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George Town Holiday Vacation with Pools

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    C$1,431 Average
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    Travellers to George Town are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    18 Matching Rentals in George TownView all 29 rentals
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    Surfers Paradise Oceanfront on the 'New Seven Mile Beach'...come and relax !1 / 51
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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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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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Picture Perfect by Grand Cayman Villas and Condos1 / 18
    (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 April 22, 2016
    There were 10 of us - 3 young children included - and this place worked out really well for us.It was exactly as pictured in the photos. The house is very well located - a short...
    Reviewed February 13, 2016
    We've enjoyed this villa three years in a row because the house, the property, the setting and the location are near to perfect for us. The rooms are spacious; there's plenty of...
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    About this property
    Picture Perfect is the name given to this sunny oceanfront villa by its owner, a professional photographer. Located in South Sound, Picture Perfect is closer to Seven Mile Beach, the airport, and in-town restaurants than the homes located in Rum Point or Cayman Kai. Some of our guests opt not to...
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    Location Information
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Grandview, toes in sand1 / 30
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Hot Tub
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 25, 2018
    This was our first trip to Grand Cayman and it was amazing! The condo was very nice, well equipped, clean and in really good shape. Graham was great to communicate with and took...
    Reviewed March 2, 2018
    This condo is part of the Grandview complex, which has its own reviews and rental page that consists only of units managed by the main office. I’m assuming owners have the...
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    About this property
    Walk out from the apartment and within 3 steps (around 10 feet) you are on Seven Mile Beach with all that it has to offer. Protected cove on your doorstep, great for the little ones to get them into sea safely. The main part of the Grandview beach gives easy access to the water. Some good...
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    George Town, Grand Cayman KY1 1209
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Sprat Bay Luxury Villa1 / 24
    (8)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2019
    Lovely home conveniently located near 7 mile beach, shopping, restaurants and attractions. Sandy, the property manager, was so helpful, kind and available throughout our stay...
    Reviewed April 18, 2019
    This was our first time to the Cayman Island. The trip was a celebration of our 50th wedding anniversary. We wanted to spend a week with our kids and grandkids. This house was a...
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    About this property
    Ocean Front Villa with its own private beach and swimming pool located in South Sound. The villa is constructed on a 20,000 sq ft land in a tropical setting with tall palm trees. The living area is 6,000 sq ft has 3 living rooms, 6 bedrooms and 6 en-suite bathrooms sleeps up to 22 people. The villa...
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    George Town, Grand Cayman KY1
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Patio
    • Ocean Views
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Luna, a luxuriously intimate resort-style community nestled along the coastline just south of Seven Mile Beach. Inspired by Tuscan architecture, Casa Luna blends modern luxury living with an award-winning landscape design to create a secluded Caribbean oasis to call your very own....
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    Location Information
    George Town, Grand Cayman KY1 1100
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    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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    Location Information
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 18
    Direct Beachfront Condo,quiet,with pool and tennis1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 27, 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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    Location Information
    George Town, Grand Cayman KY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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 June 6, 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
    George Town, Grand Cayman KY1 1202
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    • Patio
    • Ocean Views
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning 3 bedroom townhouse, across three levels in an exclusive quiet and tranquil, gated community in South Sound across from the beach, the complex is gated as well as each property being gated. Modern furniture and decor throughout. Open plan living room, kitchen, dining room. Three private...
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    Location Information
    George Town, Grand Cayman KY1 1105
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Caribbean Paradise 91 / 31
    (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 July 14, 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 December 22, 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
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    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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    Location Information
    George Town, Grand Cayman KYI 1206
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    5TH NIGHT FREE- 6-Bedroom Beachfront w/ 150' Pool, 2 Hot Tubs and 2 Fire Pit1 / 45
    (9)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • 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 August 1, 2019
    I will start by saying the concierges Shamar Byrd and Alecia Davis were two of the most professional over the top concierges i have ever dealt with. i had questions and needed...
    Reviewed September 10, 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...
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    About this property
    *** Get your fifth night free this fall! Terms and conditions apply. See our website or contact us for details. *** Introducing Point of View, a magazine-worthy South Sound villa that helps you focus on what's important: untouched natural beauty, simple luxuries, and distraction-free moments with...
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    Location Information
    George Town, Grand Cayman KY1 1302
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    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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    Location Information
    George Town, Grand Cayman KY1 1109
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    5TH NIGHT FREE - Elegant 7 Bedroom Colonial Beach Estate1 / 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 July 14, 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 April 30, 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
    *** Get your fifth night free this fall! Terms and conditions apply. See our website or contact us for details. *** Luxury Cayman Villas proudly presents “Tatenda,” a colonial estate located in the prestigious community of South Sound on Cayman’s Southern Shores. Offering the most exclusive...
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    Location Information
    George Town, Grand Cayman KY1 1111
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 20
    Caribbean Paradise #121 / 22
    (11)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2019
    Close to stores, beach was nice but with sea grass. House was spacious for 2 senior couples. Beautiful view and nearby neighbors were quiet. BBQ needed updating to use.
    Reviewed June 9, 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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    Location Information
    George Town, Grand Cayman KY1 1202
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5TH NIGHT FREE - 5-Bedroom, Architectural Masterpiece on a Secluded Beach1 / 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 May 4, 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
    *** Get your fifth night free this fall! Terms and conditions apply. See our website or contact us for details. *** Paradise is all around you at Nirvana—a five-bedroom, four-bath architectural masterpiece featuring floor-to-ceiling vistas of the Caribbean Sea, layered Bohemian décor gathered from...
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    Location Information
    George Town, Grand Cayman 11302
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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