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Vacation Rentals in Grand Cayman, Cayman Islands

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified 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
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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236 Trusted Grand Cayman Rentals
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Cayman Islands, Grand Cayman, George Town Vacation...
2 Bedrooms, Sleeps 6
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You added Georgetown Villas Unit # 203 - Oceanfront Condo to your Saves list
from
$279
Per Night
Cayman Islands, Grand Cayman, George Town Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Georgetown Villas Unit # 303 - Oceanfront Condo to your Saves list
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$225
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added #1 Harbour Heights 2B2B ONE step to 7 Mile Beach! to your Saves list
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$315
Per Night
Also consider
Ultimate Oceanfront Penthouse W Unbeatable Views!!
$406 - $1,299 / night
3 Bedrooms, sleeps 7
2 Bathrooms
1B Condo on SevenMileBeach - CaymanReefResort #17
$200 - $400 / night
1 Bedroom, sleeps 4
1 Bathroom
Very Private Villa w/ Sandy Beach, Pool & Parrots
$550 - $850 / night
4 Bedrooms, sleeps 10
4 Bathrooms
#27 Harbour Heights: Beachfront Beauty, Sleeps 6
$315 - $490 / night
2 Bedrooms, sleeps 6
2 Bathrooms
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$250
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 3 Bathrooms, Sleeps 6
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You added $100 off April dates at Cayman's best kept secret. to your Saves list
from
$450
Per Night
On The Bay #311 , Old Man Bay
Cayman Islands, Grand Cayman, Old Man Bay Vacation...
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$276
Per Night
Tastefully decora... , Seven Mile Beach
Cayman Islands, Grand Cayman, Seven Mile Beach...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Tastefully decorated 2BR condo, direct walk to beach #7 to your Saves list
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$330
Per Night
Ocean-front 2BR... , Seven Mile Beach
Cayman Islands, Grand Cayman, Seven Mile Beach...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$330
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Cayman Conch Quest Beachfront Condo in Rum Point to your Saves list
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$215
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added "A Mid-Winter Night's Dream" - Direct Oceanfront!! to your Saves list
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$230
Per Night
On The Bay #104 , Old Man Bay
Cayman Islands, Grand Cayman, Old Man Bay Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$196
Per Night
Cayman Islands, Grand Cayman, East End Vacation...
1 Bedroom, 1 Bathroom, Sleeps 4
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You added 55 steps from your patio, across beach to the sea to your Saves list
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$159
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 3 Bathrooms, Sleeps 4
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You added Looking for endless Seafront views? Try SS 24! to your Saves list
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$260
Per Night
Cayman Islands, Grand Cayman, West Bay Vacation...
3 Bedrooms, 4 Bathrooms, Sleeps 7
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You added Divers Paradise Huge 3 Bed 3.5 Bath Townhouse to your Saves list
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$250
Per Night
Cayman Islands, Grand Cayman, North Side Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Cayman Stead, 2 BR, 2 bath,BEACH condo,sleeps 6 to your Saves list
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$275
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Three Little Birds -2BR+ Villa, Private Beach to your Saves list
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$360
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 3 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$480
Per Night
Cayman Islands, Grand Cayman, North Side Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Northern Exposure-Tranquility at the Oceans Edge to your Saves list
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$285
Per Night
Cayman Islands, Grand Cayman, North Side Vacation...
3 Bedrooms, 5 Bathrooms, Sleeps 8
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You added Caymanease A New Oceanfront Villa With A Pool to your Saves list
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$657
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
3 Bedrooms, 3 Bathrooms, Sleeps 10
from
$650
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 3 Bathrooms, Sleeps 6
from
$225
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 8
from
$425
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
3 Bedrooms, 4 Bathrooms, Sleeps 8
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You added Designer Villa, in Tranquil and Beautiful East End to your Saves list
from
$300
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 3 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Cayman Islands, Grand Cayman, Old Man Bay Vacation...
3 Bedrooms, 3 Bathrooms, Sleeps 6
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You added Cayman Paradise On the Bay- Ask for Fall Specials! to your Saves list
from
$250
Per Night
Cayman Islands, Grand Cayman, West Bay Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 4
from
$325
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Beachfront ground floor condo rental The Laurelei to your Saves list
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$220
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Sea Breeze/Rum Point/Retreat/Grand Cayman to your Saves list
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$200
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Beachfront, 7 Mil... , Seven Mile Beach
Cayman Islands, Grand Cayman, Seven Mile Beach...
2 Bedrooms, 2 Bathrooms, Sleeps 6
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You added Beachfront, 7 Mile Beach, Discovery Point Club to your Saves list
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$325
Per Night
Cayman Islands, Grand Cayman, East End Vacation...
Studio, 1 Bathroom, Sleeps 2
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You added 120 steps from beachfront balcony to Caribbean Sea to your Saves list
from
$119
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$420
Per Night
Caribbean, Cayman Islands, Grand Cayman Vacation...
2 Bedrooms, 2 Bathrooms, Sleeps 6
from
$150
Per Night
Cayman Islands, Grand Cayman, George Town Vacation...
3 Bedrooms, 3 Bathrooms, Sleeps 6
from
$473
Per Night
Escape in style – Grand Cayman beach villa and luxury condo rentals

With mile after mile of pristine beaches and clear turquoise seas, Grand Cayman vacation rentals take full advantage of their surroundings. Villas and condos feature beach-friendly comfort, private pools, bikes and tranquil island views. Our unbiased reviews say it best and give you confidence in your selection. “The location was perfect … the lagoon, kayaks, bikes, pool and Rum Point Beach….” And from a luxury condo vacation renter – “a little haven of tranquility. It is bright, clean, furnished to a great standard….”

Colorful, family-friendly island paradise

You will love the spirited blaze of color in the George Town capital and around the island. Perhaps perpetual sunshine demands the vibrant shades of purple, coral, sea green and mustard yellow that splash across island buildings. Groups, families and individuals enjoy all types of water adventures, from snorkeling and first class diving to turtle farm visits and simple beach picnics. Couples duck under the graceful casuarina trees for an exotic island cocktail along the more subdued Rum Point beach. The popular Seven Mile beach is close to everything and brimming with activity, so you’ll have no problem choosing the right tempo to suit your mood. Grand Cayman is a British territory and thriving financial center with over 600 international banks; so it’s easy to find many ways to contribute to the local economy. Pricey restaurants offer international cuisine, and local eateries deliver robust island fare with turtle, conch and Caribbean spices. Shopping choices mix duty-free luxury goods and fine jewelry boutiques with local specialty items and Cayman-esque souvenirs. Just be sure to remember your passport, now required of Caribbean-bound United States citizens.

From markets to bistros

The casual Market at the Grounds delivers a distinct Cayman atmosphere and taste. Enjoy home-cooked specialties, while you shop for traditional island crafts. Starvin’ Artists is a local artisan co-op with art, photography and crafts for every pocketbook. For a change from the many waterfront dining choices, you’ll find The Brasserie tucked away on Cricket Square in George Town. It’s a secret dining favorite with local corporate types, where customers enjoy the freshest of sea harvests, vegetables and fruits in a rich colonial setting.

Vacation rentals combine luxury, value and authentic island experience

Grand Cayman is not an inexpensive island destination, but you can avoid the high-end resort costs with your own luxury rental home. You’ll enjoy spacious living and the convenience of alternating meals cooked in your own villa kitchen with the pleasure of trying local restaurant choices. It’s the best of both worlds and one that will make you feel like a genuine islander!

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