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Smoking Allowed Holiday Rentals in Cayman Islands

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    Travellers to Cayman Islands are booking December dates now. Secure your holiday home today, and have the perfect trip.
    15 Matching Rentals in Cayman IslandsView all 409 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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    Buttonwood Apartment - 3 King Beds, 2 Bath1 / 9
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Grand Cayman/Rum Point area, Beachfront Condo- sleeps 6 comfortably1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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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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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • 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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bluebell Room is a comfortable room at the Addison & Lee Cayman Villa, it has a Queen size bed with memory foam mattress, spacious closet, TV, mini-fridge, full-size own bathroom outside the bed room not en-suite More information The space The Addison & Lee Cayman Villa is a newly renovated home...
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    George Town, Grand Cayman KY1 1208
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Marigold (Queen Suite Deluxe + Kitchen) is a newly renovated room in the Addison and Lee Villa with a Queen size bed, full size en-suite bathroom, a sitting area with sofa with big screen TV and kitchenette. It has doors open to the pool and deck area. This room can accommodate up a maximum of 2...
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    George Town, Grand Cayman KY1 1208
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Spacious, Fully Furnished Family Friendly 2 bed Apt. with Ocean View  - Unit #41 / 16
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beauty of Grand Cayman extends far beyond the Seven Mile Beach strip and if you are looking for a true picturesque island escape, away from traffic, noise and the cosmopolitan scene, then I would like to invite you to Whittaker’s Suncoast Vacation Rentals – a picturesque island retreat that can...
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    Bodden Town, Grand Cayman KY1 1603
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Balcony
    • Washer
    • Hot Tub
    • Terrace
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a fixed week timeshare rental with Saturday check-in. A beachside paradise on one of the world's most beautiful islands, Morritt's Tortuga is a tropical paradise. Snorkeling just outside your door, with a complete diving and snorkeling program at the resort. Two stunning pools, one quiet &...
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    East End, Grand Cayman KY1 1800
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Iris Room (Queen Suite Deluxe) is a newly renovated room with a Queen size bed, full size en-suite bathroom, sitting area with sofa, TV and mini fridge. French doors open to pool and deck area. The Iris Room is one of seven bedrooms at the Addison & Lee Villa, a newly renovated, in a quiet...
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    George Town, Grand Cayman KY1 1208
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Orchid Room (King Suite Deluxe) is a Master suite in the Addison and Lee villa near Camana Bay. The room has a King size bed with memory foam mattress, en-suite bathroom, walk in closet, sitting area, TV, mini fridge and a balcony with view of the front garden. This is a spacious bedroom with...
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    George Town, Grand Cayman KY1 1208
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beauty of Grand Cayman extends far beyond the Seven Mile Beach strip and if you are looking for a true picturesque island escape, away from traffic, noise and the cosmopolitan scene, then I would like to invite you to Whittaker’s Suncoast Vacation Rentals – a picturesque island retreat that can...
    View all property information
    Location Information
    Bodden Town, Grand Cayman KY1 1603
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beauty of Grand Cayman extends far beyond the Seven Mile Beach strip and if you are looking for a true picturesque island escape, away from traffic, noise and the cosmopolitan scene, then I would like to invite you to Whittaker’s Suncoast Vacation Rentals – a picturesque island retreat that can...
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    Location Information
    Bodden Town, Grand Cayman KY1 1603
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Perfect Large Apartment for your Grand Cayman Vacation - Unit #31 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2019
    Apartment is amazing so much space and clean has all we needed in the apartment, towels for beach, snorkels, fins and beach chairs to borrow. Rental car is a must so you can...
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    About this property
    The beauty of Grand Cayman extends far beyond the Seven Mile Beach strip and if you are looking for a true picturesque island escape, away from traffic, noise and the cosmopolitan scene, then I would like to invite you to Whittaker’s Suncoast Vacation Rentals – a picturesque island retreat that can...
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    Location Information
    Breakers, Grand Cayman KY1 1603
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Housekeeping Included
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one steps onto this property the sight, sound of the ocean greets you. This 3 bed, 2 bath charming Cottage, which was once a private home, is tastefully furnished with many personal touches and sits perfectly amongst the landscaped grounds. The owner loves her garden which includes native...
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    North Side, Grand Cayman KY1 1103
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    *BEST RATE GUARANTEED-PLEASE ENQUIRE*Luxury 3 Bedroom Villas on Seven Mile Beach1 / 50
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2018
    We stayed one week at the grand view on seven mile beach. It was a lovely, safe, beachfront condo with views from 2 of the 3 bedrooms. Air conditioning worked great and kept...
    Reviewed 3 July 2018
    Our family of 5, consisting of 2 adults and 3 children, stayed in Unit 30 last week. It is an amazing unit, which is part of an amazing condo complex on beautiful Seven Mile...
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    About this property
    Welcome to the Caribbean Club, a luxurious and exclusive beachfront paradise located directly on the famous Seven Mile Beach in Grand Cayman. GENERAL VILLA FEATURES Every kitchen has beautiful granite tops, modern fixings and appliances and is fully stocked with utensils. All suites offer...
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    Location Information
    Seven Mile Beach, Grand Cayman 0000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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