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Cayman Islands Holiday Rentals with Pools

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    Travellers to Cayman Islands are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    232 Matching Rentals in Cayman IslandsView all 358 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Caribbean Paradise 91 / 12
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Coral Reef1 / 24
    (10)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 25 Quick View
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    Lacovia #61 / 23
    (20)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Waterfront
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Claim a prime spot on the beach at Lacovia, a small-scale beachfront resort in the heart of sought-after Seven Mile Beach on Grand Cayman. This 3-bedroom, 3-bath apartment, Lacovia #6, sleeps up to 8 guests in ocean-view comfort. At Lacovia, find resort amenities like a pool and hot tub, tennis...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Rocky Shore Villas, a true getaway in the heart of West Bay. Here you will find your own piece of rural Grand Cayman, in close proximity to Cobalt Coast resort, Ironshore walk and Barker’s National Park Rocky Shore Villas comprise of seven separate properties, plus the host’s home and...
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    West Bay, Grand Cayman KY1 1302
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Villa La Playa1 / 27
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    This authentic Caymanian gem in the quiet residential neighbourhood of Cayman Kai will charm you with its waterfront location, swimming pool, traditional island architecture, distinctive paint colours, and surprisingly spacious interior with 4 bedrooms, 4.5 baths and an open-concept floor plan. All...
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    North Side, Grand Cayman KY1 1202
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    7 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Hot Tub
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** SUMMER SPECIAL — Join us this summer and receive 10% PLUS indulge in the best Grand Cayman has to offer on land and sea with your choice of a half-day boat excursion to Stingray City; a private family cooking class and dinner; or a $750 in-villa spa credit toward the services of your choice!...
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    Grand Cayman, Cayman Islands 10001
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 22
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
    • Grill
    • Balcony
    • Children's Pool
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    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Premier Morritt's Tortuga Club resort offers a luxury beach front paradise atmosphere, with 2 pools a waterfall and swim up cocktail bar. Each air conditioned apartment has a balcony and a fully equipped kitchen. The property's restaurant serves gourmet food and there are several bars. Many...
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    East End, Grand Cayman KY1 1106
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    • Housekeeping Included
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If peace and quiet, diving, snorkelling and spelunking is your passion, you will love Kings Point, Cayman Brac. Located on the oceanfront, backed by the bluff, Kings Point is located on the southeast shore, near Great Cave and the blow holes at the end of the island. It is quite private and...
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    Cayman Brac, Cayman Islands CAYMAN BRAC
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SUMMER SPECIAL—7BR Colonial Estate—Tatenda by Luxury Cayman Villas1 / 44
    (7)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** SUMMER SPECIAL — Join us this summer and receive 10% off PLUS indulge in the best Grand Cayman has to offer on land and sea with your choice of a half-day boat excursion to Stingray City; a private family cooking class and dinner; or a $750 in-villa spa credit toward the services of your...
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    George Town, Grand Cayman KY1 1111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Waterfront
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    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A vacation at Summer Breeze is the perfect way to get away from it all. Located in the exclusive Cayman Kai area, it is nestled between a beautiful blue water cove and the famous Rum Point Beach. With it's open-air island styling, the house lets in summer breezes all year long. Summer Breeze just...
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    Grand Cayman, Cayman Islands BWI
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nested on a quiet cove amid lush tropical foliage, this is a perfect place for a family or a romantic get-away. An open design Island House that brings nature and the island breeze indoors. Island Sunset, is only steps away from the famous Rum Point Beach where water sports, swimming or hammocks...
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    Grand Cayman, Cayman Islands GRAND CAYMAN
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SUMMER SPECIAL—6BR Cayman Kai Estate—Sun Salutations by Luxury Cayman Villas1 / 50
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    • Air Conditioning
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** SUMMER SPECIAL — Join us this summer and receive 10% off PLUS indulge in the best Grand Cayman has to offer on land and sea with your choice of a half-day boat excursion to Stingray City; a private family cooking class and dinner; or a $750 in-villa spa credit toward the services of your...
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    Grand Cayman, Cayman Islands 11003
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 18
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    Seven Mile Beach Condo1 / 21
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing 2 bedroom, 2 bath condo, fully stocked on the 'Seven Mile Beach' in Grand Cayman! ! Savor the stunning sunsets from the screened in porch. Engage in an invigorating barefoot stroll or run along the powdery beach at sunrise. Regal Beach #631 is a legendary location renowned for its exquisite...
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    Seven Mile Beach, Grand Cayman KY1 1200
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Air Conditioning
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    • Balcony
    • Grill
    • Terrace
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean view condo located at the heart of 7 Mile Beach Newly renovated ground floor direct ocean view condo with two bedrooms (1 King bed + 2 Twin beds) and two bathrooms. Large families can take advantage of the extra Queen Sleeper Sofa available in the living room. This luxury condominium has the...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Rum and Kai - TripAdvisor Rum Point Award Winner1 / 52
    (47)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • Air Conditioning
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    • Ocean Views
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    • Shared Outdoor Pool (Unheated)
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at 'Rum and Kai', at the Retreat in Rum Point. This beach front 1 bedroom condo is located in the stunning upscale vacation home enclave of Cayman Kai on beautiful Grand Cayman. Thanks to our discerning guests, we have recently been designated as a TripAdvisor and FlipKey...
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    Rum Point, Grand Cayman KY1 1701
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Air Conditioning
    • Grill
    • Balcony
    • Terrace
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean view condo located at the heart of 7 Mile Beach Newly renovated ground floor direct ocean view condo with two bedrooms (1 King bed + 2 Twin beds) and two bathrooms. Large families can take advantage of the extra Queen Sleeper Sofa available in the living room. This luxury condominium has the...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Caribbean Paradise #121 / 22
    (8)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    • Internet Access
    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find paradise at this 3-bedroom, beachfront villa with a spacious back deck shaded by palm trees and looking out over the Caribbean Sea. Enjoy a memorable oceanfront barbeque with burgers on your private gas grill, and then kick off your flip-flops for a sunset stroll along the shore. This stretch...
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    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beachfront, 7 Mile Beach, Discovery Point Club1 / 12
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
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    • Waterfront
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This condo is located on the quiet north end of Seven Mile Beach. You are steps from the beach and the clear blue water of the Caribbean. Swim or snorkel right outside your condo. Relax on the uncrowded beach, soaking up the sun or in the shade of a thatched hut. There is a beachfront swimming pool...
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    Seven Mile Beach, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cayman Conch Quest Beachfront Condo in Rum Point1 / 11
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • Air Conditioning
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    • DVD Player
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cayman Conch Quest! Our first floor location has great unobstructed views of the Caribbean Sea and direct access to the beach and pool, both only steps from the private lounging deck. Enjoy your meals in the screened lanai where the sights and sounds of the ocean will make you wish...
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    Grand Cayman, Cayman Islands KY1 1700
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean view condo located at the heart of 7 Mile Beach Newly renovated 2nd floor direct ocean view condo with two bedrooms (1 King bed + 2 Twin beds) and two bathrooms. Large families can take advantage of the extra Queen Sleeper Sofa available in the living room. This luxury condominium has the...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Terrace
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated 2nd floor direct ocean view condo with two bedrooms (1 King bed + 2 Twin beds) and two bathrooms. Large families can take advantage of the extra Queen Sleeper Sofa available in the living room. This luxury condominium has the white sand and turquoise sea of the most prestigious...
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    Seven Mile Beach, Grand Cayman KY1 1202
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Mi Casa, Su Casa, The Retreat at Rum Point1 / 24
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mi Casa, Su Casa is exactly what it sounds like, a home from home. This is a one bed, one bath 1039 sq foot condo with a large master bedroom (bamboo sheets), a good sized living area, a spacious kitchen and a bathroom (bamboo towels) with a bath/shower combo. Lovingly renovated in 2010 and again...
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    Rum Point, Grand Cayman KY1 1700
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    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
    About this property
    *** SUMMER SPECIAL — Join us this summer and receive 10% off PLUS indulge in the best Grand Cayman has to offer on land and sea with your choice of a half-day boat excursion to Stingray City; a private family cooking class and dinner; or a $750 in-villa spa credit toward the services of your...
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    Grand Cayman, Cayman Islands 10001
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Waterfront
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ONE BEDROOM DELUXE POOLSIDE CONDOMINIUM – 1100 SQ.FT. - 8 CONDOMINIUMS Full one bedroom deluxe condo with private bedroom with King size bed, full bathroom + 3/4 bathroom, living room and fully equipped kitchen. In the living room area there is a large entertainment center, which stows 2 full...
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    East End, Grand Cayman K1 1800
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'R' Retreat Guesthouse - gorgeous and very spacious with cozy ambience located in a quiet neighborhood of the well-known Sunrise Landing on the Canal. 'R' Retreat - the name says it all. This comfortable and spacious Sunrise Landing guesthouse is in a peaceful spot surrounded by the gentle sounds...
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    Savannah, Grand Cayman KY1 1011
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    View of the Ocean from every room / Pool1 / 9
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
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    • Ocean Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our new townhouse just 100 yards from the ocean! You can see the ocean from every room of the house. Living Room, Dining Room, Kitchen and both Bed Rooms. We enjoy our privately-owned home as a diving and vacation destination, properly named The Byrd Nest As we are Michael And Rachel...
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    Cayman Brac, Cayman Islands KY2 2101
    Holiday Rental House - 2 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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    Beachfront Winter Getaway at Resplendent Kaibo1 / 20
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Waterfront
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at the Kaibo Yacht Club Phase 2 in Grand Cayman's exclusive Cayman Kai area, this is a 2 bedroom/2 bathroom condo, recently refurbished and fully equipped. Sleeps up to 6 persons, with king size bed in master bedroom, full size bed in second bedroom and has a queen-sized sofa bed in living...
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    North Side, Grand Cayman KY11007
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Mountain Views
    • DVD Player
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Reach House sits on the very southeast side of Cayman Brac. A private house in a completely clean and safe environment. Cayman Brac is known as the Old Caribbean and is a quiet and tranquil paradise. Come and enjoy some time on this beautiful island. Our house comes fully equipped with...
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    Cayman Brac, Cayman Islands 11111
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly located condo on the world-renowned Seven-mile beach. This condo offers 2 bedrooms, and 2 full bathrooms including a sofa bed in the living room. This condo also includes an air-conditioned unit, fitted wardrobes, Wi-Fi, safety deposit box, fully equipped kitchen, TV and DVD player,...
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    West Bay, Grand Cayman KY1 1204
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Housekeeping Included
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spectacular Condo, is situated in the very heart of 7 mile beach, and has been upgraded for 2018. All freshly painted, new high end furniture and furnishings, new kitchen, and 3 large flatscreen TVs!! This 2 bedroom condo has beautiful views!!!! Amenities: Here is a short offerings of...
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    Location Information
    Seven Mile Beach, Grand Cayman KY1
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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