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Cayman Islands Vacation Rentals

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Contact Manager
Nightly rate from
$250
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 2
Bathrooms: 2
Mango Kai is nestled on a quiet cove amid lush tropical foliage, this is the perfect place for your family vacation or romantic get-away. Complimentary ...
  • Nightly
    $250 - $375
  • Weekly
    $1,750 - $2,625
  • Monthly
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Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
A Truly Spectacular Private Luxury Villa Home Northeast Coast - Grand Cayman Fishbones is the type of Caribbean home you see in movies or featured in luxury ...
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  • Weekly
    $3,600 - $6,300
  • Monthly
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Contact Manager
Nightly rate from
$225
Management: Professional
Property: Condo/Apartment
Bedrooms: 1, sleeps 4
Bathrooms: 1
The Pools #1 Luxury Island Getaway, Cayman Kai, North Shore, Grand Cayman, Cayman Islands, Caribbean (Near Rum Point) Accommodations: Condominium - 1 ...
  • Nightly
    $225 - $285
  • Weekly
    $1,400 - $2,200
  • Monthly
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Contact Manager
Nightly rate from
$225
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 3
Welcome to the Sea Cliff Resort, Grand Cayman. Leave the weeks and weeks of endless snow, sleet and freezing rain far behind. Your dream vacation in the ...
  • Nightly
    $225 - $325
  • Weekly
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  • Monthly
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Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
Beach front tranquility with a touch of Caribbean class. Designed by John Doak and built in a French West Indian style this spectacular beachfront property ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
The New Cayman Breeze Now has complimentary Wireless, High Speed Internet DSL for our Mobile Guests! Promotion: Free iPod Shuffle with every 7 day or more ...
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Contact Manager
Nightly rate from
$550
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
3 Bed 2 Bath Third Floor Minimum Stay: 3
  • Nightly
    $550 - $725
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$425
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
2 Bed 2 Bath Second Floor Minimum Stay: 3
  • Nightly
    $425 - $625
  • Weekly
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Contact Manager
Nightly rate from
$425
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
This unit is right on the beach with some fun murals to make you feel like you are always in the Caribbean Minimum Stay: 3
  • Nightly
    $425 - $625
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$350
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
This second floor unit has incredible Ocean Views and located overlooking our garden and pool straight out to the beautiful blues of the Caribbean. Minimum ...
  • Nightly
    $350 - $550
  • Weekly
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  • Monthly
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Contact Manager
Nightly rate from
$300
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Welcome to Venezia! Northside, Grand Cayman A luxurious, one of a kind private, ocean front Villa in the Cayman Islands located on the quite north side of ...
  • Nightly
    $300 - $360
  • Weekly
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Contact Manager
Nightly rate from
$625
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
Welcome to Windward Cove The Best Kept Secret in Grand Cayman Brand New 12' by 25' Oceanfront Swimming Pool Come to Our Beachfront Paradise on an Acre of ...
  • Nightly
    $625 - $770
  • Weekly
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Contact Manager
Nightly rate from
$200
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Welcome to 7 Up! This new (2006) 2 bedroom 2 bathroom waterfront Condo at Kaibo Kai in Rum Point, is decorated in a beautiful, clean Balinese style theme and ...
  • Nightly
    $200 - $250
  • Weekly
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Contact Manager
Nightly rate from
$575
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 12
Bathrooms: 3
Kai Conut is located on the Northside of the island in "Cayman Kai" near Rum Point. Offering 4 bedrooms a den and 3 baths ; Kai Conut sleeps 12 people ...
  • Nightly
    $575 - $1,215
  • Weekly
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Contact Manager
Nightly rate from
$235
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 2
Bathrooms: 2
Welcome to Northern Exposure, privately owned and managed condominium complex on the beautiful oceans edge on the pristine northern coast of Grand Cayman. ...
  • Nightly
    $235 - $350
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Cayman Islands Vacation Rental Advice
Posted by Mama2twocuties, Oct 27, 2009
... use and two weeks of vacation left, so ... ... We will not have a rental car either. Can you suggest any places walking distance to the Marriott that we can eat at? From reading the reviews, it looks like the restaurants at the hotel will be out of our price range ... more
Posted by Testudo, Oct 27, 2009
... t want to have a rental car and/or you need to be closer to a variety of moderately-priced fast-food type restaurant options to keep the family fed (e.g. the name-brands Subway, KFC, Wendy's, Burger King, Pizza Hut, and good "local" options like Chicken-Chicken ... more
Posted by filter14, Oct 27, 2009
... don't see a problem with it if that's what you want :) but there are also a bunch of little places that are more like cafes that serve at least breakfast and lunch plus 'treats'. You won't have to feel like you're settling for a subpar vacation ... more
Posted by zinnia7, Jul 28, 2009
... and like our beach/dive vacations to be ... ... like a Camry. Almost every rental car you see has the company’s logo sticker on the back bumper. This one did not. I swear this was someone’s personal vehicle that they borrowed because they ran out of cars. Fortunately it ... more
Posted by Testudo, Jul 28, 2009
... Child Care Expert for Grand Cayman if you're game. I'm thinking you may want to try Little Cayman or the East End once baby is a bit older and child care is not a priority. Could be more of what you usually look for in a dive vacation ... more
Posted by zinnia7, Nov 9, 2009
... and like our beach/dive vacations to be a bit more rustic. With all the strip malls and traffic I really felt like I was in Florida. I notice you are the destination expert for Anguilla - so you probably know exactly what I'm talking about. Grand Cayman did not ... more
Posted by NorthSideSue, Oct 23, 2009
It is a relatively new rental, so I would be surprised if you find someone who has stayed there. I had to do a google search since the name was not familiar. Looks very nice. The pool is surely shared by the other villas. ... more
Posted by TravelChild, Oct 24, 2009
... Kayaks leave from teh South Sound dock and they seem to go as far as Prospect Pt., so kayaking could be good. There is also the historical Watler cemetary near the rental. Location wise, it is about a 15 min drive to SMB, about 3 minutes to Hurley's supermarket ... more
Posted by CayManTA, Nov 2, 2009
I can't blame you for choosing the north coast area - being a Rum Point aficionado-turned-condo-owner there! It's a great vacation location. ... more
Posted by LuvGC, Oct 28, 2009
... point on all clear. Car Rental – We rented from Hertz as they guaranteed a child safety seat and the rate was competitive after AAA discount. The care itself was a Ford Focus with 85,000 miles on it – a piece of junk but it ran fine and the AC worked ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns