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Cayman Islands Luxury Holiday Rentals

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    Travellers to Cayman Islands are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    64 Matching Rentals in Cayman IslandsView all 429 rentals
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    About this property
    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** This remarkable Cayman Kai villa near Rum Point boasts 8,000 square feet of modern Balinese style luxury – a private compound...
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    Rum Point, Grand Cayman KY1 1001
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    Coral Reef1 / 24
    (10)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 November 2017
    Excellent trip, house is perfect! We stayed there previously, but since the remodel it is even better if that's possible. Can't wait to go back!
    Reviewed 20 August 2014
    Just saying this could be one of the best properties on 7MB. A representative of the owner family "Jim" lives in an apartment on the first floor and was available...
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    About this property
    On prestigious Seven Mile Beach there are very few private villas for rent. Coral Reef, is one of the phenomenal homes! Completely renovated and expanded this villa is now a spectacular 7-bedroom (with bonus Game Room) and 7.5-bath beachfront mini-resort located on the most sought after beach in...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 25
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    FALL SPECIAL - Elegant 7BR Estate - Kaia Kamina by Luxury Cayman Villas1 / 41
    (5)Excellent
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Waterfront
    • Hot Tub
    • Washer
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2017
    Kaia Kamina was a dream come true. Waking up to glorious views of the ocean and a clean private beach, sparkling infinity pool and spacious bedrooms and bathrooms was the...
    Reviewed 21 November 2016
    What a stunning, brand new ultra luxurious beach villa. Very private, plenty of space for large groups. Spectacular views, open plan and superb entertaining/dining spaces. Very...
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    About this property
    *** FALL SPECIAL — Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. — 'Ask the Manager' for details. *** Luxury Cayman Villas proudly presents 'Kaia Kamina,' located in the resort community of Cayman Kai, near Rum Point, on Cayman's...
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    Grand Cayman, Cayman Islands KY1 1302
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    FALL SPECIAL - 6BR Oceanfront Estate - Point of View by Luxury Cayman Villas1 / 45
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2017
    Close to central George Town, this villa was situated int he best location. The rooms were amazingly spacious and really comfortable. Everything was state of the art. I loved...
    Reviewed 29 January 2017
    Last year we rented "Present Moments", this year "Point of View" . The home was above and beyond expectation. It was beautifully appointed, fully automated...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Introducing Point of View, a magazine-worthy South Sound villa that helps you focus on what's important: untouched natural...
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    George Town, Grand Cayman KY1 1302
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Seascape - A Luxury Villa on Seven Mile Beach on Grand Cayman, Cayman Islands1 / 36
    (7)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    • Waterfront
    • Patio
    • Ocean Views
    • Cable/satellite TV
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    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 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...
    Reviewed 31 December 2017
    We rented this house for a week over the holidays with a family of 12 people aged 16 to 80 and there was plenty of room for everyone to thoroughly enjoy a beach vacation. This...
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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
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 17
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    6BR-Moon Kai1 / 24
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed 17 July 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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 coachhouse...
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    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    FALL SPECIAL - 6BR in Cayman Kai - Sun Salutations by Luxury Cayman Villas1 / 50
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2017
    This was the perfect setting and home for our group. We couldn't have asked for anything else in a vacation home. The kayaks and SUP were a lovely extra and the management...
    Reviewed 12 June 2017
    The location is amazing. If feels like you have a private beach, but you are in walking distance of the always happing Rum Point. The home is gorgeous, and very spacious...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** 6BR/6.5BA Sun Salutations is a popular premier villa in Cayman Kai. The villa is directly oceanfront in Cayman Kai (within Rum...
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    Grand Cayman, Cayman Islands 11003
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 18
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    FALL SPECIAL - 12,000 sq.ft. 6BR Estate - Oceanus by Luxury Cayman Villas1 / 39
    (2)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 23 Quick View
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    • Air Conditioning
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    This was my third trip to Grand Cayman, but probably my favorite. We stayed at a rental home, Oceanus, on the south side of the island, on Frank Sound. The location was great...
    Reviewed 28 October 2017
    Oceanus was amazing. The property was perfect for an island getaway. Fantastic amenities and very spacious. Considering a larger family getaway here next year. View of the...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Introducing Oceanus, where luxury, elegance and seclusion converge. This modern masterpiece has a contemporary design. The...
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    Grand Cayman, Cayman Islands KY1 1001
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 23
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    FALL SPECIAL - 7BR Oceanfront Masterpiece - Evolution by Luxury Cayman Villas1 / 48
    (7)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
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    Pet friendly
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    Reviewed 16 February 2018
    An amazing home which became the perfect venue for my 50th birthday celebration. The owner spared no expense in furnishing his place. It was so comfortable for us 14 adults...
    Reviewed 1 February 2018
    This house is amazing. And I mean take your breath away amazing!We were lucky enough to stay here for a week in January and we couldn’t have pick a better place to stay.I...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Inhale, exhale and arrive at Evolution, a seven-bedroom, seven and a half bath villa on a wide stretch of natural beach in...
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    Bodden Town, Grand Cayman 12345
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    FALL SPECIAL - 6BR Modern Oceanfront Tranquility Cove by Luxury Cayman Villas1 / 36
    (15)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
    • Patio
    • Washer
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    This house, location, and size was absolutely perfect. It was luxurious yet very comfortable. We could not have asked for more!! We have stayed in several beach houses in Cayman...
    Reviewed 10 July 2018
    We booked Tranquility Cove for a mum’s relaxation weekend. It was everything and more than we could have imagined. Tranquility Cove is a stunning property and we did not want to...
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    About this property
    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Sweeping, clean-lined spaces meet stunning sea views at our 6-bedroom, 6.5-bathroom villa set on a large stretch of barefoot...
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    Grand Cayman, Cayman Islands KY1 1302
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    FALL SPECIAL - 7BR Colonial Estate - Tatenda by Luxury Cayman Villas1 / 44
    (11)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    This house is just stunning, and it was a wonderful choice for our large group of multiple families traveling together. The staff was so helpful, and the accommodations were...
    Reviewed 30 April 2018
    To say we were pleased with our stay at Tatenda is an understatement. We were blown away by the modern, upscale, newly renovated house. With no detail overlooked, our stay at...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Luxury Cayman Villas proudly presents “Tatenda,” a colonial estate located in the prestigious community of South Sound on...
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    Location Information
    George Town, Grand Cayman KY1 1111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 15
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    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Welcome to Pease Bay House, a secluded luxurious gated estate only 20 minutes from the airport. This spectacular home sits along a private sandy point of beach facing southwest for exquisite sunsets views. Spanning 6,000 sq. ft. across 5 bedrooms (3 king suites, 1 queen and 1 twin bedroom) and...
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    Cayman Islands, Caribbean KY1 1202
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    8 Bedrooms, 10 Bathrooms, Sleeps 20 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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....
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    Grand Cayman, Cayman Islands KY1 1701
    Holiday Rental House - 8 Bedrooms, 10 Bathrooms, Sleeps 20
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    Majestic Luxury Private Home On Seven Mile Beach1 / 37
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    George Town, Grand Cayman 30743
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 17
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Secure Parking
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    • Private Outdoor Pool (Unheated)
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    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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    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Terrace
    • DVD Player
    • Balcony
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    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 outdoor...
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    George Town, Grand Cayman KY1 1702
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    FALL SPECIAL - Chic 4BR Balinese - Stepping Stone by Luxury Cayman Villas1 / 47
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2018
    There is not one thing out of place in this palace on the beach. The attention to detail is something you don't even find in 5 star hotels! You have all the amenities that you...
    Reviewed 3 June 2018
    This stunning beach house exceeded our expectations. From the secluded location, amazing views of the ocean (with or without the walls of windows open), the large common room...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** This sexy, Balinese-style oceanfront luxury home is one of the most spectacular residences in all of East End. Boasting...
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    Grand Cayman, Cayman Islands 10001
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    FALL SPECIAL - 5BR Oceanfront Estate - Nirvana by Luxury Cayman Villas1 / 39
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2017
    WOW! That's the first thing that comes to mind when driving through the gate to Nirvana. Private, spotless, breathtaking, just a few words to describe this villa. Kayaks and...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Luxury Cayman Villas proudly presents 'Nirvana,', a one-of-a-kind, eco-chic oceanfront estate affording complete privacy,...
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    George Town, Grand Cayman 11302
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    7BR-Cayman Castle1 / 27
    (4)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed 11 September 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 20 June 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Rum Point, Grand Cayman KY1 1202
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Hot Tub
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    • Secure Parking
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Sea Orchard Retreat offers individuals, couples, families and small groups the opportunity to combine a relaxing Caribbean vacation with opportunities for...
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    West Bay, Grand Cayman KY1 1102
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 22
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to the Caribbean Club 4 Bedroom Villas represented by Exceptional Villas. Welcome to our Four Bedroom Villas at the Caribbean Club, a luxurious and exclusive beachfront paradise located directly on the famous Seven Mile Beach in Grand Cayman. The Caribbean Clubs Villas are the most...
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    Seven Mile Beach, Grand Cayman 19°19 52 9 N 81°22 53 9 W
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Ocean Kai1 / 28
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 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 27 July 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Rum Point, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Water's Edge has set a standard of luxury on 7 Mile Beach that has gone above and beyond with exquisite beach front apartments and amenities. Located on the fifth floor, this 3 bedroom, 3 bathroom beach front villa has stunning views of the soft white powdery beach and glistening waters of the...
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    Location Information
    West Bay, Grand Cayman KY1 1000
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
    • Washer
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    • Wi-Fi
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful yet comfortable luxury home. High quality furnishings and fixtures. As expressed in our reviews (see home Away), the view of South Sound from our oceanside location is stunning. Some of our guests enjoy just chilling on the patio with the pool and the barbeque, paddleboarding, or...
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    George Town, Grand Cayman KY
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Much thought went into the concept and design of these exceptional homes — and it shows! From the Tuscan-inspired architecture...
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    George Town, Grand Cayman 10001
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Faroway is a gorgeous, single-story, 5,000 sq. ft. luxury oceanfront villa on Grand Cayman’s South Sound, with an oceanfront...
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    George Town, Grand Cayman KY11001
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    FALL SPECIAL - 4BR on Seven Mile Beach - Serenity Now by Luxury Cayman Villas1 / 76
    (29)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Patio
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2018
    We loved this house and enjoyed our vacation. However, be warned, there is NO SAND BEACH in front of the house. It is very rocky and hard to navigate by foot. We had several...
    Reviewed 20 March 2017
    Two families (with 6 kids ranging from 18 to 11 years old) spent a relaxing and fun filled week at Serenity Now in the Caymans. 100% agree with all the positive reviews listed...
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    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** RECENTLY RENOVATED!! We jumped at the chance to offer guests their own villa on the north end of Seven Mile Beach – a rare...
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    Location Information
    West Bay, Grand Cayman KY1 1302
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Terrace
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** ==10% New Listing Discount Extended Thru December 15, 2018== Welcome to Great Bluff Estates, a gated oceanfront villa with pool set into the bluffs of Grand Cayman’s...
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    Gun Bay, Grand Cayman KY1 1702
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Serenity Now, a stunning 4 bedroom beachfront villa on the world famous Seven Mile Beach in Grand Cayman. Serenity Now is such a unique and charming home perched in the quiet and serene Northern side of Seven Mile Beach. Serenity Now is located in what is considered to be one of the...
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    Location Information
    West Bay, Grand Cayman 19 368354 81 400017
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Hot Tub
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    Pet friendly
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    About this property
    Welcome to The White Cottage Villa in Grand Cayman, your serene slice of paradise at the 5 bedroomed, White Cottage Villa located in East End, Grand Cayman. A mere 26km from Owen Roberts International Airport (GCM), this beautiful, self-contained, contemporary property is an air-conditioned...
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    East End, Grand Cayman 19°18 01 2 N 81°09 49 4 W
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5BR-Cos Kai1 / 24
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed 24 April 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 22 April 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Rum Point, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    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. Cos Kai is only a 5-minute walk from the Kaibo Yacht Club to the south and a 10-minute walk to the Rum Point Club to the north....
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    Location Information
    Rum Point, Grand Cayman 19 360416 81 274124
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    Our Cayman Cottage1 / 27
    (1)Very good
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    We stayed in this beautiful home for a week in July. Upon arrival, it was about 90 degrees in the house. We found quickly that the home does not have central air. This was...
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    About this property
    This spacious, exquisitely designed beachfront home has 7 bedrooms and 5.5 bathroom. This wonderful home can comfortably sleeps up to 18 guests. The home spans across four levels for a total of 8,000 interior square feet and an additional 2,000 square feet of outside space on the gorgeous pool...
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    Gun Bay, Grand Cayman KY1 1002
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** The main level consists of your interior lounge, dining, kitchen, guest bedroom with ensuite and powder bath, leading to your...
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    Rum Point, Grand Cayman 11103
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    7BR-Crystal Blue1 / 27
    (2)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2015
    This home and its location were absolutely perfect for our family. Our family of eight, which included two children, really appreciated the layout of this absolutely stunning...
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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Crystal Blue is a magnificent, private cliff-edged, gated villa with private pool and stone steps to the water below. Guests will not see another person behind the...
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    East End, Grand Cayman KY1 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Crystal Waters is directly oceanfront on a 200' wide barefoot beach in Cayman Kai. Quiet clear waters and panoramic ocean views await in this 5,200 sq foot island...
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    Rum Point, Grand Cayman KY1 1701
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5BR-Two Rainbows1 / 25
    (5)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 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 5 July 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Location Information
    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5BR-Coral Kai1 / 24
    (6)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed 29 February 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Location Information
    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4BR-Villa Zara1 / 54
    (15)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 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...
    Reviewed 22 July 2015
    This house is truly incredible. Perfect location and everything we were looking for in comfort, room and features. Caretakers are Phil and Yvonne and they are simply fantastic...
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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** Welcome to Villa Zara. This gated estate sits directly oceanfront in Rum Point, along Grand Cayman's north coast. This palatial villa offers a gorgeous pool deck...
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    Grand Cayman, Cayman Islands KY1 1202
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Reef Romance1 / 24
    (10)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 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 7 February 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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    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** 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...
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    Rum Point, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    *** FALL SPECIAL - Join us this fall and stay 5 nights for the price of 4 or 7 nights for the price of 5. Terms and conditions apply. - 'Ask the Manager' for details. *** Much thought went into the concept and design of these exceptional homes — and it shows! From the Tuscan-inspired architecture...
    View all property information
    Location Information
    George Town, Grand Cayman 10001
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • Air Conditioning
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** FALL SALE - STAY 5 NIGHTS FOR THE PRICE OF 4 Book a 5 night stay between Nov. 26 - Dec. 14, 2018, and enjoy one night free!*** ==10% New Listing Discount Extended Thru December 15, 2018== Welcome to On The Rocks! This grand oceanfront gated estate with private pool is conveniently located 20...
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    Savannah, Grand Cayman KY1 1702
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 private bedrooms 2 ensuite plus full use of our spacious house in a secure gated community. We have modern furnishings inc fully equipped kitchen, a pool and a moroccan conservatory. Just 9 min walk to the beach. The space: You will have your own private bedroom (with views of the palm trees...
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    Location Information
    Seven Mile Beach, Grand Cayman KY19006
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a beautiful pristine section of Seven Mile Beach, Sea Breeze is a boutique condo development of just nine luxury corner condos with incredible ocean views. Condo 3 is located on the second floor and can sleep up to 10 guests in comfort (and can be rented alongside condo 4 next door for...
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    Location Information
    Seven Mile Beach, Grand Cayman KY1 1207
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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