Cayman Islands Ski In Ski Out Rentals

When heading to the mountains, few amenities rival the convenience of a Cayman Islands ski-in/ski-out vacation rental. Just put on your skis right outside your door and away you go. Owner Direct has compiled this list of Cayman Islands ski-in/ski-out accommodations to help you find the perfect retreat. From condos with a view to spacious chalets, we'll have you schussing down the slopes in minutes.

For your next ski holiday, book an Owner Direct vacation rental in Cayman Islands. We have 1 ski in ski out vacation rentals in Cayman Islands resorts. Stay in Cayman Brac, Grand Cayman, Carib Sands Beach Resort, Cayman Breakers, Kings Point or one of the other communities. Our extensive website is full of detailed information and descriptive photos of each property and our friendly customer service will help you each step of the way. Each owner sets their own price and our software immediately shows you the exact price for your requested dates. Book now before it's gone.

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1 Ski In Ski Out Vacation Rentals

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  • 3bed 2bath - Entire

    Cayman Islands: Duplex - left side
    3 BDR • 2 BA • Sleeps 8 • #246429
    170 to 192 USD/night Credit Card
    Spacious and comfortable 3 bedrooms, centrally located on the island of Grand Cayman. Suitable as a romantic getaway for couples, for business travelers with kids (over 2), spring breakers and vacationers. The Apartment is approximately 10 mins from the airport, public beaches, Shopping centers, gym and restaurants. The Apartment is licensed through the Cayman Islands Dep. Of Tourism and attracts a 13% tourist accommodation tax, plus 8.75% service fee. These will be charged upon check-in.
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  • Delightful Beachfront

    Grand Cayman: Kaibo Yacht Club: Condo in a complex
    2 BDR • 2 BA • Sleeps 6 • #112273
    200 to 300 USD/night Credit Card Paypal Star Rating
    Cayman Islands luxury ground floor condo nestled in a tropical paradise, on the sandy shores of Cayman Kai in the exclusive Rum Point area. Seventeen feet of glass doors face the water. Walk out the back screened patio onto the beach. Nicely furnished, secluded and relaxing... yet close enough to town for all other activity. Visit stingray city - tours from Kaibo or Rum Point. Kayak tours right from our beach. Kaibo Yacht Club bar & grill offers great food and drinks and elegant upstairs dining. Tourist activities abound throughout the island. 2 Twin beds can be converted into a King bed upon request.
  • Stunning Ocean Sunsets in

    Grand Cayman: Townhouse
    2 BDR • 2 BA • Sleeps 6 • #245440
    275 to 400 USD/night Credit Card
    Our Island House has recently had a complete interior renovation. All new furniture throughout including living room, dining room, and both bedrooms. From the moment you move in to the minute you depart, you'll have your own private home with all the creature comforts at your disposal. Kick off your shoes, and relax in a home away from home or play in the sea. Taste culinary delights and end your day with a romantic Caribbean sunset. Located in the heart of Rum Point on the north shore of Grand Cayman, this two-bedroom/2.5-bath home is ideal for a family or two couples. It features a swimming pool, deck, a lagoon with dock, and water views from both the two-story, screened-in porch and the bedroom balconies. Island House is set in landscaped gardens with white sand on the quiet waters of the lagoon just 150 feet from your back door. It's fully equipped with every comfort for an outstanding vacation in a contemporary tropical house. The famous Rum Point Beach is accessed by a sand path between white picket fences -- just a few steps from the front door. As you walk towards the beach, cool trade winds will quickly erase all thoughts of your job, commute, and bad weather at home. You'll see Australian pines with island parrots and tropical birds sitting on their feathery branches. This lovely home features lots of glass to take in the incredible views. Looking through a two-story wall of glass from the foyer, office/music room, and living room, you'll see the Caribbean Sea. Turn around, and you'll see the screened-in-lanai, backyard, and the lagoon beyond (about 50/100 feet) through 20 feet of sliding glass doors. Adjacent to the living room is the dining room and kitchen. Kitchen amenities include a coffeemaker, microwave, blender, rice cooker, and all the necessary cooking utensils. Off to the side is a closet with games and storage space, a half bath, and a laundry room with a washer, dryer, ironing board, and laundry supplies. Directly off the kitchen, the two-story, screened-in lanai features an informal dining area with a barbecue gas grill. Form the lanai you'll have an unobstructed view of the hand-raked, sand lawn, backyard with tropical tress and shrubs -- leading to the pool (within 50 feet), boat dock, and lagoon shoreline. This Island House offers two master bedroom suites upstairs. Each bedroom has a full private bathroom with shower and bath, and sliding glass doors opening onto a private screened-in-balcony. Both rooms have a lagoon view. And both have walk-in-closets, a ceiling fan, TV, a clock radio, and individual air-conditioning. One bedroom is equipped with a king-size bed and dresser, while the other bedroom has two double beds and dresser. Located on the quiet North Side of the island, a 45-minute drive from the busy city of Georgetown, it has the famous Rum Point Beach only a few steps from your front door, a fresh water pool only a few steps from your back door, an inlet lagoon that exits in to the Caribbean Sea, many activities for adults and children, many very good restaurants, a complete water facility 'Red Sport Sails' at Rum Point Beach which offers any water sport you could want, a convenience store within a short distance and some of the World's finest neighbors. Grand Cayman's Best Kept Secret!
  • New Luxurious Condo at

    Cayman Brac: Kings Point: Townhouse in a complex
    2 BDR • 3 BA • Sleeps 6 • #208289
    200 to 200 USD/night Credit Card Paypal Pet Friendly
    As you arrive to our townhouse at this new complex, you will be welcomed by the lush exotic greenery. Inside our home, you feel the coolness of the fresh air from the fans and air conditioning. Your feet touch the double glazed Italian porcelain tiles and melt you into your experience. Such luxury. Everything that you could want to make your vacation the best. Exhausted from your flight, you head right up the carpeted stairs to find your King bed waiting for you in the Master Bedroom. But to sleep. No. One step out to the balcony and the fragrant tropical air, the swimming pool and hot tub beckon you to explore further. Quickly changing into your swim suit, you dash downstairs, thru the main floor and out the patio door just a few steps to the awaiting swimming pool and hot tub. Shall you stop by the four awaiting hammocks on the way down to the ocean. Later. There it is. Just steps from your door ~ THE OCEAN. With a cut, stairs and ladder, there is easy access into the ocean right in front of our home. Finally, back into the home. Well furnished with everything that you could want. Livingroom with large sofa that pulls out to a Queen bed, large overstuffed chair and ottoman, end tables, coffee table and recreation centre with large 40 inch television and blu ray player. A welcome binder is there for you to use as a guide to this island, full of excellent ideas of things to do, where to dive or snorkel, restaurant suggestions and so much more. There beside the dining room is a large shelving unit filled with jigsaw puzzles, books, DVDs, board and card games and everything you could want in the event of a rainy day. A laundry closet with washer and dryer and two dryer racks for fresh air drying and complete with large ironing board and iron. A powder room is downstairs and two full bathrooms upstairs all with high end fixtures. Ah, the kitchen. I didn’t come on vacation to cook, is the comment that I hear most often. And yet ~ look at this beautiful kitchen, decked out with everything that you could possibly want. Lots of dishes, glasses, cutlery, pots and pans, Pyrex and Corning Ware, every small appliance that you could want . . . all this awaits you as you prepare the local fresh catch of the day. And back upstairs at the end of the day. Ah, but just a moment out on the balcony, sitting back to watch the stars. Or shall we soak in the hot tub first. Or shall we lounge in the large bath tub with the beautiful waterfall spout. Relax and fall asleep on the large King Size pillow top mattress with four large King pillows. Or were you relegated to the back bedroom. Not to worry, all windows have views of the ocean and the bluff. The second bedroom has a nice Queen bed with the same pillow top mattress, and another four King pillows. And yes, it has its own private bathroom with large shower with rain shower head. Luxury throughout. Daily rate is $200 USD, double occupancy, minimum 7 days. LUCKY 13!!! Book 14 nights, pay for 13.. Three weeks ~ $3000 US$-double-occupancy Four-weeks~$3600US$-double-occupancy Longer-rentals 1 - 5 months is $3600 USD/mo, includes wi-fi, power, water. CI tax of 13% if applicable, damage deposit $500. OR-$1800US$-per-month-includes-wi-fi-but-does-not-include-utilities. Rental 6 - 11 months $1500 USD, Rental 12 months+ $1400 USD/mo. Includes wifi, does not include other utilities. Tax not applicable. WELCOME AND ENJOY!
  • Cayman Brac, 1 Bedroom

    Cayman Brac: Carib Sands Beach Resort: Condo in a complex
    1 BDR • 1 BA • Sleeps 2 • #15350
    142 to 150 USD/night Credit Card Paypal
    The complex features a large, beach-front pool area, landscaped grounds, an exercise room and a dock pavilion which offers exceptional views of Cayman Brac's spectacular sunsets. The unit features central air conditioning, ceiling fans and cable television. The kitchen is equipped with full-size appliances, microwave and coffee maker for your convenience. Ground floor units have a private poolside patio. The bedroom is spacious with a queen-sized bed, large closet, night tables and chest-of-drawers. Ceiling fans in all rooms. Patio doors open from the living room to a private, pool-side patio Coin-operated washers and dryers available to guests. Double-sized Murphy bed in the living room.
Experience the difference, no waiting
 
Experience the difference, no waiting
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International Rentals
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