Vacations in the Cayman Islands

Vacations in the Cayman Islands

2 travellers

KAYAK searches hundreds of travel sites at once for vacation package deals in the Cayman Islands

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals
Tips
Vacation information

Cheap the Cayman Islands package deals

Discover the best prices by selecting your travel dates on KAYAK.
Go to map

Search by stars

2+ stars3+ stars4+ stars5 stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 678 - C$ 1,897C$ 1,897 - C$ 3,114C$ 3,114 - C$ 4,332C$ 4,332 - C$ 5,549C$ 5,549+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular the Cayman Islands flight and hotel deals

Show all
Regal Beach Club - George Town - Balcony
Regal Beach Club - George Town - Balcony
Regal Beach Club
9 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,339
Oceanfront Condo on Seven Mile Beach - George Town
Oceanfront Condo on Seven Mile Beach - George Town
Oceanfront Condo on Seven Mile Beach
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,167
Holiday Inn Resort Grand Cayman by IHG - George Town - Pool
Holiday Inn Resort Grand Cayman by IHG - George Town - Pool
Holiday Inn Resort Grand Cayman by IHG
7.8 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 776
One Canal Point - George Town - Pool
One Canal Point - George Town - Pool
One Canal Point
10 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 804
Cayman Luxury Rentals At One Canal Point - George Town - Pool
Cayman Luxury Rentals At One Canal Point - George Town - Pool
Cayman Luxury Rentals At One Canal Point
9.3 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 967
Kimpton Seafire Resort + Spa - West Bay - Living room
Kimpton Seafire Resort + Spa - West Bay - Living room
Kimpton Seafire Resort + Spa
9.7 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,125
The Grand Caymanian Resort - George Town - Pool
The Grand Caymanian Resort - George Town - Pool
The Grand Caymanian Resort
7.4 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 862
Villas of the Galleon - George Town - Living room
Villas of the Galleon - George Town - Living room
Villas of the Galleon
9.4 Wonderful
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,337
Governors Village - George Town - Bedroom
Governors Village - George Town - Bedroom
Governors Village
9.2 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 790
Hotel Indigo Grand Cayman - West Bay - Bedroom
Hotel Indigo Grand Cayman - West Bay - Bedroom
Hotel Indigo Grand Cayman
9.6 Wonderful
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
C$ 948
Grand Cayman Marriott Resort - George Town - Bar
Grand Cayman Marriott Resort - George Town - Bar
Grand Cayman Marriott Resort
8.3 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
C$ 1,051
Prime Sunset Cove Condo - George Town - Beach
Prime Sunset Cove Condo - George Town - Beach
Prime Sunset Cove Condo
Free Wi-Fi
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,421
Shangri-La Boutique Bed & Breakfast - West Bay - Dining room
Shangri-La Boutique Bed & Breakfast - West Bay - Dining room
Shangri-La Boutique Bed & Breakfast
9.4 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
C$ 709
The Westin Grand Cayman Seven Mile Beach Resort & Spa - George Town - Patio
The Westin Grand Cayman Seven Mile Beach Resort & Spa - George Town - Patio
The Westin Grand Cayman Seven Mile Beach Resort & Spa
8.3 Very good
Parking
Pool
Pet friendly
Spa
Boston Logan Intl
Meals not included
3 nights + flight
C$ 1,139
The Ritz-Carlton Grand Cayman - George Town - Balcony
The Ritz-Carlton Grand Cayman - George Town - Balcony
The Ritz-Carlton Grand Cayman
9.3 Wonderful
Parking
Free Wi-Fi
Pool
Pet friendly
London
Meals not included
3 nights + flight
C$ 1,547
Hampton by Hilton Grand Cayman Seven Mile Beach - George Town - Lounge
Hampton by Hilton Grand Cayman Seven Mile Beach - George Town - Lounge
Hampton by Hilton Grand Cayman Seven Mile Beach
8.5 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Boston Logan Intl
Breakfast
3 nights + flight
C$ 678

Last minute vacation packages to the Cayman Islands

Show all
Blue Paradise - George Town
Blue Paradise - George Town
Blue Paradise
9.7 Wonderful
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
C$ 1,058
Southwinds Studio - East End - Beach
Southwinds Studio - East End - Beach
Southwinds Studio
7.5 Good
Parking
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
C$ 1,130

When to book a vacation in the Cayman Islands

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Tips for finding the Cayman Islands package deals

  • There are loads of types of vacations in the Cayman Islands and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travellers: Top vacation C$ 1,090; Family vacation C$ 1,020; Romantic vacation C$ 1,718.

Where to stay in the Cayman Islands

Our map will help you find the perfect place to stay for your vacation in the Cayman Islands by showing you the exact location of each hotel.

Everything you need to know for your vacation in the Cayman Islands

the Cayman Islands vacation information

Top vacation (Flight+Hotel)C$ 1,090
Family vacation (Flight+Hotel)C$ 1,020
Romantic vacation (Flight+Hotel)C$ 1,718

the Cayman Islands vacation: Search the Cayman Islands vacation packages on KAYAK. KAYAK is a travel tool that searches the Cayman Islands trips on hundreds of travel sites to help you find the the Cayman Islands package that suits you best. Discover the Cayman Islands deals now and book your the Cayman Islands flight and hotel today.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.