image of Cayman Beach

Experience Your Cayman Paradise

Your Perfect Cayman Vacation Rental

Book Direct for Best Rates and Services

Your Perfect Grand Cayman Vacation

Cayman Vacation has over 30 years of experience arranging perfect Grand Cayman Island Luxury Vacations serving over 100,000 vacation rental clients. With Cayman Vacation, you will receive friendly, professional and personalized boutique service, which leverages our in-depth knowledge of the Cayman Islands. Our attention to excellence assists you in choosing the very best Cayman Islands vacation accommodation to meet your specific requirements.

Choose from over 300 Grand Cayman condominiums, private villas and exclusive luxury estate homes. Grand Cayman accommodations range from 1 to 8 bedroom properties, perfect for honeymooners, family groups, reunions and wedding parties. Our hand selected properties are ideally located all over Grand Cayman. We personally know each property featured, helping you decide on the best option for your personalized Cayman Island Vacation.

All of our properties meet the Cayman Islands Department of Tourism stringent health cleaning protocols and contactless entry.

Book your travel insurance, grocery delivery service, water sports activities, personal in-villa Chef and mobile Masseuse online right along with your accommodations!

image of Cayman Beach resorts and destination

Resorts and Island Destinations

image of Seven Mile Beach Cayman

Seven Mile Beach

image of East End Cayman

East End

image of Caiman Kai

Cayman Kai

image of North Side Cayman

North Side

image of  Rum Point Cayman

Rum Point

image of South Sound & Bodden Town Cayman

South Sound & Bodden Town

image of Private Luxury Homes in Cayman

Private Luxury Homes

villa resort in Cayman Island


West Bay in Cayman Island

West Bay

image of Cayman Activities on the Sea

Book Your Activities

image of Cayman Island Map

Search Properties By Name

image or Property in Cayman

Guest Reviews

image of deals in Cayman Island


image of list your property in Cayman Island

List Your Property

image of Cayman sunset sea view


image of oversight in Cayman Island

Cancellation Policy

RedSky Travel Insurance logo

image of grocery and delivery services

Grocery Delivery Services

image of property pals

image of dad with kid on the beach

Empty Suitcase Rental

image of aqua watersports in Cayman Island

Aqua Watersports