sailing, kayaking, jet-skiing and eating. We traversed...
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    About this property
    Welcome to Blue Water Villa. This gated estate sits directly oceanfront in Rum Point, along Grand Cayman's north coast. This palatial villa offers a gorgeous pool deck complete with an oceanfront hot tub to soak in and enjoy the sparkling Caribbean views. A large sandy beach with phenomenal...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Fischers Reef by Grand Cayman Villas and Condos1 / 51
    (1)Excellent
    8 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 12, 2019
    Our family group of 15 (ranging in age from 7 months to 91 years!) had a great time at this awesome house. We loved hanging out at the pool and the views are amazing! Thanks...
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    About this property
    Located only 1 mile from the famous Rum Point Club, Fischer's Reef is a perfectly designed 8 bedroom oceanfront villa ideal for large families, or group getaways. Featuring multiple living and sleeping areas--4 king suites, 3 queen suites, a twin bunk suite, and pull-out sofa--the villa-s unique...
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    Rum Point, Grand Cayman KY1 1701
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 20
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    Cayman Castle & Guesthouse by Grand Cayman Villas and Condos1 / 38
    (4)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2015
    We had a great time. The house was unique and suited our needs. It was in excellent condition and everything worked well. We had no issues. The booking was easy and...
    Reviewed June 20, 2014
    June 7-14, 2014. Every other year we take a "family" vacation..large group of 19.. Ages ranging from 65-1. After much research The Castle was just what I was looking...
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    About this property
    Cayman Castle and Guesthouse sits directly oceanfront on a private 2-acre walled estate. Perched on an elevated point of land, the Cayman Castle grounds include an attached private white sandy beach with excellent snorkeling and sunbathing. Infinity pool (heated in the winter), multi-tiered...
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    Location Information
    East End, Grand Cayman KY 1202
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 18
    Amoraflora by Grand Cayman Villas and Condos1 / 37
    (1)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2015
    This was our second trip to Grand Cayman and also to Rum point.We chose Amoraflora to accommodate two families ( myself and my brothers family plus children)Overall...
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    About this property
    Welcome to Amoraflora. This one-of-a-kind oceanfront villa in Rum Point offers a 'mini-resort' experience for large families or vacationing couples (10 adults max, 12 guests total). Made up of two 'L-shaped' single story villas with a common breezeway to the sea, the entire property sits on a...
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    Location Information
    Rum Point, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 12
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Crystal Waters is directly oceanfront on a 200-foot wide barefoot beach in Cayman Kai. Quiet clear waters and panoramic ocean views await in this 5,200 sq foot island getaway. The oceanfront first-floor sunporch spans the entire width of the house, allowing guests to enjoy expansive Caribbean...
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    Rum Point, Grand Cayman KY1 1701
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Picture Perfect by Grand Cayman Villas and Condos1 / 18
    (8)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2016
    There were 10 of us - 3 young children included - and this place worked out really well for us.It was exactly as pictured in the photos. The house is very well located - a short...
    Reviewed February 13, 2016
    We've enjoyed this villa three years in a row because the house, the property, the setting and the location are near to perfect for us. The rooms are spacious; there's plenty of...
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    About this property
    Picture Perfect is the name given to this sunny oceanfront villa by its owner, a professional photographer. Located in South Sound, Picture Perfect is closer to Seven Mile Beach, the airport, and in-town restaurants than the homes located in Rum Point or Cayman Kai. Some of our guests opt not to...
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    Location Information
    George Town, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Cayman Sands by Grand Cayman Villas and Condos1 / 28
    (13)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2019
    The house was better than the pictures. It was very clean and comfortable. The sand was white, the gazebo had a nice breeze for the massages we had out there. The only...
    Reviewed March 30, 2016
    This is a fantastic house right on the beach. They provide every single thing you need to have a fabulous stay. The house was immaculate when we arrived. We were a large group...
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    About this property
    Cayman Sands is an oceanfront villa in Old Man Bay along the north coast. This popular villa is one of only 2-3 homes that offer shore scuba-diving off the famous Cayman Wall. With an open one-story design, Cayman Sands offers an intimate experience across 4,000 sq ft. of living space, plus a one...
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    Old Man Bay, Grand Cayman KY1 1202
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Great Bluff Estates, a gated oceanfront villa with pool set into the bluffs of Grand Cayman's Northside. This recently renovated 5-6 bedroom home offers a large family all they could want from excellent snorkeling steps off the backyard to a stunning elevated sundeck and freshwater...
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    Gun Bay, Grand Cayman KY1 1702
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    4BR Penthouse Boggy Sands Club - Seven Mile Beach1 / 40
    (15)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2019
    I 100% recommend staying at the Boggy Sands Club. Everything was first rate and luxurious!Communication from the start was very easy - we were welcomed by Ruaneik and he...
    Reviewed May 29, 2019
    This was a friends getaway with 8 women staying in the property for 5 nights. I must have read every single review and looked at this listing 1000 times before we actually...
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    About this property
    4 Bedrooms, 4 Bathrooms, Sleeps 10 (King Size, King, Full & Full and 2 Bunk Beds to sleep 4 kids). 2500 Sq feet of Luxury living with private balconies off the living room and master bedroom over looking the pool and pavilion. Penthouse has Ocean Views. 100 Feet from Seven Mile Beach via a Private...
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    Seven Mile Beach, Grand Cayman KY1 1201
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful waterfront home welcomes you to a luxurious private enclave on the Caribbean Sea. Mature palms, ferns, and ornamental shrubbery evoke a tropical feel before you step through the front door. Upon entering the villa, your eyes are drawn through the living room's 40-foot wall of windows...
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    Rum Point, Grand Cayman KY1 1701
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    8 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Orchard Retreat offers individuals, couples, families, and small groups the opportunity to combine a relaxing Caribbean vacation with watersports, eco-excursions, and wellness treatments from private vendors for massage, yoga and more! We maintain a complete list of preferred vendors for many...
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    West Bay, Grand Cayman KY1 1102
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 22
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to On The Rocks! This grand oceanfront gated estate with private pool is conveniently located 20 minutes from the airport in a planned residential community called Beach Bay. The dozen or so homes along this rugged coastline share the key amenity of the neighborhood: a wonderful sandy...
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    Savannah, Grand Cayman KY1 1702
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hilltime is a large single-story beachfront villa located in Rum Point along the north coast of Grand Cayman. The most notable feature of this home-besides the views!-is the vaulted great room's cypress tongue-and-groove ceiling. It's sure to capture your eye as you stare off across the impressive...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Moon Kai by Grand Cayman Villas and Condos1 / 33
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 2013
    I wanted to write a review because this was the most amazing trip we have experienced even with 5 kids under 5. The Cayman Shoppers was perefect! Chet with Empty suitcases.com...
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    About this property
    Moon Kai is a luxury oceanfront villa estate, located on a stretch of the best beach in Cayman Kai. The main house and optional, beautifully-equipped coach house apartment can accommodate a total of 14 people--12 adults max--with 5 expansive oceanfront king suites and a separate queen master...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Sprat Bay Luxury Villa1 / 24
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2019
    Lovely home conveniently located near 7 mile beach, shopping, restaurants and attractions. Sandy, the property manager, was so helpful, kind and available throughout our stay...
    Reviewed April 18, 2019
    This was our first time to the Cayman Island. The trip was a celebration of our 50th wedding anniversary. We wanted to spend a week with our kids and grandkids. This house was a...
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    About this property
    Ocean Front Villa with its own private beach and swimming pool located in South Sound. The villa is constructed on a 20,000 sq ft land in a tropical setting with tall palm trees. The living area is 6,000 sq ft has 3 living rooms, 6 bedrooms and 6 en-suite bathrooms sleeps up to 22 people. The villa...
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    George Town, Grand Cayman KY1
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 22
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Olympus, a majestic contemporary estate masterfully designed and perfectly positioned on a private oceanfront lot in Rum Point. Designed with dramatic white angled walls, three levels of outdoor entertaining spaces, and an oceanfront living area with 40 feet of floor-to-ceiling sliding...
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    Rum Point, Grand Cayman KUY1 1701
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Coral Cottages by Grand Cayman Villas and Condos1 / 26
    (2)Average
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    • Ocean Views
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 30, 2019
    Coral Cottages is a fantastic place to stay if you’re on the island for a week or so and plan to visit the fantastic island restaurants! We do have to admit the description of...
    Reviewed January 5, 2019
    these two side by sides claim to sleep 12, 6 in each house, but that only works if there are 2 in each bed. It would be better if one of the bed rooms had twin beds, so we...
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    About this property
    Coral Cottages Pink & Yellow consists of two pristine villas, full of Cayman character, nestled together right on the oceanfront in Old Man Bay. Each villa has a private oceanfront infinity pool and tranquil garden patio. The vistas across the oceanfront and into the gardens are spectacularly...
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    Old Man Bay, Grand Cayman KY1 1702
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Kaiku by Grand Cayman Villas and Condos1 / 41
    (1)Average
    7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Cable/satellite TV
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    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 17, 2019
    The house is quite nice, and the pool and beach are great. We had a nice vacation with the exception of a major issue: the marble steps and floor in the house are all one...
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    About this property
    Welcome to Kaiku, arguably the most lavish gated estate in all of Cayman Kai. This sprawling villa sits on a double lot consisting of a 5 bedroom main house, and a detached 2 bedroom guest cottage. This luxurious estate can accommodate 15 guests making it the perfect island retreat for a large...
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    Rum Point, Grand Cayman KY1 1202
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 15
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 BR Beachfront villa, with infinity pool. 10 min to 7 miles beach. Free electric car! This beautiful villa is in the private gated community of Conch Point Beach resort, on the northern part of the island, 10 minutes away from Camana Bay and Seven Miles beach. It is as well 5 minutes away from...
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    West Bay, Grand Cayman KY 1 9006
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Seascape - A Luxury Villa on Seven Mile Beach on Grand Cayman, Cayman Islands1 / 36
    (8)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    • Waterfront
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2018
    Seascape sits on a fabulous stretch of Seven Mile Beach. Right out the door we could snorkel and dive-- so many beautiful fish. The location is perfect for restaurants, shopping...
    Reviewed April 3, 2018
    This home is actually a 10 Star!!! It has everything you would want & need & much, much more! I hated to leave! The location is the very best location on 7 mile beach! The...
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    About this property
    Full time manager on property at your disposal. Located in the heart of Seven Mile Beach, where the beach is expansive and breathtaking, and the water is clear and beautiful. No other house of this size is available for rent on this stunning and prestigious stretch of Cayman sand. This is an...
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    Seven Mile Beach, Grand Cayman 92 GT
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 17
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Luna, a luxuriously intimate resort-style community nestled along the coastline just south of Seven Mile Beach. Inspired by Tuscan architecture, Casa Luna blends modern luxury living with an award-winning landscape design to create a secluded Caribbean oasis to call your very own....
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    George Town, Grand Cayman KY1 1100
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Abita Kai (pronounced A-bit-a Kai), an airy oceanfront villa with private pool and new dock on a barefoot, white sand beach in Cayman Kai. The calm shallow waters behind this unique villa offer a wide palette of blue and turquoise colors as well as warm orange sunsets. The most unique...
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    Rum Point, Grand Cayman KY1 17015B
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    8 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Villa Del Mare. This magnificent, Spanish-tiled oceanfront villa is an architectural masterpiece located within a mile of the famous Rum Point Club. After years of neglect, the new owners stripped this villa down to the bones, rebuilding the 10,000 square foot home from the foundation...
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    Rum Point, Grand Cayman KY1 1102
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 22
    Cayman Castle by Grand Cayman Villas1 / 29
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cayman Castle is directly oceanfront on a private 2-acre gated and walled estate on an elevated point of land and enjoys a wide white-sand beach with excellent snorkeling and sunbathing. Infinity pool, multi-tiered oceanfront terraces, panoramic roofed balconies and a covered first floor veranda...
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    East End, Grand Cayman 00000
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to panoramic Far Tortuga. Rentable as a 4, 5, or 6 bedroom villa, this top-10 most popular home is on the north side of the island. With a small grocery store within walking distance, and the Rum Point Club a short drive away, Far Tortuga's location is hard to beat. Oceanfront windows...
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    North Side, Grand Cayman KY1 1202
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    8 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Ayr is a beautiful multi-level beach house with modern interiors and spectacular ocean views throughout. With room for 18 guests, this villa is sure to fit your whole family comfortably. Included with your rental of Southern Ayr is our friendly hospitality staff available to help with...
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    Breakers, Grand Cayman KY1 6021
    Rental Home - 8 Bedrooms, 9 Bathrooms, Sleeps 20
    7 Bedrooms, 6 Bathrooms, Sleeps 17 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    • Ocean Views
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Our Cayman Cottage! This private, spacious, and exquisitely designed beachfront villa sleeps up to 20 guests comfortably. Elegantly built into the majestic cliffs of the East End along the reef-protected northeast coast, this stunning new build provides dramatic elevated views of the...
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    Gun Bay, Grand Cayman KY1 1702
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 17
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Patio
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    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Pease Bay House, a luxurious gated estate located just 20 minutes from the airport. This spectacular home sits along a secluded sandy beach providing exquisite sunsets views. Due to its unique location, Pease Bay House is one of Grand Cayman's best kept secrets for those seeking privacy...
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    Bodden Town, Grand Cayman KY1 1701
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twin Palms is directly oceanfront in the Rum Point district and enjoys a sandy beach and protective coral reef with excellent snorkeling. No neighbors on either side ensure guest privacy. New contemporary 18' x 54' pool and infinity hot tub was built this summer. Pool table and shuffleboard table...
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    Location Information
    Rum Point, Grand Cayman KY1 1202
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • DVD Player
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Villa Mora. This luxurious 7 bedroom, 7.5 bath beachfront gated estate sits on over 200 feet of pristine Grand Cayman beach with fabulous snorkeling and breathtaking sunset views of tranquil South Sound. Spanning over 8,000 sq. ft., this magnificent oceanfront home features ample...
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    Location Information
    George Town, Grand Cayman KY1 1202
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 18
    Rest Azured1 / 8
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Waterfront
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    • Balcony
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2014
    Second trip to this great getaway Island. House was 3 bedrooms plus..very modern baths kitchen and living area. Owner thought about entertaining and location. Would rent again...
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    About this property
    This brand new beach house provides unparallelled luxury in Little Cayman. With 3 bedrooms, 3 full baths and extra room for additional guests, it is the perfect place to bring families and friends for the ultimate Little Cayman experience. Situated on Charles' Bight, the property boasts 120 feet...
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    Little Cayman, Cayman Islands KY3 1003
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Children's Pool
    • Internet Access
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    • Terrace
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean front condo located at the heart of 7 Mile Beach! Newly renovated 3rd floor direct ocean view condo with 3 bedrooms (2 King beds, 2 Twin beds) and 3 bathrooms. Large families can take advantage of the extra queen sleeper sofa available in the living room. This luxury condominium has the white...
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    Location Information
    Seven Mile Beach, Grand Cayman KY1 1202
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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