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Holiday Rentals with Pools in George Town

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    Travellers to George Town are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in George TownView all 38 rentals
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    Oceanview/Poolside Condo on Seven Mile Beach1 / 15
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    10 feet from the beach, Grandview has a grand view1 / 32
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sprat Bay Luxury Villa1 / 24
    (6)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2018
    Our family of 6 adults and 4 children ages 10, 6, 5 and 2, spent ten wonderful days in this home. The kitchen was ideal for fixing large meals. The cabinets are fully stocked...
    Reviewed 29 May 2018
    This house was immaculate! It slept our group of 23 without feeling like we were on top of each other. The pool and views were amazing! The beach was literally steps from the...
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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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    KY1, George Town, Grand Cayman
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
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    Direct Beachfront Condo,quiet,with pool and tennis1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2018
    This Condo was awesome. Everything advertised and more... the comfort, king bed, open floor plan, stocked with daily necessities, tons of beach towels and we especially...
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    About this property
    Welcome to coral bay village, your beachfront paradise. Located right on a secluded beautiful white sand beach, close enough to georgetown and the airport for your convenience, but far enough to enjoy the quiet and beauty without the crowds and rowdiness of seven mile beach. For less than the price...
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    KY, George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Luxury Condo on Seven Mile Beach  - Regal Beach Club #4111 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Children's Pool
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Had the luxury of staying here for 4 nights. The condo is newly renovated and absolutely beautiful. New appliances and decor. Very comfortable. Location is perfect. Great pools...
    Reviewed 8 January 2018
    We had a wonderful stay, the condo was very clean and updated! Mark was very accommodating and made sure we had everything we needed.
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    About this property
    Beautifully updated to a high standard in September 2017 condo unit #411. This ground floor 2 bed 2 bath condo has views of the delightfully manicured gardens, pools and the world famous seven mile beach. 1 minute walk and you're on the glorious white sand looking at crystal clear water. 2...
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    KY, George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Spacious Luxury 3 Bedroom 3 1/2 Bath Townhouse fully furnished and appointed with all the supplies you will need for your vacation stay! Located in quiet community only 10 mins to George Town and 15 mins to Seven Mile Beach! Close to all major stores, shopping and many amazing restaurants....
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    KY1, George Town, Grand Cayman
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Surfers Paradise Oceanfront on the 'New Seven Mile Beach'...come and relax !1 / 50
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    My husband and I joined some friends for Pirate's Week, only a weekend, and enjoyed most of what this location has to offer! We sat down on the pool deck to enjoy the beautiful...
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    About this property
    Surfer’s Paradise is a beachfront coastline property on the south-west corner of Grand Cayman, where it is ideal for surfing and adjacent to South Sound a reef protected seawater Sound. Our bedrooms have names relating to surfing terminology: Hardcore, Stoked, Green Room, Goofy-foot and Banks....
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    0000, George Town, Grand Cayman
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Coral Sands Resort: 2-BR, Sleeps 6, Full Kitchen1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2016
    I exchanged my time share weeks to stay here in April 2016 with 3 friends, and I am very impressed. We were given Unit #1 which is water front. I love seeing the sunset right...
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    About this property
    Coral Sands Resort is a small resort located close to downtown Georgetown and within walking distance to shopping, restaurants, and nightlife. Enjoy a day at Seven Mile Beach just a short drive away, or relax at the resort's private beach. The resort also has a small pool. Pool view Direct access...
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    Location Information
    KY1 1202, George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rent Direct From The Owner and Save1 / 9
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Great location, you can enjoy peace and tranquility while at the same time easy access to anywhere on the island. The condo we stayed in was clean and beautiful. Everything was...
    Reviewed 1 August 2018
    Beautiful condo located about 50 feet from the sand. Everything in the condo appeared to be new. Many great restaurants a few minutes away. Yvonne was very easy to work with and...
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    About this property
    Caribbean Paradise #22 is an OCEAN VIEW condo located in beautiful, tranquil South Sound. Come to the Quiet Side of Grand Cayman. Decompress on our beautiful sand beach without the noise and distractions of 7 Mile Beach, which is 10 minutes away. Enjoy swimming, snorkeling, or just strolling on the...
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    NONE, George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    *** 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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    KY1 1202, George Town, Grand Cayman
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fixed week rental, 7 nights, Saturdays changeover only. Also known as Holiday Inn Resort Grand Cayman. Free shuttle to Seven Mile Beach, 5 min. One Bedroom Suite One king bed One bathroom Living room with sleeper sofa Dining room and full kitchen Iron, ironing board,...
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    KYI 1206, George Town, Grand Cayman
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Townhouse in The Tropics!  Well Appointed in Great Complex!1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Children's Pool
    • Balcony
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2018
    We loved the location of this spotless and spacious condo. It was very quiet and comfortable for sleeping with lots of space for 4 adults and a baby. The pools right outside the...
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    About this property
    3-story townhouse in very popular and family oriented complex. Gated community with 3 phases and 3 beautiful pools for your use. One of which is right outside your back door. The pool also has a great area for toddlers, which is about 1.5 feet deep. The complex also has 2 tennis courts and a...
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    KY1 1103, George Town, Grand Cayman
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Picture Perfect by Grand Cayman Villas and Condos1 / 24
    (8)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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 22 April 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 14 February 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
    *** 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!*** Picture Perfect is the name given to this sunny oceanfront villa by its owner who is also a professional photographer. Located in South Sound, Picture Perfect is...
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    KY1 1202, George Town, Grand Cayman
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    George Town Villas 1041 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2018
    A beautiful condo and very clean. The pictures are exactly what you get. Comfortable beds, plenty of pots and pans. Walking distance to bars, restaurants and stores. They...
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    About this property
    Welcome to the newly renovated ground floor, 2 bedroom unit at George Town Villas! Inside you will find big, sea-view windows where you see the beauty of the Caribbean waters. The open concept kitchen, dining and living area makes for the perfect place to gather after a sun filled day. The open...
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    KY1 1002, George Town, Grand Cayman
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Caribbean Paradise 91 / 12
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    This was a great property for our four adults and two children. The view is just stunning, and it's also convenient to the community pool. The pros: views, beach...
    Reviewed 22 December 2017
    We stayed here with two teens the first week of December. This location is the best. Close to Georgetown but not in it, grocery store a short drive down the road, a quiet...
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    About this property
    This standalone 3-bedroom beachfront villa—part of a resort/condo complex—is found in a residential area where many Caymanians make their home (or second home). The lovely neighbourhood of Caribbean Paradise, in South Sound, boasts a sense of community and a beach with impossibly soft white...
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    Location Information
    KY1 1202, George Town, Grand Cayman
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    WINTER SPECIAL - 6BR Oceanfront - 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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    About this property
    *** Stay 5 nights for the price of 4, or 7 nights for the price of 5, now through December 15, or January 5 through February 8. Terms and conditions apply. See our website for details. *** Introducing Point of View, a magazine-worthy South Sound villa that helps you focus on what's important:...
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    KY1 1302, George Town, Grand Cayman
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    7 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • DVD Player
    • Washer
    • Hot Tub
    • Grill
    • Air Conditioning
    • 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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    KY1 1202, George Town, Grand Cayman
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completed in 2012, this house is As Good As It Gets. Decorated from top to bottom by noted interior designers, the house was featured on the cover of Real Life Magazine last year and is one of the Showcase Properties on their website. This 5 bedroom, 5 bathroom beachfront home has it all: Living...
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    KY1 1109, George Town, Grand Cayman
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • 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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    Location Information
    KY, George Town, Grand Cayman
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 16
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    WINTER 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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    Amenities & Details
    • 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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    About this property
    *** Stay 5 nights for the price of 4, or 7 nights for the price of 5, now through December 15, or January 5 through February 8. Terms and conditions apply. See our website for details. *** Luxury Cayman Villas proudly presents “Tatenda,” a colonial estate located in the prestigious community of...
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    KY1 1111, George Town, Grand Cayman
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
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    Caribbean Paradise #121 / 22
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2018
    The place had a great location with plenty of room for the six of us. Lots of kitchen items like pots and pans, plates and silverware. The storage area by the stairs was perfect...
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    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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    KY1 1202, George Town, Grand Cayman
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    WINTER SPECIAL - 5BR Oceanfront Estate - Nirvana by Luxury Cayman Villas1 / 39
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    About this property
    *** Stay 5 nights for the price of 4, or 7 nights for the price of 5, now through December 15, or January 5 through February 8. Terms and conditions apply. See our website for details. *** Luxury Cayman Villas proudly presents 'Nirvana,', a one-of-a-kind, eco-chic oceanfront estate affording...
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    Location Information
    11302, George Town, Grand Cayman
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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